N8S

Publications

A 11 101 7Efi34E NATL INST. OF STAND & TECH R.

A11105 042306

NBSIR 79-1777

A Compendium of Gas Phase

Basicity and Proton Affinity

Measurements

K. N. Hartman*, S. Lias, P. Ausloos, H. M. Rosenstock*,

S. S. Schroyer*, C. Schmidt*, D. Martinsen**, and G. W. A. Milne***

National Measurement Laboratory

National Bureau of Standards

Department of Commerce

Washington, D.C. 20234

*lon Energetics Data Center

National Bureau of Standards

Department of Commerce

Washington, D.C. 20234

**Fein-Marquart Associates

Baltimore, MD 21212

***National Heart Lung and Blood Institute

National Institutes of Health

Bethesda, MD 20205

April 1979

Issued July 1 979

This work was supported in part by the:

National Heart, Lung, and Blood Institute

National Institutes of Health

Bethesda, MD 20205

wtrmv <rt S*ani

* SEP ? 0 1973

NBSIR 79-1777

« *

* . , -

. f A COMPENDIUM OF GAS PHASE

BASICITY AND PROTON AFFINITY

MEASUREMENTS

K. N. Hartman*, S. Lias, P. Ausloos, H. M. Rosenstock*,

S. S. Schroyer*, C. Schmidt*, D. Martinsen**, and G. W. A. Milne***

National Measurement Laboratory

National Bureau of Standards

Department of Commerce

Washington, D.C. 20234

*lon Energetics Data Center

National Bureau of Standards

Department of Commerce

Washington, D.C. 20234

**Fein-Marquart Associates

Baltimore, MD 21212

***National Heart Lung and Blood Institute

National Institutes of Health

Bethesda, MD 20205

April 1979

Issued July 1 979

This work was supported in part by the: National Heart, Lung, and Blood Institute

National Institutes of Health

Bethesda, MD 20205

U S. DEPARTMENT OF COMMERCE, Juanita M. Kreps, Secretary

Jordan J. Baruch, Assistant Secretary for Science and Technology

NATIONAL BUREAU OF STANDARDS, Ernest Ambler, Director
-

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•; .

*

'

'

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FOREWORD

The National Standard Reference Data System was established

in 1963 for the purpose of promoting the critical evaluation and

di ssem i nat i on of numerical data of the physical sciences. The

program is coordinated by the Office of Standard Reference Data

of the National Bureau of Standards, but involves the efforts of

many groups in universities, government laboratories, and private

industry. The primary aim of the program is to provide

compilations of critically evaluated numerical data. These

tables are published in the Journal of Physical and Chemical

Reference Data , the various publication series of the National

Bureau of Standards, and through other appropriate channels.

The present report consists of tables of data on gas phase

basicity and proton affinity of molecules. It represents a contribution from the Ion Energetics Data Center, prepared in

collaboration with staff of NHLBI, NIH and Fei n-Marquart

Associates. Support for the preparation of these tables has been

provided by the National Heart, Lung, and Blood Institute and the

Office of Standard Reference Data

David R . L i de , Jr.

Chief, Office of Standard

Reference Data

l
ABSTRACT

Numerical values of experimental measurements, calculations

and estimations of gas phase basicities and proton affinites are presented. Where appropriate they are recalculated to common

values for the proton affinity of ammonia and the heat of

formation of the proton. The annotated information is ordered by

molecular formula following the Hill System. Indices are given

to permit location of information by numerical value of the

measurement (s) , the compound formula, name and synonym, and CAS

Registry Number. The literature coverage is essentially complete

through 1977.
TABLE OF CONTENTS

1. INTRODUCTION iv

1.1 The Data Base iv

1.2 Definitions and units iv

1.3 Standard states, conventions, and reference values... v 1.4 References vii

2. THE MEASUREMENT TECHNIQUES viii

2.1 Absolute measurements viii

2.2 Equilibrium measurements ix

2.3 Bracketing measurements x 2.4 Calculations and estimates, xi

2.5 References xi

3. ORGANIZATION OF THE INFORMATION xiii

4. TABLE OF MEASUREMENTS IN MOLECULAR FORMULA ORDER 1

5. GAS PHASE BASICITY INDEX 476

6. PROTON AFFINITY INDEX 482

7. CAS REGISTRY NUMBER INDEX 489

8. MOLECULAR FORMULA INDEX 497

9. COMPOUND NAME INDEX 503

iii
1. INTRODUCTION

1 . 1 The Data Base

The present compendium tabulates all experimental

measurements of gas phase basicities and measurements or derived values of proton affinities available up to the end

of 197?. This compilation was carried out for the NIH-EPA

CIS project which is developing a comprehensive chemical data

base for the use of workers concerned with research on environmental and health problems and related areas. The

numerical information presented here is also accessible and

searchable by computer through the NIH/EPA Chemical

Information System (CISM1).

1.2 Definitions and units

The gas phase basicity (GB) of a molecule CM) is defined

as the negative of the Gibbs free energy change for the

process

H + H

+

-v MH

+

and the proton affinity (PA) is defined as the negative of

the enthalpy change for the same process.

PA(M) = AH^CM) + AH . (H+

) - AHj. (MH+

) r r f

For completeness* the temperature has to be specified. It is

generally desired to evaluate the quantity at room temperature. Occasionally experiments are carried out at

high temperatures (e.g. 600 K or at undefined temperatures

(threshold measurements)), and for these it is necessary to

apply the appropriate thermochemical corrections or threshold

interpretations.

iv
From the relation AG = AH - TAS -the proton affinity can

be determined from the gas phase basicity if the temperature

and the entropy change of the process are known or can be

estimated.

The unit in most widespread use is the kcal/mol and this

unit is adopted throughout. It is related to the recommended

SI unit by 1 kcal = 4 . 1840 kJ, exactly.

1.3 Standard states, conventions, and reference values

The process

M + H

+

-* MH

+

makes no reference to an electron and no difficulties arise

if the heats and free energies of formation of all species

are defined with the same ionic standard state.

Unf ortunately this has not always been the case.

Hi stori cally, the community determining ion heats of

formation by threshold measurements have assumed the

convention that the electron is at rest (as it surely is at

threshold) and that it remains at rest even when deducing

finite (or room) temperature heats of formation of the ions.

This convention is also adopted in the two major compilations

of gaseous ion thermochemistry (2,3).

The two principal compilations of neutral thermochemi stry

(4,5) assign to the electron a classical heat capacity, Cp,

of 5/2 R. Thus at room temperature the heats of formation of

all ions will be larger than those in, for example Energetics

of Gaseous Ions (GIE) (3) by an amount equal to

298.15

/ CpdT = - RT = 1.481 kcal/mol

0

2

v
Calculations of proton affinities using room temperature ion

heats of formation from threshold measurements as compiled

and evaluated in Energetics of Gaseous Ions (3) and the

proton heat of formation as given in the NBS Tech Note 270

series (4) or the JANAF tables (5) will be in error (too

large) by this amount. Wherever the original reference

quoted proton affinity values were in error for this reason, we have made the appropriate correction. When the heat of

formation of the ion M

+

, is defined according to the GIE

convention, the value for the heat of formation of the proton

at 298.15 K is 365.7 kcal/mol. This subject is discussed in

detail in a recent review article (6).

A major part of the measurement base consists of relative

measurements which can be put on an absolute basis by

relating to a small number of absolute values.

Unfortunately, the magnitude of some of the absolute values

is still in doubt. For instance, many of the extensive

scales of proton affinity ladders which have been published

(7,8) have ultimately been related to the heat of formation

of t~C4H9 + as a primary standard, although the values are usually cited relative to the proton affinity of a secondary

standard, ammonia. At the time the present compilation was carried out, the latter value was considered to be

established at 202.3 kcal/mol (6), and it is this number

which is used as the standard for the values cited here

.

More recent redetermi nat i ons of the heat of formation (9,10)

and ionization potential (11) of the t-butyl radical, as well

as additional information on the entropy change associated

with the deprotonation of t-C4H9 + (12), have resulted in a revised estimate that the proton affinity of ammonia is

vi
greater than or equal to 207.0 kcal/mol (6). Thus, the

absolute values of proton affinities given here based on relative AG measurements and expressed "relative to ammonia"

are, according to the most recent information, too low by at

least 5 kcal/mol. In this and other cases we have indicated

the species to which the relative measurement is referred, so that readjustment can be made as additional information

becomes available.

1 . A References

1. S. R. Heller, G. W. A. Milne, and R. J. Feldmann, "A

Computer Based Chemical Information System," Science 195, 253

C 1977) .

2. J. L. Franklin, J. G. Dillard, H. M. Rosenstock, J. T. Herron, K. Draxl, and F. H. Field, "Ionization Potentials,

Appearance Potentials, and Heats of Formation of Gaseous

Positive Ions," NSRDS-NBS-26 , June 1969.

3. H. M. Rosenstock, K. Draxl, B. W. Steiner, and J. T. Herron, "Energetics of Gaseous Ions," J. Phys. Chem. Ref.

Data 6 Supplement 1 (1977).

A. D. D. Wagman, et al, "Selected Values of Chemical

Thermodynamics Properties," MBS Technical Note 270-3, January

1968, and subsequent Tech Notes in this series.

5. D. R. Stull and H. Prophet, "JANAF Thermochemical Tables,"

Second Edition, NSRDS-NBS-37 , June 1971 and supplements

published in J. Phys. Chem. Ref. Data.

6. S. Lias, "Thermochemistry of Polyatomic Cations," in

"Kinetics of Ion-Molecule Reactions," (P. Ausloos, ed.)

Plenum Press, New York, pg. 233.

7. J. F. Wolf, R. H. Staley, I. Koppel, M. Taagepera, R.

vii
T. Mclver, Jr.» J. L. Beauchamp, and R. W. Taft, "Gas

Phase Basicities and Relative Proton Affinities of Compounds

between Water and Ammonia from Pulsed Ion Cyclotron Resonance

Thermal Equilibria Measurements," J. Am. Chem. Soc. 99,

54 1 7 ( 1977).

8. R. Yamdagni, and P. Kebarle, "Gas Phase Basicities and

Proton Affinities of Compounds between Water and Ammonia and

Substituted Benzenes from a Continuous Ladder of Proton

Transfer Equilibria Measurements," J. Am. Chem. Soc. 98,

1320 (1976).

9. W. Tsang, "Evidence for Strongly Temperature-Dependent

A-factors in Alkane Decomposition and High Heats of Formation

for Alkyl Radicals," Int. J. Chem. Kinetics 11, 820

( 1978) .

10. M. Rossi and D. M. Golden, J. Am. Chem. Soc. submitted

for publication.

11. F. A. Houle and J. L. Beauchamp, "Photoelectron

Spectroscopy of Methyl, Ethyl, Isopropyl, and Tert-Butyl

Radicals. Implications for the Thermochemistry and

Structures of the Radicals and their Correspondi ng Carbonium

Ions," J. Am. Chem. Soc.» in press.

12. P. Ausloos and S. G. Lias "Entropy Changes for the

Protonation of Alkenes," J. Am. Chem. Soc. 100, 1953

( 1978)

.

2. THE MEASUREMENT TECHNIQUES

2.1 Absolute measurements

These are generally based on measurement of the heat of

formation of a proton-conta i n i ng species by a threshold

viii
process, such as

H

2

C> 2 + hv -v H0

2

+ + H + e

From the threshold energy of this process and the heats of

formation of the neutral atomic and molecular species one can deduce heat of formation of H02+

> and by further

stra i ghtf orward calculation the proton affinity of molecular

oxygen. In actual practice considerable care has to be

exercised to establish the temperature to which the heat of

formation refers. Threshold measurements leading to more or less accurate absolute values have been carried out by

photo i on i zat i on (PI), monoenerget i c election impact (EM) and

conventional electron impact (El) techniques. The accuracy

of these techniques has been comprehensively discussed in a recent review article (1).

2.2 Equilibrium measurements

From a determi nat i on of the proton transfer equilibrium

constant for

AH

+ + B ^ A + BH

+

one can determine the Gibbs free energy change of the

reaction. This gives the basicity difference between the two

compounds. In order to determine the proton affinity

difference it is necessary to determine the entropy change of

the reaction. The most direct and unambiguous method is to

measure the equilibrium constant as a function of

temperature, which yields the proton affinity directly from

the Van't Hoff relation

din K

ecr d (1/T) R
So far for pro-ton transfer equilibria this has only been

performed in a few instances, with varying degrees of success

(2). Most estimates of the relative proton affinity are based on assumptions about the entropy change. These range

from consideration of symmetry changes in the reaction, to

reasoning by analogy, to the assumption that the entropy

change is zero. The method or the assumptions made for

obtaining a value for AS are indicated in this compendium for

each determination.

Equilibrium constant measurements are carried out in

three quite distinct experimental systems operating at rather

different pressures. These are the high pressure ion source coupled to a mass spectrometer (MS), the flowing

afterglow tube (FAG) whose equilibrium ion composition is

sampled by a quadrupole mass spectrometer , and ions trapped

for finite time in a cyclotron field (ICR) with subsequent

ejection and analysis by rf absorption. These techniques

have been discussed in detail in a number of reviews (2-6).

2.3 Bracketing measurements

The same techniques described immediately above can be

used to examine the occurrence or non-occurrence of a proton

transfer reaction, and applying the criterion that occurrence

implies a negative free energy change and non-occurrence

implies a positive free energy change. Accepting these

assumptions, one could in principle bracket the range which

the gas phase basicity of a molecule lies (7). Using

different reagent ions many authors have reported such

relative basicities as relative "proton affinities". Results

x
obtained from this approach should be used only with great

caution; it is now well known that many endoergic reactions

may occur with a rate constant high enough that they can easily be observed under the experimental conditions

described above (3). Furthermore, many proton transfer

reactions which are clearly exothermic are not observed to occur if more favorable reaction channels exist (8).

2.4 Calculations and estimates

In principle, proton affinities or ion heats of formation

can be calculated quantum mechan i cal ly . We include here only

the very high quality calculations carried out on H3 + (see

Tables). Another type of calculation deals with the

evaluation of the lattice energy of an ionic crystal (CLE)

(9). For an ammonium halide, for example, this gives the

energy of the crystal relative to the gas phase ammonium and

halide ions. These can then be related to gas phase neutral

species via a Born-Haber cycle, and will yield the proton

affinity of NH3(gas). Lastly, there are a number of

empirical correlations of proton affinities with other

physical parameters such as core ionization potentials (10).

2.5 References

1. H. M. Rosenstock, "The Measurement of Ionization and

Appearance Potentials," Int. J. Mass Spectrom. Ion Phys.

20, 139 ( 1976 ) .

2. S. G. Lias, "Thermodynamic Information from Ion-Molecule

Equilibrium Constant Determinations," in "Ion Cyclotron

Resonance Spect romet ry" (H. Hartmann and K.-P. Wanczek,

eds.). Springer- Verlag, Berlin (1978).

xi
3. S. Lias, "Thermochemi stry of Polyatomic Cations," in

"Kinetics of Ion Molecule Reactions," (P. Ausloos, Ed.),

Plenum Press, New York (1979), pg. 233.

4. P. Kebarle, "Ion Thermochemistry and Solvation from Gas

Phase Ion Equilibria," Ann. Rev. Phys. Chem. 28, 445

( 1977) .

5. D. H. Aue and M. T. Bowers, "Stabilities of Positive Ions

from Equilibrium Gas Phase Basicity Measurements," in "Gas

Phase Ion Chemistry," (M. T. Bowers, ed.). Academic Press,

New York ( 1979)

.

6. D. K. 3ohme, "The Kinetics and Energetics of Proton

Transfer," in "Interactions between Ions and Molecules," (P.

Ausloos, ed.). Plenum Press, New York (1975).

7. J. Long and B. Munson, "Proton Affinities of some Oxygenated Compounds," J. Am. Chem. Soc. 95, 2427 (1973).

8. P. Ausloos and S. G. Lias, "Proton Affinity of

Di chlorocarbene, " J. Am. Chem. Soc. 100, 4594 (1978).

9. J. Sherman, "Crystal Energies of Ionic Compounds and

Thermochemical Applications," Chem. Rev. 11, 93 (1932).

10. J. A. Jen and T. D. Thomas, "Core Ionization Potentials

in Dimethyl Ethor and Methylami ne , " J. Electron Spectrosc.

4, 43 (1974).

xii
3. ORGANIZATION OF THE INFORMATION

3.1 A -typical measurement entry is shown below:

C8H10 CAS REGN : 108-38 -3

C

•o

•o

C**C cxxc V

Benzene, 1,3-dimethyl- (9CI)

m-Xylene (8CI)

GB (exp) 182+/-3 kcal/mol T emperature : 340 K

PA (exp) : 189.7+/-3 kcal/mol T emperature : 340 K

Chong, S. 1., and Franklin, J. L.,

Proton Affinities of Benzene, Toluene, and

J. Am. Chem. Soc. 94, 6630 (1972).

the Xylenes,

Method used : MS

Equilibrium relative to CH3SH

Entropy change assumed zero and ( CH3 ) 20

G3 (exp) • 187.2+/-2 kcal/mol T emperatu re : 298 K

PA (exp) : 194.6+/-2 kcal/mol T emperature : 298 K

Devlin, J. L., Ill, Wolf, J. F., Taft, R. W., and

Hehre , W . J .

,

The Proton Affinities of Toluene,

J. Am. Chem. Soc. 98, 1990 (1976).

Method used : ICR

Calculated entropy

Equilibrium relative to C6H6 (Benzene)
The entry gives successively the following information!

a) The empirical formula in Hill System order.

b) The Chemical Abstracts Service (CAS) Registry

Number

.

c) The structural formula (see discussion below).

d) The Chemical Abstracts Service (CAS) Name, as given in the 8th Collective Index (8CI) and the

9th Collective Index (9CI). If it is the same in

both it is denoted with (8CI9CI).

e) The gas phase basicity, GB, in kcal/mol.

f) The proton affinity, PA, in kcal/mol.

g) The temperature at which the measurement was carried out

.

h) The literature citation.

i) The method used (see discussion below).

j) Additional comments on the nature of the

measurement

.

Where there are several measurements on the same species, the

numerical value, literature reference, method and associated

comments are listed successively.

The structural diagrams used in this publication have

been generated from connection tables by the Structure and

Nomenclature Search System (SANSS), one of the components of

the CIS. The following symbols have been used to represent

the different types of chemical bonds!

single bond

double bond

triple bond

ring alternating bond (e.g.» benzene)

tautomeric bond (e.g.» OZXCXXO in

carboxylic acids)

Hydrogen atoms are not explicitly included in the diagrams

but are understood to occupy any otherwise available bonds.

Tautomeric structures are recognized as equivalent and

the percent sign used in the structural diagrams under the

following conditions.

M = Q-ZH = HM-Q=Z = H fmQXXZ

xiv
when • a) . Q = C, N, S, P, Sb, As, Se, Te, Br, Cl, or I with any allowed

valence for the individual elements.

b) . M and Z = any combination of trivalent N and/or bivalent 0,

S , Se or Te atoms

c) . The bonds which are involved in the tautomer i zat i on may be in an acyclic chain, a ring system, or partly in each.

d) . The end points, M and Z, may be in adjacent rings of a fused

ring system. However, a nitrogen atom at a fusion point in a fused ring system can not be involved in tautomer i zat i on

e) . A deuterium or tritium may replace the migrating hydrogen

atom

f) . If more than one of the systems described above are linked

through a common atom, the hydrogen may be free to migrate

along the chain defining a larger tautomeric system.

The experimental methods were discussed in the preceding

section. They are abbreviated as follows:

CLE

El

EM

FAG

FIICR

MS

PI

TC

Crystal lattice energy

Threshold measurement by non-monoenerget i c electron

i mpact

Threshold measurement by monoenerget i c electron

i mpact

Flowing afterglow

Field ionization threshold

Ion cyclotron resonance

High pressure mass spectrometry

Threshold measurement by pho to i on i zat i on Theoretical calculation

Following the table of measurements in molecular formula

order. Section A, there are a number of indexes:

a) . The gas phase basicity index in which the file is ordered in

increasing order of gas phase basicity, with numerical values

arbitrarily given to four significant figures for purposes

of ordering. The page number refers to the main body of

information, Section A.

b) . The proton affinity index, structured in the same fashion.

c,d,e). Additional indices are provided for molecular formula, CAS

Registry Number and compound name. The compound name index

includes a number of synonyms in addition to the names adopted in the 8th and 9th collective indices.

xv

1

A r | CAS REGN : 7440-37-1

AR

Argon C8CI9CI)

PA (exp) <100.+/-. 5 kcal/mol Temperature •

Roche, A. E., Sutton, M. M., Bohme, D. K., and

Schiff, H. I.,

Determination of Proton Affinity from the Kinetics of Proton

Transfer Reactions. I. Relative Proton Affinities,

J. Chem. Phys. 55, 5480 (1971).

Method used ’ FAG

Bracketing relative to 02.
2

A sH3 | CAS REGN : 7784-42-1

AS

Arsine (8CI9CI)

GB (exp) ’ 172.3+/-2 kcal/mol Temperature : 300 K

PA (exp) : 180.9+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.»

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 54 1 7 ( 1 977 ).

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on NH3
3

I BF2H

1 CAS REGN : 13709-83-6

1 1 F**B** F

Borane, di.fluoro- (8CI9CI)

PA (exp) : 115+/-14 kcal/mol Temperature : 85 K

Pierce, R. C., and Porter, R. Ion-Molecule Chemistry of BF3

Inorg. Chem. 14, 1087 (1975).

F. , and HBF2 in Hydrogen

,

Method used • MS

Bracketing relative to CH4 and H2.
4

BF3 CAS REGN v 7637-07-2

F**B**F

*

F

Borane, trifluoro- (9CI)

Boron fluoride ( BF3 ) (8CI)

PA (exp) • 115+/-14 kcal/mol Temperature : 85 K

Pierce, R. C., and Porter, R. Ion-Molecule Chemistry of BF3

Inorg. Chem. 14, 1087 ( 1975).

F. , and HBF2 in Hydrogen,

Method used J MS

Bracketing relative to CH4 and H2.
5

B2H6 | CAS REGN : 19287-45-7

H**B

* x * X B**H

Diborane(6) (8CI9CI) i

!

I l

1 l i

1 PA (exp) : 147+/-4 kcal/mol | Temperature ' 79-86 K

1

1 Pierce, R. C., and Porter, R. F.,

Low-Temperature Chemical Ionization Mass Spectrometry

of Boron Hydrides. The Proton Affinities of Diborane

and TetraboraneC 1 0 )

,

J. Am. Chem. Soc. 95, 3849 (1973).

Method used : MS

Observed reaction C2H9+ + B2H6->2CH4 + B2H7 1

.

Reaction B2H7+ ->B2H5+ + H2 has delta

H formation = 3.0+/-. 3.

Based on delta H f o rmat i on ( B2H5 + ) = 232.
6

B3H5N3 | CAS REGN : Hot available

B**N

x x

x x N B

x x

x x B**N

. beta . -Borazi nyl radical

PA (exp) : 193+/-2 kcal/mol Temperature ’•

DeStefano, A. J., and Porter, R. F. Ion-Molecule Reactions of Cyclic Borazine Cations.

Thermodynamic and Kinetic Considerations,

J. Phys. Chem. SO, 2818 (1976).

Method used : MS

Bracketing relative to HC02C2H5 and (CH3)2C0. The

reactant ions are generated by photon impact
7

B3H6N3 | CAS REGN : 6569-51-3

B**N

x x

X x N B x x

x x B**N

Borazine C8CI9CI)

PA (exp) : 199+/-A kcal/mol Temperature :

Betowski, L. D., Solmon, J. J., and Porter, R. F.,

The Proton Affinity of Borazine,

Inorg. Chem. 11, A2A (1972).

Method used : MS

Bracketing relative to CAH6(2--Butyne) and NH3
8

B4H8

1 CAS REGN : 12007-71-5

1 B***B

X X

X X B#*XB

T etraborane(8

)

PA (exp) • 187+/-7 kcal/mol Temperature • 375 K

Solmon, J. J., and Porter, R. F. , Chemical Ionization Mass Spectrometry of Selected

Boron Hydr i des

,

J. Am. Chem. Soc. 94, 1443 (1972).

Method used ’ MS

Bracketing relative to C3D6 and (CH3)2C0.
9

BAH 10

1 1

| CAS REGN : 18283-93-7

1 1

| H***XXB*****H

X XX X XX XX

BxxxxxB

XX XX

X XX X

| h*xxxxb*****H

Tetraborane( 10) (8CI9CI)

PA (exp) : 144+/-5 kcal/mol Temperature : 140-300 K

Pierce, R. C., and Porter, R. F.,

Low-Temperature Chemical Ionization Mass Spectrometry

of Boron Hydrides. The Proton Affinities of Diborane

and Tetraborane( 1 0 ) , J. Am. Chem. Soc. 95, 3849 (1973).

Method used MS

Based on delta H f ormat i on( B2H5+ ) and estimating delta S. Equilibrium of B2H5+ + B2H6 -> B4H11+.
10

B5H9 CAS REGN : 19624-22-7

Hxxxxxb*xxxxh

X XXX X

X X X X X BxxB*#B

X X X X X

X XXX X Hxxxxxb***xxh

PentaboraneC 9 ) (8CI9CI)

PA (exp) : 172+/-2 kcal/mol Temperature : 373~3 K

Solmon, J. J., and Porter, R. F.,

Chemical Ionization Mass Spectrometry of Selected

Boron Hydrides,

J. Am. Chem. Soc. 94, 1443 (1972).

Method used • MS

Based PA (H20) = 170.3.

Bracketing relative to H20 and H2S.
1

I BrH

1 CAS REGN : 10035-10-6

I BR

| Hydrobromic acid (8CI9CI)

I PA (exp) : 141+/-3 kcal/mol Temperature •

Haney, M. A., and Franklin, J L . , Mass Spectrometri c Determination of the Proton

Affinities of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used : MS

Absolute PA value estimated by assuming that for

reaction RH+ + RH -> RH2+ + R; the delta H ~5X TC.

TC = measured translational energy of the products.
12

CBrN

• CAS REGN : 506-68-3'

. .. N##C**BR

Cyanogen bromide (8CI9CI)

PA (exp) • 179+/-3 kcal/mol Temperature • 300 K

Staley, R. H., Kleckner, J. E , and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used : ICR

Calculated entropy

Equilibrium relative to AsH3, HC02H and F2CHCH20H
13

1

I CC1N

1 . J

CAS REGN : 506-77-4

| N#8C**CL

I Cyanogen chloride (8CI9CI)

PA (exp) • 177+/-3 kcal/mol Temperature : 300 K

Staley, R. H., Kleckner, J. E , and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used : ICR

Equilibrium relative to F2CH2CH , OH and HCHO

GB (exp) • 169.6+/-2 kcal/mol Temperature : 300 K

PA (exp) : 177.4+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
CC12 CAS REGN : 1605-72-7

CL*C**CL

Methylene, dichloro- (8CI9CI)

PA (exp) : 194.7+/-4 kcal/mol Temperature • 325 K

Ausloos, P., and Lias, S. G. The Pro-ton Affinity of Di chlorocarbene.

To be published in J. Am. Chem. Soc.

Method used : ICR

Bracketing relative to Me20 and Et20; scale based

on PA ( NH3 ) = 202.8

PA (exp) ’ 200.4+/-1.5 kcal/mol Temperature ' 300 K

Lias, S. G., and Ausloos, P. Reactions of CC12H+ and CF2H+ with Organic and

Inorganic Compounds: Proton Affinities and Heats of

Formation of CC12 and CF2,

Intern. J. Mass Spectrom. Ion Phys. 22, 135 (1976).

Method used : ICR

Bracketing relative to NH3 and (CH3)2S

Continued on next page
15

GB not calculated for this reference

PA (exp) 208.3+/-2 kcal/mol Temperature : 300 K

Levi, B. A., Taft, R. W., and Hehre, W. J Di chlorcarbene,

J. Am. Chem. Soc. 99, 8454 (1977).

Method used : ICR

Calculated entropy

Bracketing relative to CF3CH2CH2NH2 and C6H5NH2;

scale based on NH3

PA (exp) : 209+/-2 kcal/mol Temperature : 300 K

Levi, B. A., Taft, R. W., and Hehre, W. J.

Di chlorocarbene,

J. Am. Chem. Soc. 99, 8454 (1977).

Method used : ICR

Calculated entropy

The deuterium affinity determined by bracketing

techniques relative to 2-CF3 Pyridine and

CF3 ( CH2 ) 2NH2 ; scale based on NH3
16

I CF2 | CAS REGN : 2154-59-8

F**C** F

Methylene, difluoro- C8CI9CI)

PA (exp) : 178.5+/-1 kcal/mol T emperature 300 K

Lias, S. G., and Ausloos, P. Reactions of CC12H+ and CF2H+ with Organic and

Inorganic Compounds: Proton Affinities and Heats of

Formation of CC12 and CF2,

Intern. J. Mass Spectrom. Ion Phys. 22, 135 (1976).

Method used : ICR

Bracketing relative to H2S and HCOOH and also

observing the following: CD5+ + CF2HCL ->

CD4 + DC1 + CF2H+ and CD5+ + CF3H -> CD<+ + DF + CF2H+. Scale based on PA (H20) = 170.1 kcal/mol
17

CF4 | CAS REGN : 75-73-0

FXX F*XC**F

x

XF

Methane, tetrafluoro- (9CI)

Carbon tetraf luor i de (SCI)

PA (exp) • 121+/-4 kcal/mol T emperature 30 0 K

Roche, A. E., Sutton, M. M. Bohme , D . K . , and

Schiff, H. I.,

Determ i nat i on of Proton Affinity from the Kinetics of

Proton Transfer Reactions. I. Relative Proton Affinities,

J. Chem. Phys. 55, 5430 (1971).

Method used = FAG

Bracketing relative to CH4 and N2

PA (exp) ' 121+/-5 kcal/mol Temperature • 298 K

Blint, R. J., McMahon, T. B., and Beauchamp, J. L.,

Gas-Phase Ion Chemistry of Fluoromethanes by Ion

Cyclotron Resonance Spectroscopy. New Techniques

for the Determination of Carbonium Ion Stabilities,

J. Am. Chem. Soc. 96, 1269 (1974).

Method used : ICR

Bracketing relative to CH4. Using IP of H and CF4 and

also HA of CF4+.
18

1

I CHF3

1

I CAS REGN : 75-46-7

1 F**C**F

X

X

F

I Methane, trifluoro- (8CI9CI)

PA (exp) : 147+/-5 kcal/mol Temperature : 298 K

Blint, R. J., McMahon, T. B., and Beauchamp, J. L.,

Gas-Phase Ion Chemistry of Fluoromethanes by Ion

Cyclotron Resonance Spectroscopy. New Techniques

for the Determination of Carbonium Ion Stabilities,

J. Am. Chem. Soc. 96, 1269 (1974).

Method used ’ ICR

Bracketing relative to CH3F. Using IP of H and CH3F,

also HA (CH3F+).
1

I CHN

1 r

CAS REGN : 74-90-8

| CSSN

Hydrocyanic acid (8CI9CI)

GB (exp) : 166.9+/-2 keal/mol Temperature : 300 K

i PA (exp) ' 174.5+/-2 keal/mol Temperature : 300 K

Freeman, C. G., Harland, P. W., and McEwan, M. J. The Equilibrium H3S+ + HCN = H2CN + + H2S and the

Relative Proton Affinities of HCN and H2S,

Intern. J. Mass Spectrom. Ion Phys. 27, 77 (1978).

Method used : FAG

Equilibrium relative to H2S; scale based on NH3

PA (exp) : 139 keal/mol Temperature •

Haney, M. A., and Franklin, J. L.,

Mass Spectrometr i c Determination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used = MS

Estimated delta H = 5X translational

energy of the product of reaction

RH+ + RH -> RH2+ + R Continued on next page
20

GB ( exp

)

166 . 7+/-2 kcal/mol Temperature 300 K

PA ( exp

)

174.5+/-2 k ca 1/mo 1 T emperature 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., ancj Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

| CH2F2 CAS REGN : 75-10-5

1

j F**C**F

1 Methane, difluoro- (8CI9CI)

I PA (exp) - 147+/-5 kcal/mol Temperature • 298 K

Blint, R. J., McMahon, T. B., and Beauchamp, J. L.,

Gas-Phase Ion Chemistry of Fluoromethanes by Ion

Cyclotron Resonance Spectroscopy. New Techniques

for the Determ i nat i on of Carbonium Ion Stabilities,

J. Am. Chem. Soc. 96, 1269 (1974).

Method used • ICR

Bracketing relative to CH3F and CO

and CH2F2 , also HA (CH2F2+).

Using IP of H
CH2N2 CAS REGN : 33A-88-3

N++N++C

Methane

,

diazo- (8CI9CI)

PA (exp) • 207+/-5 kcal/mol Temperature : 300 K

Foster, M. S., and Beauchamp, J. L.,

Gas-Phase Ion Chemistry of Azornethane by Ion

Cyclotron Resonance,

J. Am. Chem. Soc. 9A, 2A25 (1972).

Method used • ICR

Bracketing relative to NH3 and CH3NH2

| CH20

1 CAS REGN : 50-00-0

C + + 0

| Formaldehyde (8CI9CI)

1 PA (exp) : 162+/-3 kcal/mol Temperature :

Harrison, A. G., Ivko, A., and Van Raalte, D.,

Energetics of Formation of Some Oxygenated Ions

and the Proton Affinities of Carbonyl Compounds,

Can. J. Chem. A A , 1625 (1966).

Method used • El

Electron impact fragmentation (various molecules).

Conti nued on next page
22

PA (exp) : 169+/-1 kcal/mol Temperature • 298 K

Refaey, K. M. A., and Chupka, W. A.,

Photo i on i zat i on of the Lower Aliphatic Alcohols

with Mass Analysis,

J. Chem. Phys. 48, 5205 (1968).

Method used ; PI

Appearance potential by IP fragmentation of CH30H

PA (exp) : 170 kcal/mol Temperature :

Lossi ng, F. P

.

Heats of Formation of Some Isomeric [CnH2n + 10]+

Ions. Substitutional Effects on Ion Stability,

J. Am. Chem. Soc. 99, 7526 (1977).

Method used •" EM

Electron impact fragmentation (various molecules)

using EM. delta Hf(H+) = 365.7

GB (exp) ’ 167.2+/-2 kcal/mol Temperature ’• 300 K

PA (exp) ’ 174.6+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
23

1

I CH202

1 CAS REGN : 64-18-6

1 oy.y.cxxo

| Formic acid (8CI9CI)

1 PA (exp) • 178+/-4 kcal/mol Temperature • 323-373 K

Long, J., and Munson, B.,

Pro-ton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to CH30H and H2S

PA (exp) : 186.8 kcal/mol Temperature :

Goldenfeld, I. V., Ko r o sty shev sky , I. Z., and

Mischanchuk, B. G.,

Analysis of Field Ion Energies in a Mass Spectrometer

,

Int. J. Mass Spectrom. Ion Phys. 13, 297 (1974).

Method used • FI PA derived from field appearance potential. Correction

for neutral particles potential energy

Continued on next page
24

PA (exp) • 179+/-3 kcal/mol Temperature ’• 340 K

Chong, S. L., and Franklin, J L. , Heats of Formation of Protonated Cyclopropane,

Methylcyclopropane, and Ethane,

J. Am. Chem. Soc. 94, 5347 (1972).

Method used : MS

Correction for path degeneracy.

Equilibrium; scale based on CH3CH=CH2.

GB (exp) : 162.5+/-2 kcal/mol Temperature ’• 600 K

PA (exp) : 178.9+/-2 kcal/mol Temperature • 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ; MS

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
25

GB (exp) : 171. 9+/-2 kcal/mol Temperature : 300 K

PA ( exp )

: 180. 1+/-2 kcal/mol Temperature : 300 K

Wolf, J Mcl ver

,

. F. , R. T Staley, R. H., Koppel, I., Taagepera, M.,

, Jr., Beauchamp, J. L., and Taft, R. W.»

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

I CH3Br

1 CAS REGN : 74-83-9

I BR*C

I Methane, bromo- (8CI9CI)

I PA (exp) : 163 kcal/mol Temperature ' 300 K

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt, S. L.,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy

,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used : ICR

Bracketing and using also IP's of H and CH3Br

and HA ( CH3BR+ ) .
CH3C1 CAS RE6N : 74-87-3

: C**CL

Methane, chloro- (8CI9CI)

PA (exp) : <170.3 kcal/mol Temperature :

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,.

J. Am. Chem. Soc. 95, 2427 (1973).

Method used : MS

Bracketing relative to H20.

PA (exp) : 164+/-3 kcal/mol Temperature •

Haney, M. A., and Franklin, J. L.,

Mass Spectrometr i c Determination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used '• MS

Absolute PA value estimated by assuming

that for reaction RHt + RH ->R + RH2+ the

delta H ~5X TC.

TC = measured translational energy of the products

Continued on next page
27

PA (exp) : “160 kcal/mol Temperature 300 K

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt , S. L.,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used : ICR

Bracketing and using also IP’s of H and CH3CL

and HACCH3CL+)

.

T

I CH3F

1 CAS REGH : 593-53-3

| C**F

| Methane, fluoro- (8CI9CI)

I PA (exp) • 151+/-5 kcal/mol Temperature ' 298 K

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt, S. L.,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy

,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used ' ICR

Using also the IP’s of H and CH3F and HA of CH3F+.
28

CH3I CAS REGN : 74-88-4

C**I

Methane, iodo- (8CI9CI)

PA Cexp) : 174+/-3 kcal/mol Temperature • 300 K j

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt, S. L.,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy,

J. Am. Chem. Soc. 94, 2798 C 1972) .

Method used : ICR

Bracketing and using also

and HA(CH3I+).

IP's of H and CH3I
29

I CH3N02

1 CAS REGN : 75-52-5

| 0++N**C

+

+

0

I Methane, nitro- (8CI9CI)

I PA (exp) ' ~182 kcal/mol Temperature • 300 K

McAllister, T., and Pitman, P. Ion-Molecule Reactions and Proton Affinities of Methyl

Nitrite and N i tromethane

,

Intern. J. Mass Spectrom. Ion Phys. 19, 241 (1976).

Method used • ICR

Bracketing relative to CH30H and (CH3)2C0

PA (exp) : 182+/-2 kcal/mol Temperature : 300 K

Kriemler, P., and Buttrill, S. E., Jr.,

Ion-Molecule Reactions and the Proton Affinities

of the N i troalkanes . I. Nitro methane and nitroethane,

J. Am. Chem. Soc. 95, 1365 (1973).

Method used : ICR

Bracketing relative to CH30H.
30

CH3N02 CAS REGN : 624-91-9

0++N**0**C

Nitrous acid, methyl ester (8CI9CI) .

PA (exp) : 190.3+/-3 kcal/mol Temperature : 300 K

McAllister, T., and Pitman, P. Ion-Molecule Reactions and Proton Affinities

Nitrite and Ni tromethane.

Intern. J. Mass Spectrom. Ion Phys. 19, 241

of Methyl

( 1976 ) .

Method used : ICR

Bracketing relative to C2H50H and ( CH3 ) 2C0

CH4

r

CAS REGN : 74 i 00 (M 1 00

C

Methane (8CI9CI)

PA (exp) : 127+/-2 kcal/mol Temperature : 78,300 K

Chupka, W. A., and Berkowitz, J. , Photo i on i zat i on of Methane: Ionization Potential and

Proton Affinity of CH4,

J. Chem. Phys. 54, 4256 (1971).

Method used : PI

From PI~ef f i ci ency curve of CH5+ in CH4.

Continued on next page
PA (exp) • 126+/-1 kcal/mol Temperature = 483+/-10 K

Munson, M. S. B., and Field, :

. H. , Reactions of Gaseous Ions. XV. Methane + 1/S Ethane

and Methane + 1% Propane,

J. Am. Chem. Soc. 87, 3294 (1965).

Method used : MS

Observed reactions: CH4+ + CH4 -> CH5+ + CH3,

CH5+ + C2H6 -> C2H5+ + H2 + CH4

.

PA (exp) 131.4 kcal/mol T emperature 298 K

Schiff, H. I., and Bohme, D. K.,

Flowing Afterglow Studies at York University,

Int. J. Mass Spectrom. Ion Phys. 16, 167 (1975)

Method used • FAG

Equilibrium relative to N20, delta S estimated. Based on PA (N20) which is derived

from calculated PA (CO).

PA (exp) : 130.5 kcal/mol Temperature : 340 K

Kasper, S. F., and Franklin, J. L.,

Ion-Molecule Reactions in the System C02-CH4,

J. Chem. Phys. 56, 1156 (1972).

Method used : MS

Entropy change assumed zero Equilibrium relative to C02; found delta

G = -1.35 Kcal/mol. Based on C02 with PA = 129.1.

(Int. J. Mass Spectrom. Ion Phys. 16, 167 (1975)).
32

CH40 CAS REGN : 67-56-1

C**0

Methanol C8CI9CI)

1

PA (exp) ’ 182+/-3 kcal/mol Temperature ’•

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to CH3CH0 and HCOOH

.

PA (exp) : 179.0+/-2 kcal/mol Temperature : 299-329 K

Wei, L. Y. , and Bone, L. I.,

Ion-Molecule Reactions in Methanol and Hydrogen Sulfide,

J. Phys. Chem. 78, 2527 (1974).

Method used ’ MS

Equilibrium relative to H2S

Van't Hoff plot

Continued on next page
33

PA (exp) • 182 kcal/mol Temperature •

Haney, M. A., and Franklin, J L. , Mass Spectrometric Do-termination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4323 (1969).

Method used : MS

Delta H estimated = 5X total translational

energy of the products of RH+ + RH -> RH2 + + R

GB (exp) : 166.5+/-2 kcal/mol Temperature : 600 K

PA (exp) • 182.1+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Mea su remen 1 5

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used = MS

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
34

GB (exp) ; 174.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 182.2+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

I CH4S | CAS REGN : 74-93-1

C**S

Methanethi ol (8CI9CI)

GB (exp) : 177.5+/-2 kcal/mol Temperature • 300 K

PA (exp) " 185.3+/-2 kcal/mol Temperature : 300 K

Harrison, A. G., Lin, P. H., and Tsang, C. W.,

Pro-ton Transfer Reactions by Trapped-Ion Mass

Spectrometry,

Int. J. Hass Spectrom. Ion Phys. 19, 23 (1976).

Method used : MS

Equilibrium; scale based on CH3CH0

Entropy change assumed zero Continued on next page
35

PA (exp) 1 9 9+/- 1 0 kcal/mol Temperature :

Hobrock, B. G. and Kiser, R. W.,

Electron Impact Investigations of Sulfur Compounds.

II. 3-Methyl-2-Thi abutane , 4 -Th i a- 1 -Pentene , and

3,4-Dithiahexane,

J. Phys. Chem. 67, 648 (1963).

Method used • El

Appearance potential by electron impact of sulfur

compounds

.

GB (exp) ‘ 178.1+/-2 kcal/mol Temperature 300 K

PA (exp) : 185.9+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
36

CH5N

C**N

Methanamine C9CI)

Methylamine (8CI)

GB (exp) : 202.9+/-2 kcal/mol Temperature • 300 K

PA (exp) ’ 211.3+/-2 kcal/mol Temperature ' 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used s ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 211 kcal/mol Temperature :

Haney, M. A., and Franklin, J. L . , Mass Spectrometr i c Determination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used s MS

Estimated delta H = 5X translational energy of

the product of reaction RH+ + RH -> RH2+ + R

| CAS REGN : 74-89-5

Continued on next page
37

GB (exp) • 205.7+/-3 kcal/mol Temperature : 298 K

PA (exp) • 213.7+/-3 kcal/mol Temperature • 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ‘ ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 195.9+/-2 kcal/mol Temperature • 600 K

PA (exp) : 213.1+/-2 kcal/mol Temperature : 600 K

Brigqs, J. P., Yamdagni, R., and Kebarle, P.,

Intrinsic Basicities of Ammonia, Methylami nes. Anilines, and Pyridine from Gas-Phase ProtonExchange Equilibria,

J. Am. Chem. Soc. 94, 5128 (1972).

Method used • MS

Equilibrium; scale based on NH3

Entropy change assumed zero
38

CH5P CAS REGN s 593-54-4

c**p

Phosphine, methyl- (8CI9CI)

GB (exp) • 193.4+/-2 kcal/mol Temperature : 300 K

PA (exp) s 201.8+/-2 kcal/mol Temperature : 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
39

j CO

r

CAS REGN : 630-08-0

:

1 c##o

1 Carbon monoxide (8CI9CI)

I PA (exp) : 143+/-2 kcal/mol Temperature •

Matthews, C. S., and Warneck, P. , Heats of Formation of CH0+ and C3H3+ by Photo i on i zat i on

,

• J . Chem . Phy s . 51, 854 (1969)

| Method used : PI

Appearance potential by photo i on i zat i on . PA value derived from

delta H f ormat i on ( HC0+ )

.

PA (exp) 142.7+/-3 kcal/mol Temperature •

Haney, M. A., and Franklin, J L. , Excess Energies in Mass Spectra of some OxygenContaining Organic Compounds,

Trans. Faraday Soc. 65, 1794 (1969).

Method used : MS

Appearance potential by electron impact from HCOOH, CH3CH0

and C2H3CH0. Correction for excess energy.
- 40 -

C02 CAS REGN : 124-38-9

0++C++0

Carbon dioxide (8CI9CI)

PA (exp) : 130.7+/-1 kcal/mol Temperature •

Warneck, P. Heat of Formation of the HCO Radical,

Z. Naturforsch. 29, 350 (1974).

Method used : PI

Appearance potential by photo i on i zat i on

.

= 365.7

delta Hf(H+)

PA (exp) : 129.1 kcal/mol Temperature • 298 K

Schiff, H. I., and Bohme, D. K.,

Flowing Afterglow Studies at York University,

Int. J. Mass Spectrom. Ion Phys. 16, 167 (1975)

Method used • FAG

Calculated entropy.

Equilibrium; scale based on CO VALUE

Continued on next page
PA (exp) 124+/-2 kcal/mol T emperature 30 0 K

Moot-Ner (Mautner) , M., and Field, F. Proton Affinities and Cluster Ion Stabilities in

C02 and CS2. Applications in Martian Ionspheric

Chemi stry

,

J. Chem. Phys. 66, 4527 (1977),

Method used • MS

Van't Hoff plot

Equilibrium; scale based on PA (CH4) = 126.8

GB (exp) ‘ 123+/-3 kcal/mol Temperature : 300 K

PA (exp) : 124+/-3 kcal/mol Temperature : 300 K

Meot-Ner (Mautner), M., and Field, F. H. Proton Affinities and Cluster Ion Stabilities in

C02 and CS2. Application in Martian Ionspheric

Cham i stry

,

J. Chem. Phys. 66, 4527 (1977).

Method used •* MS

Calculated entropy

The measurements done in the temperature range of

400-650K. Using the Hoff plot the delta H and delta S at

300K were derived. Using PA (CH4)-126.8

Continued on next page
PA (exp) J 123+/-3 kcal/mol Temperature : 800 K

Fehsenfeld, F. C., Lindinger, W., Schiff, H. I.,

Hemsworth, R. S., and Bohne, D. K. Determination of the Proton Affinity from the

Kinetics of Proton Transfer Reactions. VI. The

Relative Proton Affinities of M2, Xe, and C02,

J. Chem. Phys. 64, 4887 (1976).

Method used s FAG

Van't Hoff plot

Equilibrium relative to N2 and Xe; scale based on

PA (N2) = 112.6

Van't Hoff plot

CS2 CAS REGN : 75-15-0

5++C++S

Carbon disulfide (8CI9CI)

GB (exp) s 165.7+/-2.5 kcal/mol Temperature • 300 K

PA (exp) • 168+/-2.5 kcal/mol Temperature : 300 K

Meot-Ner (Mautner), M., and Field, F. H. Proton Affinities and Cluster Ion Stabilities in

C02 and CS2. Applications in Martian Ionspheric

Chemi stry

,

J. Chem. Phys. 66, 4527 (1977).

Method used • MS

Calculated entropy

The measurements done in the temperature range

of 400-650K. Using the Hoff plot the delta H and delta S at 300K were derived. Equilibrium, scale based on NH3
C2C13N

CL

XX CL*C**C##N

x

xCL

1

| CAS REGN : 545-06-2

j Acetonitrile, trichloro- (8CI9CI)

GB (exp) : 169.7+/-2 kcal/mol T emperature 300 K

i PA (exp) : 177.5+/-2 kcal/mol T emperature 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W. , Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C2D60 CAS REGN : 17222-37-6

c*#o**c

Methane-d3, oxybis- (9CI)

(Methyl ether)-d6 (8CI)

GB (exp) : "186 kcal/mol Temperature : 374 K

Blair, A. S., and Harrison, A. G.,

Bimolecular Reactions of Trapped Ions. V. Ionic

Chemistry of Simple Oxygen-containing Molecules,

Can. J. Chem. 51, 703 (1972).

Method used • MS

Equilibrium relative to CH3CH0.

Found delta G "3.
45

1

I C2HF3

1

1 CAS REGN : 359- 1 1-5

1 F*kc++C**F

xx

F

| E t h e n e , -trifluoro- (9CI)

1 Ethylene, trifluoro- (8CI)

PA (exp) ' 172+/-2 keal/mol Temperature • 300 K

' R i dge , D . P .

,

Gas Phase Proton Affinities of Several Fluoroethylenes,

J. Am. Chem. Soc. 97, 5670 (1975).

Method used • ICR

Bracketing relative to H20 and H2S.
46

C2HF302 | CAS REGN : 76-05-1

Fx

x Fxxc**CXXO

x %

F 0

Acetic acid, trifluoro- (8CI9CI)

PA (exp) ' 172+/-2 kcal/mol Temperature : 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used - MS

Bracketing relative to H2S and H20

GB (exp) : 154.7+/-2 kcal/mol Temperature : 600 K

PA (exp) : 171.9+/-2 kcal/mol Temperature • 600 K

Yamdagni , R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Equilibrium; scale based on NH3

Entropy change assumed zero Continued on next page
47

GB (exp) : 165.1+/-2 kcal/mol Temperature : 300 K

PA (exp) • 173.3+/-2 kcal/mol Temperature '• 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

I C2H2C1N

1 CAS REGN : 107-14-2

I CL*C**C##N

| Acetonitrile, chloro- (8CI9CI)

1 GB (exp) : 173.1+/-2 kcal/mol Temperature : 300 K

I PA (exp) : 180.9+/-2 kcal/mol Temperature • 300 K

Wolf, J. F.» Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
48

C2H2F2 CAS REGN : 75-38-7

F**C++C

#

#F

Ethene, 1 , 1-di f luoro- (9CI)

Ethylene, 1 , 1-di f luoro- C8CI)

PA (exp) i 178+/-4 kcal/mol Temperature '• 300 K

' Ri dge, D . P .

,

Gas Phase Proton Affinities of several Fluoroethylenes,

J. Am. Chem. Soc. 97, 5670 (1975).

Method used • ICR

Bracketing relative to C2H5I and CH30H

PA (exp) • 174.8 kcal/mol Temperature ' 298 K

Williamson, A. D., LeBrenton, P . R . , and

Beauchamp, J . L .

,

Photoionization Mass Spectrometry of 2-Fluoropropane

and 2 , 2-Di f luoropropane . A Hovel Determination of the

Proton Affinity of Vinyl Fluoride and 1 , 1 — D i f luoroethylene,

J. Am. Chem. Soc. 98, 2705 (1976).

Method used ’ PI

Appearance potential by phtot i on i zat i on of (CH3)2CF2.
49

C2H2F2 CAS REGN : 1630-77-9

L

F**C++C**F

Ethene, 1 ,2-di f luoro-, (Z)- (9CI)

Ethylene, 1 , 2-di f luoro-, (Z)- (8CI)

PA (exp) • 166+/-4 kcal/mol Temperature J 300 K

R i dge > D . P . , Gas Phase Proton Affinities of several Fluoroethylenes,

J. Am. Chem. Soc. 97, 5670 (1975).

Method used * ICR

Bracketing relative to C2H5F and H20.

C2H2F2

r CAS REGN : 1630-78-0

L F**C++C**F

Ethene, 1,2-difluoro-, (E)~ (9CI)

Ethylene, 1,2-difluoro-, (E)- (8CI)

PA (exp) : 167+/-4 kcal/mol Temperature : 300 K

R i dge , D . P .

,

Gas Phase Proton Affinities of several Fluoroethylenes,

J. Am. Chem. Soc. 97, 5670 (1975).

Method used • ICR

Bracketing relative to C2H5F and H20.
C2H20 CAS REGN : ^63-51-4

0++C++C

Ethenone (9CI)

Ketene (8CI)

PA (exp) : 194.1+/-1 kcal/mol Temperature • 350 K

Ausloos, P., and Lias, S. G. The Proton Affinity of Ketene and the Heat of

Formation of CH3C0+,

Chem. Phys. Letters 51, 53 (1977).

Method used ICR

Equilibrium; scale based on PA (iso-C4H8) = 193.5+/-1

PA (exp) : 195i9+/-2 kcal/mol Temperature • 300 K

Vogt, J., Williamson, A. D., and Beauchamp, J. L. Properties and Reactions of Ketene in the Gas Phase

by Ion Cyclotron Resonance Spectroscopy and Photo i on i zat i on Mass Spectrometry . Proton Affinity, Site Specificity of

Protonation, and Heat of Formation of Ketene,

J. Am. Chem. Soc. 100, 3478 (1978).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
51

C2H3C1 02 CAS REGN : 79-1 1-8

0%/(C**C**CL

%

%

0

Acetic acid, chloro- (8CI9CI)

GB (exp) *• 166.8+/-2 kcal/rr.ol Temperature : 600 K

PA (exp) : 184+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Equilibrium; scale based on NH3

Entropy change assumed zero
52

C2H3C1 30 CAS REGN : 115-20-8

CL

*

x CL*C**C**Q

x

xCL

Ethanol, 2 , 2 ,

2

- tr i chloro- (8CI9CI)

GB (exp) ; 171.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 179+/-2 kcal/mol Temperature : 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
53

C2H3F

r

CAS REGN : 75-02-5

: F**C++C

Ethene, fluoro- (9CI)

Ethylene, fluoro- (8CI)

PA (exp) : 174+/-1 kcal/mol Temperature - 300 K

R i dge, D . P . , Gas Phase Proton Affinities of several Fluoroethylenes,

J. Am. Chem. Soc. 97, 5670 (1975).

Method used • ICR

Bracketing relative to H2S and CH20.

PA (exp) : 173.6 kcal/mol Temperature : 298 K

Williamson, A. D., LeBreton, P. R., and

Beauchamp , J . L .

,

Photo i on i zat i on Mass Spectrometry of 2-Fluoropropane and 2 , 2-D i f 1 uo r opr opane . A Novel

Determination of Vinyl Fluoride and 1 , 1-Di f louroethylene,

J. Am. Chem. Soc. 98, 2705 (1976).

Method used • PI

Appearance potential by photo i on i zat i on of (CH3)2CHF.
54

C2H3F02 CAS REGN : 144-49-0

0%%C*XC**F

X

%

0

Acetic acid, fluoro- (8CI9CI)

GB (exp) : 167.3+/-2 kcal/mol Temperature : 600 K

PA (exp) : 184.5+/-2 kcal/mol Temperature • 600 K

Yamdagni , R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used s MS

Equilibrium; scale based on NH3

Entropy change assumed zero
55

C2H3F30

r

CAS REGN : 75-89~8

F

*

* F**C**C**0

XX

F

Ethanol, 2 , 2 , 2~tr i f luoro- (8CI9CI)

GB (exp) : 164.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 172.2+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
56

C2H3N CAS REGN : 75-05-8

N##C**C

Acetonitrile (8CI9CI)

PA (exp) : 189. 5+/-4. 5 kcal/mol Temperature • 298 K

Gray, G. A .

,

Study of Ion-Molecule Reactions and Reaction

Mechanisms in Acetonitrile by Ion Cyclotron Resonance,

J. Am. Chem. Soc. 90, 6002 (1968).

Method used • ICR

Bracketing relative to CH3CH0 and ( CH3 ) 2C0

PA (exp) : 186+/-1 kcal/mol Temperature •

Haney, M. A., and Franklin, J. L.,

Mass Spectrometr i c Determination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used : MS

Translational energy of RH2+ has been

measured assuming delta H = 5X translational

energy for reaction RH+ + RH -> RH2 + + R Continued on next page
57

GB (exp) ’• 179.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 187+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 171.8+/-2 kcal/mol Temperature : 600 K

PA (exp) •' 187.4+/-2 kcal/mol Temperature '• 6 00 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3
58

C2H3NS CAS REGN : 556-61-6

S++C++N**C

Methane, i sothi ocyanato- (9CI)

I sothi ocyan i c acid, methyl ester (8CI)

PA (exp) : 189+/-6 kcal/mol Temperature •’ 300 K

McAl 1 i ster , T . , Ion-Molecule Reactions and Proton Affinities of

Methyl Thio- and Isothiocyanate,

Int. J. Mass Spectrom. Ion Phys. 15, 303 (1974).

Method used : ICR

Bracketing relative to (CH3)2C0 and 1-C4H8.

C2H3HS CAS REGN : 556-64-9

N##C*XSXXC

Thiocyanic acid, methyl ester (8CI9CI)

PA (exp) ' 189+/-6 kcal/mol Temperature • 300 K

McAl 1 i ster , T .

,

Ion-Molecule Reactions and Proton Affinities of

Methyl Thio- and Isothiocyanate,

Int. J. Mass Spectrom. Ion Phys. 15, 303 (1974).

Method used • ICR

Bracketing relative to (CH3)2C0 and 1-C4H8.
59

C2H4 CAS REGN : 74-85-1

C + + C

Ethene (9CI)

Ethylene ( 8CI

)

PA (exp) : 160.6 keal/mol Temperature : 298 K

Lossinq F. P., and Semeluk, G P. , Free Radicals by Mass Spectrometry. XLII. Ionization

Potentials and Ionic Heats of

Alkyl Radicals,

Can. J. Chem. 48, 955 (1970).

Formation for C1-C4

Method used : EM

Appearance potential of C2H5+ using EM.
60

C2H4F20 CAS REGN : 359-13-7

F##C**C*#0

*

#

F

Ethanol, 2 , 2-di f luoro- (8CI9CI)

GB (exp) : 170.1+/-2 kcal/mol Temperature '• 300 K

PA (exp) : 177.9+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. 1., and Taft, R. W.

,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C2H4F3N CAS REGN : 753-90-2

F

x

X FXXCXXC**N

xx

F

Ethanamine, 2 , 2 , 2-tr i f luoro- (9CI)

Ethyl amine, 2,2,2-trifluoro- (8CI)

GB (exp) • 188.9+/-2 kcal/mol

1

I Temperature : 293 K

PA (exp) : 197.9+/-2 kcal/mol I Temperature ;

1 298 K

Aue, D. H., Webb, H. M., and Bowers , M . T .

,

A Thermodynam i c Analysis of Solvation Effects on the

Basicities of Alkyla mines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Chem. Soc. 93, 318 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
62

GB (exp) : 191.9+/-2 kcal/mol Temperature : 300 K

PA (exp) ' 200.3+/-2 kcal/mol Temperature • 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

C2H4N2 CAS REGN : 540-61-4

| N**C**C#SN

Acetonitrile, amino- (8CI9CI)

1 PA (exp) : "197 kcal/mol Temperature • 300 K

Taagepera, M., Hehre, W. J., Topsom, R. D., and

Taft, R. W. Calculation of Polar Substituent Parameters by ab initio

Molecular Orbital Methods. Proton Affinities of

Substituted Primary Amines,

J. Am. Chem. Soc. 98, 7438 (1976).

Method used : ICR

Equilibrium; scale based on NH3
63

C2H40 | CAS REGN : 75-07-0

0++C**C

Acetaldehyde (8CI9CI)

PA (exp) 184+/-3 kcal/mol Temperature '

Harrison, A. G., Ivko, A., and Van Raalte, D.,

Energetics of Formation of Some Oxygenated Ions and

the Proton Affinities of Carbonyl Compounds,

Can. J. Chem. 44, 1625 (1966).

Method used • El

Electron impact fragmentation

PA (exp) • 186+/-1 kcal/mol Temperature 298 K

Refaey, K. M. A., and Chupka, W. A . , Photo i on i zat i on of the Lower Aliphatic Alcohols

with Mass Analysis,

J. Chem. Phys. 48, 5205 (1968).

Method used : PI

Appearance potential by IP fragmentation of C2H50H.

Continued on next page
PA (exp) : 189.4 kcal/mol Temperature : 298 K

Lo ssi ng , F. P. Heats of Formation of Some Isomeric [CnH2n + 103+

Ions. Substitutional Effects on Ion Stability,

J. Am. Chem. Soc. 99, 7526 (1977).

Method used : EM

Electron impact fragmentation (various molecules)

using EM. delta Hf(H+) = 365.7

GB (exp) '• 177.2+/-2 kcal/mol Temperature • 300 K

PA (exp) : 185+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.»

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. U.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
65

GB (exp) : 169.8+/-2 kcal/mol Temperature : 600 K

PA (exp) : 185.4+/-2 kcal/mol Temperature •' 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3

C2H40 | CAS REGN : 75-21-8

0

# x

x x CKXKKXC

Oxirane (9CI)

Ethylene oxide (8CI)

PA (exp) : 185+/-4 kcal/mol Temperature :

Beauchamp, J. L., and Dunbar, R. C.,

Identification of C2H5G+ Structural Isomers by

Ion Cyclotron Resonance Spectroscopy,

J. Am. Chem. Soc. 92, 1477 (1970).

Method used ’ ICR

Bracketing relative to CH30H and (CH3)20
66

1

I C2H402

1 CAS REGN : 64-19-7

1

1 oy.zc**c

y.%

0

Acetic acid (8CI9CI)

PA (exp) ‘ 188+/-3 kcal/mol Temperature '• 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used : MS

Equilibrium; scale based on NH3

GB (exp) : 171.8+/-2 kcal/mol Temperature : 600 K

PA (exp) : 188.2+/-2 kcal/mol Temperature ‘ 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used " MS

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
67

GB (exp) J 179.8+/-2 kcal/mol Temperature • 300 K

PA (exp) • 188+/-2 kcal/mol Temperature - 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ICR

Calculated entropy

Equilibrium; scale based on NH3

C2H402

—

CAS REGN : 107-31-3

0++C**0*xc

Formic acid, methyl ester (8CI9CI)

PA (exp) : 188+/-3 kcal/mol Temperature • 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some

J. Am. Chem. Soc. 95, 2427

Oxygenated Compounds,

( 1 973) .

Method used : MS

Bracketing relative to (CH3)20 and CH3CH0

Continued on next page
68

GB Cexp) • 179.0+/-2 kcal/mol Temperature • 300 K

PA Cexp) : 187+/-2 kcal/mol Temperature : 300 K

Harrison, A. G., Lin, P. H., and Tsang, C. W.,

Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry

,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used • MS

Equilibrium; scale based on CH3CH0

Entropy change assumed 2 ero

GB (exp) : 179.9+/-2 kcal/mol Temperature ’• 300 K

PA (exp) : 187.7+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
GB (exp) : 172.2+/-2 kcal/mol Temperature ' 600 K

i PA (exp) • 187.8+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used J MS

Calculated entropy

Equilibrium; scale based on NH3

[ C2H5Br

1 CAS REGN : 74-96-4

j C**C**BR

1 Ethane, bromo- (8CI9CI)

PA (exp) : 171+/-2 kcal/mol Temperature 300 K

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt, S. L.,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used : ICR

Bracketing and using also IP’s of H and C2H5BR

and assuming HA ( CH3BR+ ) =H A ( C2H5BR+ )

.
70

C2H5C1 CAS REGN : 75-00-3

CL*C**C

Ethane, chloro- (8CI9CI)

PA (exp) • 170+/-2 kcal/mol Temperature :

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt , S . L .

,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used ' ICR

Bracketing and using also IP’s of H and C2H5CL

and HA(CH3CL+)=HA(C2H5CL+)

.
I

I C2H5F

1 CAS REGN : 353-36-6

:

j F**C**C

| Ethane, fluoro- (8CI9CI)

PA (exp) : 165+/-5 kcal/mol Temperature : 300 K

Beauchamp, J. L., Holtz, D., Woodgate, S. D.,

and Patt , S. L.,

Thermochemi cal Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spec t ro scopy

,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used : ICR

Bracketing and using also the IP's of H and

C2H5F and assuming HA ( CH3F+ ) = HACC2H5F+).
72

C2H5F2N CAS REGN : 430-67-1

F**C**C**N

X

XF

Ethanamine, 2 , 2-di f luoro- (9CI)

Ethylamine, 2 , 2-di f luoro- (8CI)

GB Cexp) 5 197.5+/-2 kcal/mol Temperature 300 K

PA Cexp) : 205.9+/-2 kcal/mol Temperature ; 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
73

C2H5I CAS REGN : 75-03-6

. i*#c**c

Ethane, iodo- (8CI9CI)

PA (exp) s 175 keal/mol Temperature '• 30 0 K

Beauchamp, J. L., Holtz, D., Woodqate, S. D.,

and Patt , S . L .

,

Thermochemical Properties and Ion-Molecule Reactions

of the Alkyl Halides in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy,

J. Am. Chem. Soc. 94, 2798 (1972).

Method used : ICR

Bracketing and usinq also IP's of H and

assuming HA ( CH3I+ ) =HA ( C2H5I+ )

.
74

C2H5N CAS REGN : 151-56-4

N

x * X X CXXXXXC

Aziridine (9CI)

Ethylenimine (8CI)

GB ( exp) : 204.6+/-2 kcal/mol T emperature 300 K

PA ( exp) : 212.8+/-2 kcal/mol T emperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 204.9+/-2 kcal/mol T emperature 298 K

Taft, R. W.,

Proton-Transfer Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2.

Method used : ICR

Equilibrium; scale based on NH3

Continued on next page
75

PA (exp) 213+/-2 kcal/mol Temperature : 300 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Proton Affinities, Ionization Potentials, and

Hydrogen Affinities of Nitrogen and Oxygen Bases.

Hybridization Effects,

J. Am. Chem. Soc. 97, 4137 (1975).

Method used ; ICR

Equilibrium; scale based on CH3NH2

Van't Hoff plot

| C2H5N0

1 CAS REGN : 60-35-5

| N%%C**C

%

%

0

I Acetamide (SCI9CI)

GB (exp) : 1S8.5+/-2 kcal/mol Temperature : 600 K

PA (exp) : 205.7+/-2 kcal/mol Temperature ' 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of a 1 pha , omega-D i am i nes

,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Equilibrium; scale based on CH3NH2

Entropy change assumed zero
76

C2H5N0 CAS REGN : 123-39-7

ozy.cy.y.n**c

Formamide, N-methyl- (8CI9CI)

GB Cexp) : 195+/-4 kcal/mol Temperature : 300 K

PA Cexp) i 202.8+/-4 kcal/mol Temperature '• 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
77

1 C2H5N02

1

| CAS REGN : 79-24-3

1

| 0++N**C**C

j +

+

0

I Ethane, nitro- (8CI9CI)

1 1 1

1 1 1

PA (exp) : 186+/-2 kcal/mol i Temperature ' 300 K

Kriemler, P., and Buttrill,

Ion-Molecule Reactions and

of the Ni troalkanes,

J. Am. Chem. Soc. 95 , 1365

S. E. , Jr.,

the Proton Affinities

( 1973)

.

Method used • ICR

Bracketing relative to CH3CN and CH3CH0 .
78

C2H5N03 CAS REGN : 625-58-1

CXXC**0**N++0

++

0

Nitric acid, ethyl ester (8CI9CI)

PA (exp) i 181+/-3 kcal/mol Temperature • 300 K

Kriemler, P., and Buttrill, S. E., Jr.,

Positive and Negative Ion-Molecule Reactions and

the Proton Affinity of Ethyl Nitrate,

J. Am. Chem. Soc. 92, 1123 (1970).

Method used ’ ICR

Bracketing relative to cyclo-C6H10 and CH3N02.
79

C2H6 CAS REGN : 74-84-0

C**C

Ethane (8CI9CI)

1 PA (exp) : 128+/-1 kcal/mol Temperature :

Chong, S. !_., and Franklin, J L . , Heats of Formation of Protonated Cyc 1 opropane

,

Methyl cyclopropane, and Ethane,

J. Am. Chem. Soc. 94, 6347 (1972).

Method used : MS

By applying path deqeneracy correction found

delta H formation (C2H7+) = 218.8

Equilibrium relative to CH4; assume delta S = 0

PA (exp) : 139.6 (1) kcal/mol Temperature : 300 K

Hiraoka, K., and Kebarle, P.,

Stabilities and Energetics of Pentacoordi nated

Carbonium Ions. The Isomeric C2H7+ Ions and Some

Higher Analogues: C3H9+ and C4H11+,

J. Am. Chem. Soc. 98, 6119 (1976).

Method used : MS

Based on delta H f ormat i on ( C2H5+ ) = 219.

Equilibrium of reaction:

C2H5+ + H2 -> C2H7+(C-C protonation) (1).

Continued on next page
80

PA (exp) : 131.8 (2) kcal/mol Temperature :

Hiraoka, K., and Kebarle, P.»

Stabilities and Energetics of Pentacoordi nated

Carbonium Ions. The Isomeric C2H7+ Ions and Some

Higher Analogues: C3H9+ and C4H11+,

J. Am. Chem. Soc. 98, 6119 C1976).

Method used : MS

Based on delta H f ormat i on C C2H5+ ) = 219

Equilibrium of reaction:

C2H5+ + H2 + H2->C2H7+ + H2(CH protonation) (2)

C2H6FN CAS REGN : 406-34-8

FX*C*#C*XN

Ethanamine, 2-fluoro- (9CI)

Ethylamine, 2-^fluoro- (8CI)

GB (exp) : 201.8+/-2 kcal/mol Temperature : 300 K

PA (exp) : 210.2+/-2 kcal/mol Temperature s 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
! C2H6N2

1

1 CAS REGN : 4143-41-3

1

| C**N++N**C

I Diazene, dimethyl-, (E)- (9CI)

Azomethane , (E)~ (8CI)

I GB (exp) : 197.2+/-2 kcal/mol Temperature • 300 K

I PA (exp) : 204.5+/-2 kcal/mol Temperature : 300 K

Foster, M. S., Williamson, A. D., and Beauchamp, J. L.,

Photo i on i zat i on Mass Spectrometry of t ran s- Azomethane

,

Int. J. Mass Spectrom. Ion Phys. 15, 429 (1974).

Method used • MS

Calculated entropy

Equilibrium relative to NH3

I PA (exp) •' 206.8+/-5 kcal/mol Temperature • 300 K

Foster, M. S., and Beauchamp, J. L. , Gas-Phase Ion Chemistry of Azomethane by Ion 1 Cyclotron Resonance,

J. Am. Chem. Soc. 94, 2425 (1972).

Method used : ICR

Bracketing between NH3 and CH3NH2
82

C2H60 CAS REGN : 64-17-5

o**c**c

Ethanol (9CI)

Ethyl alcohol (3CI)

PA (exp) : 186+/-2 kcal/mol Temperature ’• 323-373 K

Long, J . , and Munson, B.,

Proton Affinities of Soma Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used ’ MS

Bracketing relative to CH3C00H and CH3CH0

GB (exp) : 178.4+/-2 kcal/mol Temperature • 300 K

PA (exp) : 186.2+/-2 kcal/mol Temperature : 300 K

Harrison, A. G. , Lin, P. H., and Tsang, C. W.

,

Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry

,

Int. J. Mass Spactrom. Ion Phys. 19, 23 (1976).

Method used • MS

Equilibrium; scale based on CH3CH0

Entropy change assumed zero Continued on next page
83

GB (exp) : 171.2+/-2 kcal/mol Temperature • 600 K

PA (exp) : 186.8+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ’ MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 178.9t/-2 kcal/mol Temperature : 300 K

PA (exp) : 186.7+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
84

C2H60 CAS REGN : 115-10-6

C*xo**C

Methane, oxybis- (9CI)

Methyl ether (8CI)

PA Cexp) • 190+/-4 kcal/mol Temperature • 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used ' MS

Bracketing relative to I-C4H8

Scale based on NH3

and CH3CH0;

PA (exp) ’ 189 kcal/mol Temperature '

Haney, M. A., and Franklin, J. L.,

Mass Spectrometr i c Determi nat i on of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used - MS

Delta H assume = 5X translational energy of

the products of reaction RH + RH+ -> RH2 + + R. Continued on next page
! GB (exp) • 181.3+/-2 kcal/mol Temperature ' 298 K

I PA (exp) : 189.1+/-2 kcal/mol Temperature • 298 K

Harrison, A. G., Lin, P. H., and Tsanq, C. W.,

Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry

,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used : MS

Equilibrium; scale based on MECHO

Entropy change assumed zero

I GB (exp) • 174.5+/-2 kcal/mol Temperature '• 60 0 K

I PA (exp) : 189.3+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Mea su r emen t s

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
86

GB (exp) • 182.7+/-2 kcal/mol T emperature ; 300 K

PA (exp) : 190. 1+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel , I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) • 193.3 kcal/mol Temperature • 300 K

Hiraoka, K., Grimsrud, E. P., and Kebarle, P.,

Gas Phase Ion Equilibria Studies of the Hydrogen

Ion in Watei—Dimethyl Ether and Methanol-Dimethyl,

J. Am. Chem. Soc. 96, 3359 (1974).

Method used ’ MS

Van't Hoff plot

Equilibrium relative to H20. Delta G

determined by means of thermodynamic cycles

involving mixed clusters.
87

C2H60S CAS REGN : 67-68-5

C**S*#C

+

+0

Methane, sulfinylbis- (9CI)

Methyl sulfoxide (8CI)

GB (exp) : 200.9+/-2.5 kcal/mol Temperature : 300 K

PA (exp) ' 208.3+/-2.5 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 18A+/-3 kcal/mol T emperatu re 30 0 K

McAllister, T

.

Ion Cyclotron Resonance Mass Spectroscopy of Dimethyl

Su 1 f ox i de

,

Intern. J. Mass Spectrom. Ion Phys. 25, 353 (1977).

Method used • ICR

Bracketing relative to CH30H and EtOH
88

I C2H6S CAS REGN : 75-08-1

j S#*c**c

Ethanethiol (8CI9CI)

GB (exp) • 180.8+/-2 kcal/mol Temperature • 300 K

PA (exp) • 189.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
89

C2H6S CAS REGN : 75-18-3

; c**s**c

Methane, thi obi s~ (9CI)

Methyl sulfide (8CI)

GB (exp) • 190.2+/-2 kcal/mol Temperature : 300 K

PA (exp) ; 197.6+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.»

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
90

C2H7N CAS REGN : 75-04-7

N**C**C

Ethanamine (9CI)

Ethylamine (8CI)

GB (exp) • 205.6+/-2 kcal/mol Temperature ' 300 K

PA (exp) : 214.0+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel , Taaqepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 205.9+/-2 kcal/mol Temperature : 298 K

PA (exp) • 214.3+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
91

C2H7N

I CAS REGN :

L 124-A0-3

C**N#*C

Methanami ne, N-methyl- (9CI)

Di methylami ne (8CI)

GB (exp) : 209.7+/-2 kcal/mol T emperature : 30 0 K

PA (exp) ’ 217.9+/-2 kcal/mol T emperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 209.5+/-2 kcal/mol T emperature : 298 K

PA (exp) ’ 217.7+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

9 Potentials,

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

Corvtinued on next page
92

GB ( exp

)

: 203.4+/-2 kcal/mol Temperature • 600 K

PA ( exp

)

: 220.6+/-2 kcal/mol Temperature • 600 K

Briggs, J. P., Yamdagni, R., and Kebarle, P.,

Intrinsic Basicities of Ammonia, Methylami nes. Anilines, and Pyridine from Gas-Phase ProtonExchange Equilibria,

J. Am. Chem. Soc. 94, 5128 (1972).

Method used ' MS

Entropy change assumed zero Equilibrium; scale based on NH3

C2H7P CAS REGN : 676-59-5

C##P#*C

Phosphine, dimethyl- (8CI9CI)

GB (exp) : 205.6+/-2 kcal/mol Temperature '• 298 K

Taft, R. W.,

Proton-Transfer Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2.

Method used s ICR

Equilibrium; scale based on NH3
93

C2H8N2 I CAS REGN * 57- K7

C**N**C

x

x

N

Hydrazine, 1 , 1-di methyl- (8CI9CI)

GB C exp) : 209.5+/-2 kca 1/mo 1 T emperature 30 0 K

PA ( exp

)

: 217.3+/-2 kcal/mol T emperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
94

C2H8N2 CAS REGN 107-15-3

N#*C**C*#N

1 , 2- Ethaned i am i ne (9CI)

Ethylenedi ami ne (8CI)

GB (exp) : 213.60+/-2 kcal/mol Temperature ’ 298 K

PA (exp) ’ 216.50+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quant i tat i ve Evaluat i on of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

GB (exp) : 215.50+/-2 kcal/mol Temperature • 298 K

PA (exp) • 227.50+/-2 kcal/mol Temperature • 298 K

Yamdagni, R., and Kebarle, P.»

Gas-Phase Basicities of Amines. Hydrogen Bonding

i n Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha, omega-Diamines,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used ’• MS

Equilibrium; scale

Van't Hoff plot

based on (CH3)3N
95

C3D9N CAS REGN : 13960-80-0

C*#N**C

KXC

Methan-d3-ami ne , N , N-d i ( methyl -d3 ) - (9CI)

Tr i methylami ne-d9 (8CI)

GB (exp) ’ 214.00+/-2 kcal/mol Temperature ’ 298 K

Taft, R. W.,

Proton-Transf er Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2.

Method used ’ ICR

Equilibrium; scale based on NH3
96

C3H2N2 CAS REGN : 109-77-3

N##C**C**C##N

Propanedi n i tr i le (9CI)

Ma 1 onon i t r i 1 e (8CI)

GB (exp) ’ 169.5+/-2 kcal/mol Temperature * 300 K

PA (exp) : 177.7+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 54 1 7 C1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
97

C3H3F302 CAS REGN : 431 -47 -0

F

*

K C#*0**C**C**F

+ K + *

0 F

Acetic acid, trifluoro-, methyl ester (8CI9CI)

GB (exp) : 172.5+/-2 kcal/mol Temperature • 300 K

PA (exp) : 180.3+/-2 kca 1/mo 1 Temperature ’ 300 K

Wolf, J. F., Staley, R. H . , Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
98

C3H3F302 CAS REGN : 32042-38-9

F

x

x F*xc**C**0**C++0

x

xF

Ethanol, 2 , 2 , 2-tri f luoro-, formate (9CI)

GB (exp) • 173+/-2 kcal/mol Temperature : 300 K

PA (exp) : 180.8+/-2 kcal/mol Temperature • 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
99

C3H3N CAS REGN : 107-13-1

C++C**C##N

2-Propeneni tri le (9CI)

Acryloni tri le (8CI)

GB (exp) * 180.1+/-2 kcal/mol Temperature • 300 K

PA (exp) ’ 187.9+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5A17 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 188.3+/-2.5 kcal/mol T emperature 300 K

Staley, R. H . , Kleckner, J. E., and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used ’ ICR

Calculated entropy

Equilibrium relative to C3H6 02 ( 1 , 3-D i oxo 1 ane ) with

its PA value = 189.8; relative to Et CHO and MeCN
100

C3H4 CAS REGN : 74-99-7

c##c**c

1-Propyne ( 9CI

)

Propyne (8CI

)

PA (exp) • 176+/-2 kcal/mol Temperature • 300 K

Aue, D. H., Davidson, W. R., and Bowers, M. T.,

Heats of Formation of C3H5+ Ions. Allyl, Vinyl, and

Cyclopropyl Cations in Gas-Phase Proton-Transfer

React ions,

J. Am. Chem. Soc. 98, 6700 (1976).

Method used • ICR

Entropy change assumed zero Equilibrium; scale based on H2S.
C3H4 CAS REGN : 463-49-0

C++C++C

1 , 2-Propadi ene (9CI)

Allene (SCI)

PA (exp) : 176+/-2 kcal/mol Temperature • 300 K

Aue, D. H . , Davidson, W. R., and Bowers, M. T.,

Heats of Formation of C3H5+ Ions. Allyl, Vinyl, and

Cyclopropyl Cations in Gas-Phase Proton-Transfer Reactions,

J. Am. Chem. Soc. 98, 6700 (1976).

Method used ' ICR

Equilibrium; scale based on H2S.

Entropy change assumed zero.
C3H4 CAS REGN : 2781-85-3

C

* +

# + C#****C

Cyclopropene (8CI9CI)

PA (exp) 194+/-3 kcal/mol T emperature 300 K

Aue, D. H., Davidson, W. R., and Bowers, M. T.,

Heats of Formation of C3H5+ Ions. Allyl, Vinyl, and

Cyclopropyl Cations in Gas-Phase Proton-Transfer Reactions,

J. Am. Chem. Soc. 98, 6700 C1976).

Method used : ICR

Bracketing relative to (CH3)20 and (C2H5)20.
103

C3H9C1N CAS REGN : 592-76-7

N##C**C**C**CL

Propaneni tri le, 3-chloro- (9CI)

Propi on i tr i le, 3-chloro- (8CI)

PA (exp) ’ 181.1+/-2 kcal/mol Temperature • 300 K

Staley, R. H., Kleckner, J. E., and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used ’ ICR

Calculated entropy

Equilibrium relative to MeCN

GB (exp) : 178.3+/-2 kcal/mol Temperature : 300 K

PA (exp) : 186.1+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5917 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
104

C3H5N CAS REGN : 107-1-2-0

C**C**C##N

Propanen i tr i le (9CI)

Propi on i tr i le (8CI)

GB (exp) : 182.4+/-2 kcal/mol 'Temperature : 300 K

PA (exp) : 190.2+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 190.2+/-2.5 kcal/mol Temperature •' 300 K

Staley, R. H.» Kleckner, J. E., and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used • ICR

Calculated entropy

Equilibrium relative to n-PrCN, HC02Et, i-PrCHO,

Me20, EtCHO and relative to 1,3-Dioxane using

its PA = 189.8
105

C3H5N CAS REGN : 2450-71-7

C##C**C*#N

2-Propyn- 1-ami ne (9CI)

2-Propynylami ne (8CI)

GB (exp) : 200.6+/-2 kcal/mol Temperature : 300 K

PA (exp) 5 209.0+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
106

C3H6 CAS REGN : 75-19-4

C

* K

X * C*xx**C

Cyclopropane (8CI9CI)

PA (exp) : 180.6+/-4 kcal/mol Temperature : 340 K

Chong, S. L., and Franklin, J. L.,

Hea-ts of Formation of Protonated Cyclopropane,

Methylcyclopropane, and Ethane,

J. Am. Chem. Soc. 94, 6347 (1972).

Method used • MS

HC(0H)2+ + C-C3H6 -> HCOOH + C-C3H7+.

Equilibrium of reactions:

CH30H2+ + C-C3H6 -> (JU30H + C-C3H7+

;

Apply correction for -path degeneracy,

delta S=0.

Assumi ng
107

C3H6 CAS REGN : 1 15-07- 1

c++c**c

1-Propene (9CI)

Propene (8CI)

PA (exp) i 180 kcal/mol Temperature • 298 K

Lossing F. P., and Semeluk, G P. Free Radicals by Mass Spect r omet ry . XLII. Ionization

Potentials and Ionic Heats of Formation for C1-C4

Alkyl Radicals,

Can. J. Chem. 48, 955 (1970).

Method used : EM

Appearance potential of C3H7+.

PA (exp) • 182.2+/-2 kcal/mol Temperature : 340 K

Chong, S. L., and Franklin, J L. , Heats of Formation of Protonated Cyclopropane,

Methylcyclopropane, and Ethane,

J. Am. Chem. Soc. 94, 6347 (1972).

Method used ’ MS

Correction for path degeneracy.

Equilibrium relative to CH30H; assuming

delta S = 0. Continued on next page
108

GB (exp) • 165.4+/-2 kcal/mol Temperature * 600 K

PA (exp) • 182.6+/-2 kcal/mol Temperature : 600 K

Yamdagni , R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ' MS

Equilibrium; scale based on NH3

Entropy change assumed zero

C3H6F3N CAS REGN : 460-39-9

F

*

X N*#C#*C**C##F

X

X

F

1-Propanami ne, 3 , 3 > 3-t r i f luoro- (9CI)

Propylamine, 3 , 3 , 3~tr i f luoro- (8CI)

GB (exp) • 200.6+/-2 kcal/mol Temperature • 300 K

PA (exp) : 209.0+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
109

C3H6F3N CAS REGN : 677-41-8

F C

* x

* x . F*#C**N**C

*X

F

Methanamine, 1, 1, 1-trifluoro-N»N-di methylPA (exp) s 192+/-3 kcal/mol Temperature '• 300 K

Staley, R. H., Taagepera, M., Henderson, W. G.,

Koppel, I., Beauchamp, J. L., and Taft, R. W. Effects of Alkyl and Fluoroalkyl Substitution on the Heterolytic and Homolytic Bond Dissociation

Energies of Protonated Amines,

J. Am. Chem. Soc. 99, 326 (1977).

Method used • ICR

Calculated entropy

Equilibrium scale based on NH3
110

C3H6F3N CAS REGN : 2730-67-8

F

#

* C*#N*#C#*C#*F

#*

F

Ethanami ne, 2 , 2, 2-tr i f luoro-N-methyl- (9CI)

Ethylamine, 2 , 2 , 2~tr i f luoro-N-methyl- (8CI)

GB (exp) ’ 199.6+/-2 kcal/mol Temperature * 300 K

PA (exp) : 207.8+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
C3H6N2 CAS REGN : 151-18-8

N##C#*C**C**N

Propaneni tri le, 3-amino- (9CI)

Propi oni tr i le, 3-amino- (8CI)

GB (exp) : 196.1+/-2 kcal/mol Temperature : 300 K

PA (exp) : 204.5+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used * ICR

Calculated entropy

Equilibrium; scale based on NH3

C3H6N2 CAS REGN : 5616-32-0

C**N**C*#C##N

Acetonitrile, ( methylami no ) - (8CI9CI)

GB (exp) ' 196.1+/-2 kcal/mol Temperature : 300 K

PA (exp) ; 20A.3+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used - ICR

Calculated entropy

Equilibrium; scale based on NH3
C3H60 CAS REGN : 67-64-1

c**c**c

++

0

2-Propanone (9CI)

Acetone (8CI)

PA (exp) ' 195.7+/-2 kcal/mol Temperature • 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 C 1 97 3) .

Method used • MS

Bracketing relative to (C2H5)20 and CH2C0

PA (exp) 193.6+/— 1 kcal/mol Temperature • 350 K

Ausloos, P., and Lias, S. G. The Proton Affinity of Ketene and the Heat of

Formation of CH3C0+,

Chem. Phys. Letters 51, 53 (1977).

Method used • ICR

Equilibrium; scale based on PA (iso~C4H8) = 193.5+/-1

Continued on next page
113

GB not calculated for this reference

PA (exp) ' 188 kcal/mol Temperature :

Haney, M. A., and Franklin, J. L.,

Mass Spectrometr i c Determination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used : MS

Delta H estimated equal 5 times

translational energy of the products.

PA (exp) • 196 kcal/mol Temperature : 298 K

Heats of Formation of Some Isomeric [CnH2n + 10]+

Ions. Substitutional Effects on Ion Stability,

J. Am. Chem. Soc. 99, 7526 (1977).

Method used • EM

Electron impact fragmentation (various molecules)

using EM. delta Hf(H+) = 365.7

Lossi ng, F. P

.

Continued on next page
GB (exp) • 179+/-2 kcal/mol Temperature • 600 K

PA (exp) : 193.8+/-2 kcal/mol Temperature s 600 K

Yamdagni , R., and Kebarle, P.,

Gas-Phase Basicities and Pro-ton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 186.5+/-2 kcal/mol Temperature ; 300 K

PA (exp) : 193.9+/-2 kcal/mol Temperature ’• 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.»

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
C3H60 CAS REGN : 123-38-6

c**c**c++o

Propanal (9CI)

Propi onaldehyde (8CI)

PA (exp) • 190+/-3 kcal/mol Temperature •

Harrison, A. G., Ivko, A., and Van Raalte, D.,

Energetics of Formation of Some Oxygenated Ions and

the Proton Affinities of Carbonyl Compounds,

Can. J. Chem. A<+, 1625 ( 1966 ).

Method used : El

Electron impact f ragmentat i on of various molecules.

PA (exp) : 187 kcal/mol T emperature 298 K

Lossing, F. P. Heats of Formation of Some Isomeric [CnH2n + 10]+

Ions. Substitutional Effects on Ion Stability,

J. Am. Chem. Soc. 99, 7526 (1977).

Method used • EM

Electron impact fragmentation (various molecules)

using EM. delta Hf(H+) = 365.7

Continued on next page
1 16

GB (exp) • 172.3+/-2 kcal/mol Temperature : 600 K

PA (exp) • 187.9+/-2 kcal/mol Temperature *• 600 K

Yamdagni, R.» and Kebarle, P.»

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 180.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 188+/-2 kcal/mol Temperature •' 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
C3H60 CAS REGN : 503-30-0

c**o

X X

X X Cxxc

Oxetane (9CI)

Trimethylene oxide (8CI )

PA (exp) : 1 94+/-

1

kcal/mol Temperature • 300 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Proton Affinities, Ionization Potentials, and

Hydrogen Affinities of Nitrogen and Oxygen Bases.

Hybr i di zat i on Effects,

J. Am. Chem. Soc. 97, 4137 (1975).

Method used : ICR

Sem i quant i tat i ve . Absolute value assign

relative to CH3CH0 and (CH3)2C=CH2.
C3H60S CAS REGN : 1534-08-3

c**c**s**c

+

+

0

Ethanethioic acid, S-methyl ester

Acetic acid, thio-, S-methyl ester

( 9CI

)

( 8CI

)

PA (exp) * "197+/-2 kcal/mol Temperature ' 300 K

Grunwell, J. R., Foerst, D. L., Kaplan, F., and

S i dd i gu i , J

.

The Relative Basicity of Sulfur containing Esters,

Tetrahedron 33, 2781 (1977).

Method used '• ICR

Bracketing relative to MeCOOMe and MeC0NHCH3. Also

found the reactions of Me2S with MeCOOMe and MeCOSMe

are both thermoneutral concluded PA (CH3C0SCH3)

is within 2 kcal of that of PA (MeCOOMe)
119

C3H602

1 CAS REGN : 79-09-4

oxxc**c**c

X

X

0

Propanoic acid (9CI)

Propionic acid (8CI)

GB (exp) • 173.9+/-2 kcal/mol Temperature : 600 K

PA (exp) : 191.1+/-2 kcal/mol Temperature • 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Equilibrium; scale based on NH3

Entropy change assumed zero
120

C3H602 CAS REGN : 79-20-9

C#*C**0**C

+

+0

Acetic acid, methyl ester (8CI9CI)

PA (exp) J 194+/-2 kcal/mol Temperature : 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to ME2C0 and CH2C0

GB (exp) : 186.7+/-2 kcal/mol Temperature : 298 K

PA (exp) s 194.1+/-2 kcal/mol Temperature : 298 K

Harrison, A. G., Lin, P. H., and Tsang, C. W.,

Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used * MS

Equilibrium; scale based on (CH3)2C0

Entropy change assumed zero Continued on next page
121

GB (exp) : 187.6+/-2 kcal/mol Temperature : 300 K

PA (exp) : 195.4+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used •' ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) ' 179.8+/-2 kcal/mol Temperature * 600 K

PA (exp) • 195.4+/-2 kcal/mol Temperature • 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ' MS

Calculated entropy

Equilibrium; scale based on NH3
122

C3H602 CAS REGN : 109-94-4

o++c**o#*c**c

Formic acid, ethyl ester (8CI9CI)

PA (exp) • 194+/-2 kcal/mol Temperature ’• 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to CH2C0 AND I-C4H8;

scale based on NH3.

GB (exp) 183.7+/-2 kcal/mol Temperature : 298 K

PA (exp) • 191.1+/-2 kcal/mol Temperature • 298 K

Harrison, A. G., Lin, P. H., and Tsang, C. l*J., Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used ’ MS

Equilibrium; scale based on (CH3)2C0

Entropy change assumed zero Continued on next page
123

GB (exp) • 175.6+/-2 kcal/mol Temperature : 600 K

PA (exp) : 191.2+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 183.4+/-2 kcal/mol Temperature : 300 K

PA (exp) • 191.2+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.>

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
124

C3H603 CAS REGN : 616-38-6

C*X0**C**0**C

++

0

Carbonic acid, dimethyl ester (8CI9CI)

GB (exp) : 189.8+/-2 kcal/mol Temperature : 300 K

PA (exp) • 197.2+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
125

C3H652 CAS REGH : 2168-84-5

S

+

+ C#*S****C**C

Ethane( di thi oi c)aci d, methyl ester

PA (exp) * >197+/-2 kcal/mol Temperature • 300 K

Grunwell, J. R., Forest, D. L , Kaplan , F . , and

S i dd i gu i , J . The Relative Basicity of Sulfur Containing Esters,

Tetrahedron 33, 2781 (1977).

Method used : ICR

Double resonance technique shows PA (MeCSSMe) > PA

(the COSMe)
126

C3H7N CAS REGN : 107-1 1-9

C++C*#C#*N

2-Propen- 1-ami ne (9CI)

Allylamine (8CI)

GB (exp) s 205.3+/-2 kcal/mol Temperature • 300 K

PA (exp) : 213.7+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

tlclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
127

C3H7N CAS REGN : 503-29 -7

C**N

* * X X CX*C 1

Azetidine (8CI9CI)

GB Cexp) • 211.9+/-2 kcal/mol T emperatu re : 300 K

PA (exp) s 220.1+/-2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taagepera

,

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) ' 212.2+/-2 kcal/mol Temperature : 290 K

PA (exp) • 220.+/-2 kcal/mol T emperature : 290 K

Bowers, M. T., Aue, D. Equilibrium Constants

Accurate Determination

J. Am. Chem. Soc. 93,

H. , and Webb, H. M.

for Gas-Phase Ionic

of Relative Proton

9314 (1971).

fReact ions.

Affinities,

Method used : ICR

Entropy change assumed zero Equilibrium; scale based on (CH3)3N
128

C3H7N CAS REGN : 1072-44-2

C

x x

X X NxxxXxc

Aziridine, 1-methyl- (8CI9CI)

PA (exp) • 219.4+/-2 kcal/mol Temperature • 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Proton Affinities, Ionization Potentials, and

Hydrogen Affinities of Nitrogen and Oxygen Bases.

Hybridization Effects,

J. Am. Chem. Soc. 97, 4137 (1975).

Method used • ICR

Equilibrium; scale based on CH3NH2
129

C3H7N0 CAS REGN : 68-12-2

C**N**C++0

*#

C

Formamide, N , N-di methyl- (8CI9CI)

GB (exp) s 201.2+/-3 kcal/mol Temperature • 300 K

PA (exp) ’ 209.0+/-3 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used * ICR

Calculated entropy

Equilibrium; scale based on NH3
130

1

! C3H8 CAS REGN : 74-98-6

C**C**C

Propane (8CI9CI)

PA (exp) : 148.2 kcal/mol Temperature : 163-213 K

Hiraoka, K., and Kebarle, P.,

Information on the Proton Affinity and Protolysis

of Propane from Measurement of the Ion Cluster,

Equilibrium: C2H5+ + CH4 = C3H9+.

Can. J. Chem. 53, 970 (1975).

Method used : MS

Equilibrium of reaction

C2H5+ + 2CH4 -> C3H9+ + CH4

Van't Hoff plot

PA (exp) : 143 kcal/mol Temperature : 170 K

Field, F. H., and Begqs, D. P.,

Reversible Reactions of Gaseous Ions. III. Studies

with Methane at 0. 1-1.0 Torr and 77-300 K,

J. Am. Chem. Soc. 93, 1585 (1971).

Method used : MS

Equilibrium of reaction:

C2H5+ + CH4 -> C3H9+

.

Based on delta H formati on(C2H5+ )

.

Calculated entropy

Continued on next page
131

GB not calculated for this reference

PA (exp) 2 <152.8 kcal/mol Temperature 2 "170 K

Hiraoka, K., and Kebarle, P.,

Stabilities and Energetics of Pentacoordi nated

Carbonium Ions. The Isomeric C2H7+ Ions and Some

Higher Analogues 2 C3H9+ and C4H11+,

J. Am. Chem. Soc. 98, 6119 (1976).

Method used : MS

Calculated entropy

Equilibrium of reaction

Sec-C3H7+ + H2 -> C3H9+

Based on delta H f ormat i on ( C3H7+ )

;

C-H protonat i on

| C3H80

nr

I CAS REGN

1 67-63-0

Cxxcxxc

xx

0

2-Propanol (9CI)

Isopropyl alcohol (8CI)

PA (exp) 2 192+/-2 kcal/mol T emperature 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used 2 MS

Bracketing relative to I-C4H8 and (CH3)20

Continued on next page
132

GB not calculated for this reference

PA (exp) : 190 kcal/mol Temperature •

Hiraoka, K., and Kebarle, P. Condensation Reactions Involving Carbonium Ions and

Lewis Bases in the Gas Phase. Hydration of the

tert-Butyl Cation,

J. Am. Chem. Soc. 99, 360 (1977).

Method used • MS

Equilibrium relative to known standard acids

C3H80 CAS REGN : 71-23-8

Cxxcxxcxxo

1-Propanol (9CI)

Propyl alcohol (8CI)

GB (exp) : 181.0+/-2 kcal/mol Temperature : 300 K

PA (exp) • 188.8+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
133

PA (exp) • 189+/-2 kcal/mol Temperature • 323-373 K

Long, J., and Munson, B.»

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to C2H50H and ( CH3 ) 20

C3H80 CAS REGN : 540-67-0

c**c**o**c

Ethane, methoxy- (9CI)

Ether, ethyl methyl (8CI)

GB (exp) • 186.2+/-2 kcal/mol Temperature : 300 K

PA (exp) ‘ 194+/-2 kcal/mol Temperature • 300 K

Wolf, J. F.> Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
134

. C3H8S CAS REGN : 75-33-2

C#*C*XC

XXS

2-Propanethiol (8CI9CI)

GB (exp) ’ 184.2+/-2 kcal/mol Temperature ‘ 300 K

PA (exp) '• 192+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

C3H8S CAS REGN : 107-03-9

Cxxcxxcxxs

1-Propanethi ol (8CI9CI)

GB (exp) ’ 181.9+/-2 kcal/mol Temperature : 300 K

PA (exp) : 189.7+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used s ICR

Calculated entropy

Equilibrium; scale based

/ on NH3
135

C3H8S CAS REGN : 624-89-5

c##c#*s##c

Ethane, (methylthi o )- (9CI)

Sulfide, ethyl methyl (8CI)

GB Cexp) ' 192.9+/-2 kcal/mol Temperature : 300 K

PA (exp) • 200.7+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
136

C3H9As CAS REGN : 593-88-4

C*#AS*C

x

KC

Arsine, trimethyl- (8CI9CI)

PA (exp) ’ 210.6 kcal/mol Temperature • 300 K

Hodges, R. V., and Beauchamp, J. L.»

Basicity and Ion-Molecule Reactions of Tr i methylarsi ne

in the Gas Phase Determined by Ion Cyclotron

Resonance Spectroscopy,

Inorg. Chem. 14, 2887 (1975).

Method used ' ICR

Equilibrium relative to CH3NH2 and also

to CF3(CH2)3NH2.
137

C3H9N CAS REGN : 75-31-0

C#XC*#C

X

XN

2-Propanami ne C 9CI

)

Isopropylamine (8CI)

GB (exp) ’ 208.1+/-2 kcal/mol Temperature • 300 K

PA (exp) ’• 216.5+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) s 208.2+/-2 kcal/mol Temperature s 298 K

PA (exp) ’ 216.6+/-2 kcal/mol Temperature •* 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
138

C3H9N CAS REGN : 75-50-3

C#*N*XC

xxC

Methanamine, N,N-dimethyl- (9CI)

Tr i methylami na (8CI)

GB (exp) : 214.30+/-2 kcal/mol Temperature ’ 300 K

PA (exp) : 222.10+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 213.70+/-2 kcal/mol Temperature ' 298 K

PA (exp) s 221.50+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

Continued on next page
139

GB (exp) • 208.40+/-2 kcal/mol Temperature : 600 K

PA (exp) 225.60+/-2 kcal/mol Temperature • 600 K

Briggs, J. P., Yamdagni, R., and Kebarle, P.,

Intrinsic Basicities of Ammonia, Methylami nes. Anilines, and Pyridine from Gas-Phase ProtonExchange Equilibria,

J. Am. Chem. Soc. 94, 5128 (1972).

Method used ’• MS

Entropy change assumed zero Equilibrium; scale based on NH3

C3H9H CAS REGN : 107-10-8

CX*C*#C#*N

1-Propanami ne (9CI)

Propylamine (8CI)

GB (exp) • 207.1+/-2 kcal/mol Temperature • 300 K

PA (exp) • 215.5+/-2 kcal/mol Temperature ‘ 300 K

Unpublished work by Wolf* Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
- 140 -

GB (exp) : 207.3+/-2 kcal/mol Temperature : 300 K

PA (exp) - 215.7+/-2 kcal/mol Temperature : 300 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

C3H9N CAS REGN : 624-78-2

CXXC#*N##C

Ethanamine, N-methyl- (9CI)

Ethylamine, N-methyl- (8CI)

GB (exp) : 212.2+/-2 kcal/mol Temperature ’• 300 K

PA (exp) ’ 220.4+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
GB (exp) ’ 212+/-2 kcal/mol Temperature ’ 298 K

PA (exp) : 220.2+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

C3H9N0 CAS REGN : 109-85-3

Cx#0##C**C##N

Ethanamine, 2-methoxy- (9CI)

Ethylamine, 2-methoxy- (SCI)

GB (exp) ' 209.3+/-2 kcal/mol Temperature : 298 K

PA (exp) : 221.0+/-2 kcal/mol Temperature • 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
1*2

C3H9P CAS REGN : 594-09-2

CxxpxxC

X

XC

Phosphi ne. trimethyl- (8CI9CI)

GB (exp) : 21*.9+/-2 kcal/mol Temperature : 298 K

Taft, R. W.,

Proton-Transfer Reactions,

Ed. E. F. Caldin and V. Gold,

(John UJiley and Sons, New York, 1975) Ch. 2.

Method used : ICR

Equilibrium; scale based on NH3

PA (exp) : 223.3+/-2 kcal/mol T emperature 300 K

Staley, P. H., and Beauchamp, J. L. Basicities and Ion-Molecule Reactions of the

Methylphosphi nes in the Gas Phase by Ion Cyclotron

Resonance Spectroscopy,

J. Am. Chem. Soc. 96, 6252 (197*).

Method used * ICR

Bracketing relative to (CH3)3N and (CH3)2C2H5N
143

C3H10N2 CAS REGN : 109-76-2

N#KC##C#*C#XN

1 , 3-Propanedi ami no (8CI9CI)

GB (exp) : 219.10+/-2 kcal/mol Temperature * 298 K

PA (exp) s 231.60+/-2 kcal/mol Temperature : 298 K

Aue, D. H . , Webb, H. M.» and Bowers, M. T.,

Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

GB (exp) : 221.10+/-2 kcal/mol Temperature • 298 K

PA (exp) - 235.10+/-2 kcal/mol Temperature • 298 K

Yamdagni , R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha , omega-Di am i nes

,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Equilibrium; scale based on (CH3)3N

Van't Hoff plot
C4H4F402 CAS REGN : 1683-88-1

FX

X F*XC**C**0*#C*XC*XF

x + x +

F 0

Acetic acid, trifluoro -

, 2-f luoroethyl ester (8CI)

GB (exp) : 172.3+/-2 kcal/mol Temperature 300 K

PA (exp) • 180.1+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used s ICR

Calculated entropy

Equilibrium; scale based on NH3
145

C4H4N2 CAS REGN : 289-80-5

C. .N

C* * H

c. .c’

Pyridazine (8CI9CI)

GB (exp) : 206.4+/-2 kcal/mol Temperature • 300 K

PA (exp) •' 213.8+/-2 kcal/mol Temperature ’• 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
146

C4H4N2CAS REGH : 289-95-2

N. .C

c’

’ N

c. .c’

Pyrimidine C8CI9CI)

GB (exp) : 201.2+/-2 kcal/mol Temperature : 300 K

PA (exp) * 208.6+/-2 kcal/mol Temperature '• 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C4H4N2 CAS REGN : 290-37-9

N. .C

o o

* C . . N

*

Pyrazine C8CI9CI)

6B (exp) : 199.0+/-2 kcal/mol Temperature : 300 K

PA (exp) ' 206.4+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley* Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C4H4N20 CAS REGN : 557-01-7

C

S C

o'/.y.c c V

2( 1H)-Pyrimi di none (8CI9CI)

PA (exp) • 207+/-5 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used : MS

Bracketing relative to NH3 and CH3NH2.
C4H4N202 CAS REGN : 66-22-8

C

cmc

N

czzo

2 , A C 1H , 3H )-Pyr i mi di nodi one (9CI)

Uracil (8CI)

PA (exp) - 207+/-5 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used ; MS

Bracketing relative to NH3 and CH3NH2
150

C4H40 CAS REGN : 1 10-00-9

CxxxxxO

+ x

+ x C C

x +

* +

C

Furan (8CI9CI)

PA (exp) : 189.8+/-2 kcal/mol Temperature : 300 K

Chong, S. L., and Franklin, J L. , Proton Affinities of Benzene, Toluene, and the Xylenes,

J. Am. Chem. Soc. 94, 6630 (1972).

Method used • MS

Entropy change assumed zero Equilibrium relative to (CH3)20.
151

C4H5F302 CAS REGN : 383-63-1

F

X

X FXXC**C*#0#*C**C

x +

x + F 0

Acetic acid, trifluoro-, ethyl ester (8CI9CI)

GB (exp) : 175.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 183.2+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H . , Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.

,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on NH3
152

C4H5N | CAS REGN : 109-97-7

CXXXXXN

x +

1 H-Pyrro 1 e (9CI)

Pyrrole (8CI)

GB (exp) ’ 197.9+/-2 kcal/mol Temperature * 298 K

PA (exp) J 205.9+/-2 kcal/mol Temperature • 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

GB (exp) •’ 192.2+/-2 kcal/mol Temperature : 600 K

PA (exp) : 209.4+/-2 kcal/mol Temperature : 600 K

Yamdaqni , R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha , omeqa-Di ami nes,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Equilibrium; scale based on NH3

Entropy change assumed zero
153

C4H5N CAS REGN 5500-2 1-0

C

X X

X X CXXXXXC

N##C

CyclopropanecarbonitrilQ (8CI9CI)

1

PA (exp) • 193.2+/-2 kcal/mol Temperature ‘ 300 K

Staley, R. H., Kleckner, J. E., and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used *• ICR

Calculated entropy

Equilibrium relative to HC02-n-C4H9

GB (exp) s 185.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 193.2+/-2 kcal/mol Temperature • 300 K

Wolf, J. F.» Staley, R. H., Koppel, I., Taagepera, M.»

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
154

C4H5N02 CAS REGN : 623-49-4

1 N##C**C**0**C**C

++

0

Carbonocyani di c acid, ethyl ester (9CI)

Formic acid, cyano -

, ethyl ester (8CI)

GB (exp) : 173.1+/-2 kcal/mol Temperature '• 300 K

PA (exp) • 180.9+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
155

o

C4H5N30

C

c’ N

H'/.ZC C'/.V.O

CAS REGN : 71-30-7

N

2 ( 1H ) -Pyr i mi di none , 4-amino- (9CI)

Cytosine (8CI)

PA (exp) : 220+/-2 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J . A. , Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used • MS

Bracketing relative to (CH3)2NH and (CH3)3N.
156

1

I C4H6N2 CAS REGN : 616-47-7

L_

C+++++N

* X

X X

I C**N C

x + X + C

I 1H~Imi dazole, 1-methyl- (9CI)

I Imidazole, 1-methyl- (8CI)

GB (exp) s 217.3+/-2 kcal/mol Temperature ; 300 K

PA (exp) • 225.1+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
157

C4H7F30 CAS REGN : 461-24-5

F

XX Fxxcxxcxxoxxcxxc

XXF

Ethane. 2-ethoxy- 1 , 1 , 1-tri fluoro- (9CI)

Ether, ethyl 2 , 2 , 2-tr.i f luoroethyl (8CI)

GB Cexp) ’ 177.1+/-2 kcal/mol Temperature ’ 300 K

PA (exp) : 184.9+/-2 kcal/mol Temperature ‘ 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
158

C4H7N

C**C**C##N

XxC

| CAS REGN : 78-82-0

P r opanen i t r i 1 e , 2-methyl- (9CI)

Isobutyroni tri le (8CI)

PA (exp) • 192.2+/-2 kcal/mol Temperature : 300 K

Staley, R. H., Kleckner, J. E , and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used : ICR

Calculated entropy

Equilibrium relative to HC02C2H5

GB (exp) • 184.4+/-2 kcal/mol Temperature : 300 K

PA (exp) • 192.2+/-2 kcal/mol Temperature '• 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
159

C4H7N CAS REGN : 109-74-0

N##C#*C**C**C

Butanen i tr i le (9CI)

Butyroni tri le (8CI)

PA (exp) : 191.2+/-2.5 kcal/mol Temperature ’ 300 K

Staley, R. H., Kleckner, J. E., and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used • ICR

Calculated entropy

Equilibrium relative to HC02Et, ME20 and EtCN

GB (exp) • 183.6+/-2 kcal/mol Temperature : 300 K

PA (exp) : 191.4+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
160

C4H8 CAS REGN : 106-98-9

C**C**C++C

1-Butene (8CI9CI)

PA (exp) • 183.2 kcal/mol Temperature : 298 K

Lossing F. P., and Semeluk, G. P. Free Radicals by Mass Spectrometry. XLII. Ionization

Potentials and Ionic Heats of Formation for C1-C4

Alkyl Radicals,

Can. J. Chetn. <+8, 955 ( 1970 ).

Method used • EM

Appearance potential of CAH9+ by EM
C4H8 j CAS REGH : 115-11-7

C**C**C

++

C

1-Propene, 2-methyl- (9CI)

Propene, 2-methyl- (8CI)

PA (exp) : 192.6+/-2 kcal/mol Temperature 363-553 K

Goren, A., and Munson, B. Thermochemistry of Alkyl Ions,

J. Phys. Chem. 80, 2848 (1976).

Method used ' MS

Usinq delta Hf(t~C4H9+) = 169+/-1.8 derived from,

delta Hf(t-C4H9) = 9.3 and IP(t-C4H9) = 159.9

| PA (exp) : 193.7 kcal/mol Temperature :

Lossing F. P., and Semeluk, G P . Free Radicals by Mass Spectrometry . XLII. Ionization

Potentials and Ionic Heats of Formation for C1-C4

Alkyl Radi cals.

Can. J. Chem. 48, 955 (1970).

Method used : EM

Appearance potential of C4H9+

Continued on next page
162

GB (exp) ‘ 177.4+/-2 kcal/mol Temperature ’ 600 K

PA (exp) •' 194.2+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.»

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 185.1+/-2 kcal/mol Temperature '• 300 K

PA (exp) : 193.5+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T.» Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ; ICR

Calculated entropy

Equilibrium; scale based on NH3
163

C4H8 CAS REGN : 590-18-1

C**C++C**C

2-Butene, (Z)- C8CI9CI)

PA (exp) : 181.9 kcal/mol Temperature : 298 K

Lossing F. P., and Semeluk, G P . Free Radicals by Mass Spectrometry. XLII. Ionization

Potentials and Ionic Heats of

Alkyl Radicals,

Can. J. Chem. A8, 955 (1970).

Formation for C1-C4

Method used • EM

Appearance potential of CAH9+
164

C4H8 | CAS REGN : 594-11-6

|

C

X X

X X CXXXXXC

X

X c

Cyclopropane, methyl- (8CI9CI)

PA ( exp

)

181+/-2 kcal/mol Temperature •

Chong, S. L., and Franklin, J. L.,

Heats of Formation of Protonated Cyclopropane,

Methylcyclopropane, and Ethane,

J. Am. Chem. Soc. 94, 6347 (1972).

Method used : MS

Equilibrium relative to HCOOH

based on P A ( HCOOH ) = 1 8 0 . 1 +/-2 assuming delta S = 0 Correction for path degeneracy.
165

C4H8 CAS REGN : 624-64-6

C*#C++C**C

2-Butene, (E)- (8CI9CI)

PA (exp) s 180.9 kcal/mol Temperature '• 298 K

Lossinq F. P., and Semeluk, G P. Free Radicals by Mass Spectrometry. XLII. Ionization

Potentials and Ionic Heats of

Alkyl Radi cals.

Can. J. Chem. 48, 955 (1970).

Formation for C1-C4

Method used ’• EM

Appearance potential of C4H9 +
166

C4H8F3N CAS REGN : 819-06-7

F

K#

C**N**C**C**F

* x

X X C F

Ethanamine, 2 , 2 , 2-tr i f luoro-N , N-di methyl- (9CI)

Ethylamine, 2 > 2 , 2~t r i f luo ro~N , N-d i methy 1 - C8CI)

GB (exp) ‘ 204.7+/-2 kcal/mol Temperature • 300 K

PA (exp) • 212.4+/-2 kcal/mol Temperature ; 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
167

C4H8F3N CAS REGN : 819-46-5

F

X

X Fxxc**C**C**C**N

X

XF •

1-Butanamine, 4,4,4-trifluoro- (9CI)

Butylamine, 4 , 4 , 4-tr i f luoro- (8CI)

GB (exp) • 203.9+/-2 kcal/mol Temperature • 300 K

PA (exp) : 212.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
168

| C4H8N2 CAS REGN : 926-64-7

| N#i.l C**C**N**C

X

XC

Acetonitrile, ( di methylami no )- (8CI9CI)

GB (exp) • 200.9+/-2 kcal/mol Temperature : 300 K

PA (exp) : 208.7+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver , Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
169

C4H80 CAS REGN : 78-84-2

C**C**C++0

#

C

Propanal, 2-methyl- (9CI)

Isobutyraldehyde (8CI)

GB (exp) : 182.8+/-2 kcal/mol Temperature : 300 K

PA (exp) : 190.6+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
170

C4H80 CAS REGN : 78-93-3

C*#C**C**C

++

0

2-Butanone (8CI9CI)

GB (exp) - 189.2+/-2 kcal/mol Temperature • 300 K

PA (exp) ' 197+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 193.7+/-1 kcal/mol Temperature : 293 K

Lossi ng, F . P

.

Heats of Formation of Some Isomeric tCnH2n + 10]+

Ions. Substitutional Effects on Ion Stability,

J. Am. Chem. Soc. 99, 7526 (1977).

Method used • EM

Electron impact fragmentation (various molecules)

using EM. delta Hf(H+) = 365.7
C4H80 CAS REGN : 109-99-9

CXKKK#0

X X X X C C

X X X X C

Furan, tetrahydro- (8CI9CI)

GB (exp) : 189+/-2 kcal/mol Temperature ; 300 K

PA (exp) ' 196.4+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
172

1

I C4H80

1

1 CAS REGN : 123-72-8

. 1 o++c**c**c**c

Butanal (9CI)

Butyraldehyde (8CI)

GB (exp) : 181.9+/-2 kcal/mol Temperature = 300 K

PA (exp) • 189.7+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I.» Tsagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
173

1

I C4H802

1 CAS REGN : 1 10-74-7

c**c**c**o**c++o

Formic acid, propyl ester (8CI9CI)

PA (exp) • 194+/-2 kcal/mol Temperature '• 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to CH2C0 AND I-C4H8;

scale based on NH3.

GB (exp) • 184.7+/-2 kcal/mol Temperature s 298 K

PA (exp) : 192.1+/-2 kcal/mol Temperature : 298 K

Harrison, A. G., Lin, P. H., and Tsang, C. W.,

Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry

,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used ‘ MS

Equilibrium; scale based on (CH3)2C0

Entropy change assumed zero Continued on next page
174

GB (exp) '• 184.5 kcal/mol Temperature : 300 K

PA (exp) : 192.3+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 176.1+/-2 kcal/mol Temperature ’• 600 K

PA (exp) : 191.7+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3
175

C4H802 CAS REGN : 123-91-1

o#*c

X X

X X c c

X X X X C#xo

1 , 4-Di oxane ( 9CI

)

p-Dioxane (8CI)

GB (exp) : 183.9+/-2 kcal/mol Temperature • 300 K

PA (exp) • 190.9+/-2 kcal/mol Temperature : 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ‘ ICR

Calculated entropy

Equilibrium; scale based on NH3
176

C4H802 CAS REGN : 141-78-6

c**c**o**c**c

+

+0

Acetic acid ethyl ester (8CI9CI)

PA (exp) : 197+/-2 kcal/mol Temperature : 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2A27 (1973).

Method used ' MS

Bracketing relative to (C2H5)20 and CH3C02ME.

GB (exp) • 188.6+/-2 kcal/mol Temperature • 300 K

PA (exp) : 196+/-2 kcal/mol Temperature : 300 K

Harrison, A. G., Lin, P. H., and Tsang, C. W.,

Proton Transfer Reactions by Trapped-Ion Mass

Spect romet ry

,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976)

Method used : MS

Equilibrium; scale based on (CH3)2C0

Entropy change assumed zero Continued on next page
177

GB (exp) • 190.3+/-2 kcal/mol Temperature • 300 K

PA (exp) : 198.1+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5A17 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 182.A+/-2 kcal/mol Temperature = 600 K

PA (exp) : 198+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on NH3
178

I

I C4H802

1 —

CAS REGH : 554-12-1

| CX*0**C**C**C

+

+

0

Propanoic acid, methyl ester (9CI)

1 Propionic acid, methyl ester (8CI)

GB (exp) : 189.8+/-2 kcal/mol Temperature : 300 K

I PA (exp) ; 197.6+/-2 kcal/mol Temperature s 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) • 197+/-2 kcal/mol Temperature : 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used ' MS

Bracketing relative to (C2H5)20 and CH3C00Me
179

| C 4 h’ 8 0 2

1 CAS REGN = 625-55-8

| 0++C*X0*XC**C

X

Xc

j Formic acid, 1 -methyl ethyl ester (9CI)

i Formic acid, isopropyl ester (3CI)

GB (exp) : 185.8+/-2 kcal/mol Temperature •' 298 K

PA (exp) • 193.2+/-2 kcal/mol Temperature • 298 K

Harrison, A. G., Lin, P. H., and Tsanq, C. W.,

Pro-ton Transfer Reactions by Trapped-Ion Mass

Spectrometry

,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used : MS

Equilibrium; scale based on (CH3)2C0

Entropy change assumed zero
180

C4H802S CAS REGN : 38103-96-7

C**0**C**S**C**C

++

0

Carbonothi o i c acid, S-ethyl 0-methyl ester (9CI)

GB (exp) : 190.5+/-2 kcal/mol Temperature • 300 K

PA (exp) : 198.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
181

1

I C4H803 CAS REGN : 623-53-0

L

i c**o**c*#o**c*xc

+

+ . 0

I Carbonic acid, ethyl methyl ester (8CI9CI)

| GB Cexp) : 192.1+/-2 kcal/mol Temperature : 300 K

' PA (exp) : 199.9+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel , Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
182

C4H9N | CAS REGM : 123-75-1

| C*x*x*N

x x x x C C

X X

X X C

Pyrrolidine C8CI9CI)

GB (exp) : 213.70+/-2 kcal/mol Temperature : 300 K

PA (exp) • 221.90+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel , Taagepera,

Mclver, Beauchamp, and Taft.

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 213.30+/-2 kcal/mol Temperature • 298 K

PA (exp) : 221.50+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
183

CAH9N j CAS REGN = 1190-79-0

C**C++N**C**C

Ethanamine, N~e thy 1 i dene- (9CI)

Ethy lami na , N-ethyl i dene- (8CI)

1

1

1 PA ( exp

)

220.5+/-2 kcal/mol

1

| Temperature :

1 Aue, D. H., Webb, H. M., and Bowers, M. T.,

Proton Affinities, Ionization Potentials, and

Hydrcqan Affinities of Nitroqon and Oxyqen Bases.

Hybr i di zat i on Effects,

J. Am. Chem. Soc. 97, 4137 (1975).

Method used = ICR

Equilibrium; scale based on CH3MM2
184

C4H9N0 CAS REGN : 1 10-91-8

o**c

* K X x C C

X x

X x C**N

Morpholine (8CI9CI)

GB (exp) • 208.6+/-2 kcal/mol Temperature : 298 K

PA (exp) : 216.8+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
185

I C4H9N0

- CAS REGN : 127-19-5

CxxC*xN**C

+ * + * 0 C

Acetami de. N , N-di methyl- (8CI9CI)

GB (exp) • 205.4+/-2.5 kcal/mol Temperature : 300 K

Taft, R. W.,

Proton-Transfer Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, Neu York, 1975) Ch. 2.

Method used : ICR

Equilibrium; scale based on NH3
186

CAH9N0 CAS REGN : 563-83-7

C**C**C%%N

* X

X %

C 0

Propanamide, 2-methyl- (9CI)

Isobutyrami de (8CI)

GB (exp) 5 206.1+/-2 kcal/mol Temperature : 300 K

PA (exp) • 213.9+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ICR

Calculated entropy

Equilibrium; scale based on NH3
CAH10 CAS REGN : 106-97-8

C**C**C**C

Butane (8CI9CI)

PA (exp) : 166.8 (2) kcal/mol T emperature 291 K

Hiraoka, K ., and Kebarle, P.,

Stabilities and Enerqetics of Pentacoordi nated

Carbonium Ions. The Isomeric C2H7+ Ions and Some

Higher Analogues: C3H9+ and CAH11+,

J. Am. Chem. Soc. 98, 6119 (1976).

Method used : MS

Van’t Hoff plot

C-H proto nation (2)

Equilibrium of reaction t~CAH9+ + H2 -> CAH11+ (2)

PA (exp) : 16A (1) kcal/mol T emperature 291 K

Hiraoka, K., and Kebarle, P.,

Stabilities and Enerqetics of Pentacoordi nated

Carbonium Ions. The Isomeric C2H7+ Ions and Some

Higher Analogues: C3H9+ and CAH11+,

J. Am. Chem. Soc. 98, 6119 (1976).

Method used : MS

Van't Hoff plot

C-C proto nation (1)

Equilibrium of reaction C3H7+ + CHA -> CAH11+ (1)
188

I C4H10N2

r

CAS REGN : 1 10-85-0

. N**C

X X

X X

1 C C

x x

x x C**N

Piperazine C8CI9CI)

GB (exp) : 210.9+/-2 kcal/mol Temperature : 298 K

1 PA (exp) : 218.9+/-2 kcal/mol Temperature : 298 K

Aue, D. H . , Webb, H. M., and Bowers, M. T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
189

C4H100 CAS REGN : 60-29-7

. c**c**o**c**c

Ethane, 1,1'-oxybis- (9CI)

Ethyl ether (8CI)

PA (exp) : 198+/-4 kcal/mol Temperature : 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxyqenated Compounds,

J. Am. Chem. Soc. 95, 2A27 (1973).

Method used : MS

Bracketing relative to (CH3)2C0 and NH3.

GB (exp) • 188.7+/-2 kcal/mol Temperature "• 300 K

PA (exp) : 196.1+/-2 kcal/mol Temperature : 300 K

Harrison, A. G., Lin, P. H., and Tsanq, C. l*J

.

, Proton Transfer Reactions by Trapped-Ion Mass

Spectrometry,

Int. J. Mass Spectrom. Ion Phys. 19, 23 (1976).

Method used •* MS

Equilibrium; scale based on (CH3)2C0

Entropy change assumed zero Continued on next page
190

GB (exp) = 182.5+/-2 kcal/mol Temperature : 600 K

PA (exp) : 197.3+/-2 kcal/mol Temperature : 600 K

Yamdaqni , R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 190+/-2 kcal/mol Temperature : 300 K

PA (exp) : 197.4+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.»

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
191

C4H10O

r

CAS REGN : 71-36-3

j Q**C**C**C**C

I 1-Butanol (9CI)

| Butyl alcohol (8CI)

C-B (exp) • 181.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 189.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
192

C'+H 1 0 0 CAS REGN : 75-65-0

0

XX CXXCXXC

X

XC

2-Propanol, 2-methyl- (9CI)

tert~Butyl alcohol (8CI)

PA (exp) *• 194+/-1 kcal/mol Temperature •

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to CH2C0 and I-C5H10

PA (exp) : 192 kcal/mol Temperature :

Hiraoka, K., and Kebarle, P. Condensation Reactions Involving Carbonium Ions and

Lewis Bases in the Gas Phase. Hydration of the

tert-Butyl Cation,

J. Am. Chem. Soc. 99, 360 (1977).

Method used '• MS

Equilibrium relative to known standard acids
193

C'+H 1 0 5

1 CAS REGN : 75-66-1

1

S

*X c#*c**c

X

Xc

2-Propanethi ol , 2-methyl- (8CI9CI)

GB (exp) • 186.8+/-2 kcal/mol Temperature • 300 K

PA (exp) : 194.6+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
194

C4H10S

I CAS REGN : 352-93-2

1 C*xcxxs**C**C

Ethane, 1 ,

1

1 -thi ob i 5- (9CI)

Ethyl sulfide (8CI)

GB (exp) : 195.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 202.6+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel , Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

tquilibrium; scale based on HH3
195

C4H 1 IN nCAS REGN * 75-64- 9

NX

X 1 C**C**C

X

XC

2-Propanami ne, 2-methyl- (9CI)

tert-Butylami ne (8CI)

GB (exp) : 210.4+/-2 kcal/mol T emperature : 300 K

PA (exp) : 218.8+/-2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used ’• ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 210.2+/-2 kcal/mol T emperature : 298 K

PA (exp) : 218.6+/-2 kcal/mol J

T emperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

f Potentials,

Method used ; MS

Calculated entropy

Equilibrium; scale based on CH3NH2
196

C4H 1 IN CAS REGN : 78-81-9

C**C**C**N

X

XC

1-Propanami ne, 2-methyl- (9CI)

I sobutylami ne (8CI)

GB (exp) • 207.7+/-2 kcal/mol Temperature : 298 K

Taft, R. W.,

Proton-T ransfer Reactions,

Ed, E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2

Method used : ICR

Equilibrium; scale based on NH3

GB (exp) • 208.3+/-2 kcal/mol Temperature : 298 K

PA (exp) : 216.7+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
197

C4H 1 IN rCAS REGN : 109-73 -9

N**C**C**C**C

1 -Butanami ne (9CI)

Buty lami ne (8CI )

GB C exp) : 207.6+/-2 kcal/mol Temperature : 300 K

PA (exp) : 216+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) ’ 207.8+/-2 kcal/mol Temperature : 298 K

PA (exp) • 216.2+/-2 kcal/mol Temperature * 298 K

Aue, D. H., Webb, H. M .

,

A Thermodynami c Analysis

Basicities of Alkylamines

of Substituent Effects,

J. Am. Chem. Soc. 98, 318

and Bowers , M . T .

,

of Solvation Effects on the

. An Electrostat i c Analysis

( 1976)

.

Method used •’ ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
198

1

I C4H 1 IN

1

1 CAS REGN : 109-89-7

' _______ ___ 1

| C**C**N**C**C

Ethanamine, N-ethyl- (9CI)

Diethylamine (8CI)

1 GB (exp) • 214.50+/-2 kcal/mol Temperature : 300 K

PA (exp) : 222.70+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 214.10+/-2 kcal/mol Temperature • 298 K

PA (exp) : 222.30+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potontials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
199

C4H1 IN r

CAS REGN : 598-56-1

C**N**C*#C

XC

Ethanamine, N> N~di methyl- (9CI)

Ethylamine, N , N-di methyl- (8CI)

G3 (exp) ' 216.70+/-2 kcal/mol T emperature : 300 K

PA (exp) • 224.50+/-2 kcal/mol T emperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 216.00+/-2 kcal/mol T emperature : 298 K

PA (exp) • 223.80+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

9 Potentials,

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
200

C4H 1 IN CAS REGN : 13952-84-6

c#*c**c**c

X

x

N

2-Butanami ne (9CI)

sec-Butylami ne (SCI)

GB (exp) : 208.9 kcal/mol T emperature 30 0 K

Taft, R. W.,

Proton-Transfer Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2.

Method used : ICR

Equilibrium; scale based on NH3

GB ( exp) 209.3+/-2 kcal/mol Temperature : 298 K

PA ( exp

)

217.7+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
1

1 C4H12N2

1 CAS REGN : 1 10-60-1

| N**C*XC**C**C**N

1 , 4-Butanedi ami ne (8CI9CI)

I GB (exp) ; 221.70+/-2 kcal/mol Temperature : 298 K

I PA (exp) '• 236.60 + /-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers. M . T.,

Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
202

C5 Fe05 | CAS REGN : 13463-40-6

0

#

#

c c##o

* K ** 0##C**FE*C##0

XXc

#

#

0

Iron carbonyl (Fe(C0)5), (TB-5-11)- (9CI)

Iron carbonyl (FeCC0)5) C8CI)

PA (exp) ' 200+/-3 kcal/mol T emperature 300 K

Foster, M. S., and Beauchamp, J. L.,

Gas-Phase Ion Chemistry of Iron Pentacarbonyl by

Ion Cyclotron Resonance Spectroscopy. New Insights

into the Properties and Reactions of Transition

Metal Complexes in the Absence of Complicating

Solvation Phenomena,

J. Am. Chem. Soc. 97, 4808 (1975).

Method used • ICR

Bracketing relative to (CH30)2C0 and NH3.
203

C5H3C1N4 CAS REGN : 87-42-3

N

CL*C

HZZZZZC

1H-Purine, 6-chloro- (9CI)

Purine, 6-chloro- (8CI)

PA (exp) • 207+/-5 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J . A. , Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used : MS

Bracketing relative to NH3 and CH3NH2.
204

C5H4C1N

• CAS REGN : 109-09-1

C

n’ C

CL*C c

c

Pyridine, 2-chloro- (8CI9CI)

GB (exp) '• 204.0+/-2 kcal/mol Temperature • 300 K

PA (exp) : 211.8+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
205

C5HAC1N CAS REGN : 626-60-8

N

c* ‘c

CL*C C

c"

Pyridine, 3-chloro- (8CI9CI

)

GB (exp) : 204.5+/-2 kcal/mol Temperature ‘ 300 K

PA (exp) : 212.3+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
206

C5H4C1N CAS REGN : 626-61-9

C

c* ’n

CL*C C V

Pyridine, 4-chloro- C8CI9CI)

GB (exp) *• 207.2 + /-2 kcal/mol Temperature : 300 K

PA (exp) ; 215+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
207

C5H4FN

r

CAS REGN : 372-47-A

N

c' C

F**C C

c*

Pyridine, 3-fluoro- (8CI9CI)

GB C exp ) : 203.7+/-2 kcal/mol Temperature ' 300 K

PA (exp) : 211.5+/-2 kca 1/mo 1 Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
208

C5H4FN CAS REGN : 372-48-5

N C

F**C C V

Pyridine, 2-fluoro- (8CI9CI)

GB (exp) : 200.6+/-2 kcal/mol Temperature : 300 K

PA (exp) : 208.4+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
209

C5H4FN

1 CAS REGN : 694-52-0

1

C

c’ N

F**C C V

Pyridine, 4-fluoro- (8CI9CI)

GB (exp) : 206.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 2H.2+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclvcr, Beauchamp, and Taft.

Method used s ICR

Calculated entropy

Equilibrium; scale based on NH3
210

C5H4N202 | CAS REGN s 1122-61-8

C

c'

* N

0++N**C C

+

+ . . 0 C

Pyridine, 4~nitro~ (8CI9CI)

GB (exp) : 198.4+/-2 kcal/mol Temperature : 300 K

PA (exp) : 206.2+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 201+/-2 kcal/mol Temperature : 300 K

Taagepera, M., Henderson, W. G., Brownlee, R. T. C.,

Beauchamp, J. L., Holtz, D., and Taft, R. W.,

Gas-Phase Basicities and Pyridine Substituent Effects.

J. Am. Chem. Soc. 94, 1369 (1972).

Method used • ICR

Equilibrium; scale based on Pyridine
211

C5H4N40 I CAS REGN : 68-94-0

| C

n' ’n

ozzc c

. %

. . %

C N

x %

K Z HZZZZZC

6H~Pur i n-6~one, 1,7-dihydro- (9CI)

Hypoxanthine (8CI)

PA (exp) : 215+/-4 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used '• MS

Bracketing relative to CH3NH2 and ( CH3 ) 2NH

.
212

C5H5N CAS REGN : 1 10-86-1

C. .N

o o

o o

-

Pyridine (8CI9CI)

GB (exp) : 210.3+/-2 keal/mol Temperature • 300 K

PA (exp) • 218.1+/-2 keal/mol Temperature • 300 K

Unpublished work by L'Jolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : >209.7 keal/mol Temperature : 423-473 K

Dzi di c , I .

,

Relative Gas-Phase Basicities of Some Ami nos,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used • MS

Bracketing relative to ( C H 3 ) 2 N H Continued on next page
213

GB (exp) • 209.8+/-2 kcal/mol Temperature : 298 K

PA (exp) • 217.6+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M.» and Bowers, M. T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

GB (exp) : 203.7+/-2 kcal/mol Temperature : 600 K

i PA (exp) : 220.9+/-'2 kcal/mol Temperature : 600 K

Brigqs, J. P., Yamdagni, R., and Kebarle, P.,

Intrinsic Basicities of Ammonia, Methyl am i nos

,

Anilines, and Pyridine from Gas-Phas Proton-Exchange

Equ i 1 i br i a

,

J. Am. Chem. Soc. 99, 5128 (1972).

Method used • MS

Equilibrium; scale based on Entropy change assumed zero

NH3
214

C5H5N5 CAS REGN : 73-24-5

[ C

n’ n

H'/.XC C

. %

. . %

C N

X %

* %

HXZZXZC

TH-Puri n-6-ami ne (9CI)

Adeni ne (8CI

)

PA (exp) • 220+/-2 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J . A . , Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used • MS

Bracketing relative to (CH3)2NH and (CH3)3N
215

C5H5N50 I CAS REGN : 73-40-5

CXXH

X X

X X X C . . N X

X

N**C CXXH

*C. .n’ %

%

0

6H-Puri n-6-one, 2~am i no- 1 , 7-d i hydro- (9CI)

Guanine (8CI)

PA (exp) ' 220+/-2 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J. A. , Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Aff i ni ty,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used : MS

Bracketing relative to (CH3)2NH and (CH3)3N.
C5H6N202 CAS REGN : 65-71-4 '

C. .N

c**c ‘czzo

"c.%. N

%

0

2,4( 1H,3H)-Pyrimidinedione, 5-methylThymine (SCI)

( 9CI

)

!

1

PA (exp) '• 207 + /-5 kcal/mol Temperature^

1 Wilson, M. S., and McCloskey, J . A. , Chemical Ion i rat i on Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chcm . 5oc. 97, 3436 (1975).

Method used : M5

Bracketing relative to NH3 and CH3NH2
217

I C5H7F302 I CAS R EGN : 383-66-4

F

xX F**C**C**0**C**C**C

X +

X +

F 0

Acetic acid, trifluoro-, propyl ester (8CI9CI)

GB ( exp

)

176.4+/-2 kcal/mol T emperature 300 K

PA (exp) 184.2+/-2 kcal/mol T emperature 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Cham. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
218

C5H8

. CAS REGN : 693-86-7

C

X X

X X C*xxx*c

X X C+ + C

Cyclopropane, ethonyl- (9CI)

Cyclopropane, vinyl- (8CI) I

GB (exp) '• 1S7.4+/-2 kcal/mol Temperature • 300 K

PA (exp) : 195.2+/-2 kcal/mol Temperature ' 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
219

C5H80

r

CAS REGN : 765-43 -5

C

• X *

X X CXXXXXC

X

X Cxxc

+

+0

Ethanone, 1-cyclopropyl- (9CI)

Ketone, cyclopropyl methyl (SCI)

GB (exp) : 194.4+/-2 kcal/mol T emperature : 300 K

PA (exp) : 202.2+/-2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taaqep era,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
220

C5H802 CAS REGN : 123-54-6

C**C**C**C**C

+ + + +

0 0

2 , 4-Pentanedi one (8CI9CI)

GB (exp) : 197.2+/-2 kcal/mol Temperature : 300 K

PA (exp) = 204.6+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. IJ . , Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water arid Ammonia From Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
221

C5H802 I CAS REGN : 2868-37-3

C

* X

X X CXXXXXC

X X Cxxoxxc

++

0

Cyclopropanecarboxyl i c acid, methyl ester (8CI9CI)

GB ( exp

)

192.3+/-2 kcal/mol T emperatu re 30 0 K

PA ( exp

)

200 . 1+/-2 kca 1/mo 1 T emperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepara,

Mclver, Beauchamp, and Taft.

Method u 5 e d : ICR

Calculated entropy

Equilibrium; scale based on NH3
222

C5H9N

i

I CAS REGN : 1 10-59-8

! 1 C**C**C**C**C#?<N

Pentaneni tri le (9CI)

Valeroni tr i le (SCI)

T 1

1 1

PA (exp) ' 191.9+/-2 kcal/mol Temperature : 300 K

1 1 Staley, R. H., Kleckner, J. E., and Beauchamp, J. L. Relationship between Orbital Ionization Energies

and Molecular Properties. Proton Affinities and

Photoelectron Spectra of Nitriles,

J. Am. Chem. Soc. 98, 2081 (1976).

Method used *• I CR

Calculated entropy

Equilibrium relative to HC02C2H5

G3 (exp) : 184.1+/-2 kcal/mol Temperature •' 300 K

PA (exp) • 191.9+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
223

C5H10

. CAS REGN : 513-35-9

C**C++C**C

*

C

2-Butene, 2-methyl- (SCI9CI)

PA (exp) = 194.4+/-2 kcal/mol Temperature : 363-553 K

Goren, A., and Munson, B. Thermochemi stry of Alkyl Ions,

J. Phys. Chem. SO, 28<+8 ( 1976 ).

Method used : MS

Van't Hoff plot

Equ i 1 i br i um of hydride transfer reaction between

(t~C4H9+) + Me2CHEt. This delta H of the reaction was determined from van't Hoff plot. PA CM) derived

from the obtained delta Hf(MH+); scale based on delta Hf(t-C4H9+) = 169
224

1

I C5H10

1 CAS REGN : 563-46-2

I c**c**c**c

+

+c

I 1-Butene, 2-methyl- (8CI9CI)

|

1 PA (exp) : 193.5+/-2 kcal/mol

1 Temperature • L_

Long, J., and Munson, B.,

Proton Affinities of Some Oxyqenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used • MS

Bracketing relative to Iso-C4H8

I PA (exp) : 197.32 kcal/mol Temperature : 300 K

Solomon, J. J., and Field, F. H. , Reversible Reactions of Gaseous Ions. IX. The

Stability of C4-C7 Tertiary Alkyl Carbonium Ions,

J. Am. Chem. Soc. 97, 2625 (1975).

Method used • MS

Equilibrium scale Based on delta H f ormat i on ( T-C4H9+

)

= 169 Kcal/mol

.

Continued on next page
225

GB not calculated for this reference

PA (exp) • 195.9+/-2 kcal/mol Temperature : 363-553 K

Goren, A., and Munson, B. Thermochemistry of Alkyl Ions,

J. Phys. Chem. 80, 28A8 (1976).

Method used ‘ MS

Equilibrium of hydride transfer reaction between

(t~C4H9+) + Me2CHEt. This delta H of the reaction was determined from van't Hoff plot. PA (M) derived

from the obtained delta Hf(MH+); scale based on delta Hf(t-C4K9+) = 169

C5H10O

r

CAS REGN : L

95-22-0

C**C**C**C**C

++

0

3-Pentanone (8CI9CI)

GB (exp) '• 191.1+/-2 kcal/mol T emperature : 30 0 K

PA (exp) • 198.5+/-2 kcal/mol Temperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taagepera

,

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
226

C5H 100

1 CAS REGN : 96-47-9

1 OXXXXXC

X X

X X CXXC C

X X X X C

Furan, tetrahydro~2-methyl- (8CI9CI)

GB (exp) • 192.5+/-2 kcal/mol Temperature • 300 K

PA (exp) : 200.3+/-2 kcal/mol Temperature ’ 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
227 -

C5H100 | CAS REGN : 110-62-3

c**c**c**c**c++o

Pentanal (9CI)

Valeraldehyde (8CI)

GB (exp) : 182.8+/-2 kcal/mol Temperature '• 300 K

PA (exp) : 190.6+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M .

,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5617 (1977).

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
228

C5H 1 00 CAS REGN : 192-68-7

C*xo

x x x x

C C

x x X X c**c

2H~Pyran, tetrahydro- (8CI9CI)

GB (exp) : 189.7+/-2 kcal/mol Temperature ; 300 K

PA (exp) 5 197.1+/-2 kcal/mol Temperature '• 30 0 K

Wolf, J. F„, Staley, R. H., Koppel, I., Taagepera, fl.,

Mclver, R. I., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J . Am. Chem. Soc. 99, 59 1 7 ( 1 977 ).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
229

C5H100 CAS REGN : 563-80-4

c**c**c**c

x +

x +

C 0

2-Butanone, 3-methyl- (8CI9CI)

GB (exp) s 190.8+/-2 kcal/mol T emperatu r

e

: 30 0 K

PA (exp) • 198.6+/-2 kcal/mol T emperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taagepera

,

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on NH3
230

C5H1002 | CAS REGN : 109-60-4

Cxxc**OX*C**C**C

+

+

Acetic acid, propyl ester (8CI9CI)

PA (exp) : 200+/-3 kcal/mol Temperature •

Long, J., and Munson, B.,

Proton Affinities of Some Oxyqenated Compounds,

J. Am. Chein. Soc. 95, 2427 ( 1973).

Method used MS

Bracketing relative to NH3 and CH3C00C2H5.

GB (exp) ; 182.9+/-2 kcal/mol Temperature • 600 K

PA (exp) : 200.1+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

Between Water and Ammonia and Substituted Benzenes from

A Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Equilibrium; scale based on NH3

Entropy change assumed zero
231

C5H1002

1 CAS REGN : 5A7-63-7

1 C*xo**C**C**C

+ x

+ X 0 C

Propanoic acid, 2-methyl-, methyl ester (9CI)

Isobutyric acid, methyl ester (8CI)

GB (exp) • 191.1+/-2 kcal/mol Temperature : 300 K

PA (exp) s 198.9+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
232

C5H10O2 | CAS REGN : 592-84-7

0 +

Formic acid, butyl ester (8CI9CI)

GB ( exp

)

: 134

.

7+/-2 keal/mol Temperature : 300 K

PA ( exp

)

: 192. 5+/-2 keal/mol Temperature : 300 K

Wolf, J M c I v e r ,. F. , R . T Staley, R. H., Koppel, I., Taaqepera, M.,

, Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Ilea su foment s

,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
233

C5H 1 IN r

CAS REGN : L_

1 10-89 -4

X C

X

C**N

X X X

C

X

X X Cxxc

Piperidine (8CI9CI

)

GB (exp) • 214.90+/-2 kcal/mol T emperature ' 300 K

PA (exp) '• 223.10+/-2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taagepera

,

!

i

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 214.40+/-2 kcal/mol T emperature : 298 K

PA (exp) ' 222.60+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydrogen Affinities of Alkylamines,

J. Am. Chein

.

Soc. 98, 3 1 1 ( 1976 ).

t Potentials,

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

Continued on next page
234

GB (exp) : 209.60+/-2 kcal/mol Temperature • 600 K

PA (exp) : 226.80+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha , omega-Di ami nes,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Equilibrium; scale based on NH3

Entropy change assumed zero

I C5H11N CAS REGN : 120-94-5

CxxxxxC

X X

X X

j CXXN C

X X

| X X C

Pyrrolidine, 1-methyl- (8CI9CI)

GB (exp) : 217.80+/-2 kcal/mol Temperature • 300 K

PA (exp) : 225.60+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
235

GB Cexp) : 217.30+/-2 kcal/mol T emperature : 298 K

PA (exp) : 225.10+/-2 kcal/mol T emperature •• 2 98 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Potentials,

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

C5H 1 1 N02 CAS REGN : 687-48

L_

-9

CXXN**C**0**C**C

x +

x +

C 0

Carbamic acid, dimethyl-, ethyl ester (8CI9CI)

GB (exp) : 203.4+/-2 kcal/mol Temperature ; 300 K

PA (exp) : 211.2+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel , Taagepera,

Mclver, Beauchamp, and Taft.

Method used * ICR

Calculated entropy

Equilibrium; scale based on NH3
236

1 C5H120 CAS REGN : 625-54-7

| C*XC**0**C**C

XX

C

Propane, 2-ethoxy- (9CI)

Ether, ethyl isopropyl (8CI)

GB (exp) : 192.9+/-2 kcal/mol Temperature : 300 K

PA (exp) ' 200.7+/-2 kcal/mol Temperature •' 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ICR

Calculated entropy

Equilibrium; scale based on NH3
237

C5H120

n

CAS REGN : 1634-04-4

C

XX C*XC**0X#C

X

x .

• c

Propane, 2-methoxy-2~methyl- (9CI)

Ether, tert~butyl methyl (8CI)

GB (exp) ' 191.7+/-2 kcal/mol T emperature : 30 0 K

PA (exp) • 199.5+/-2 kcal/mol T emperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on NH3
238

C5H13N | CAS REGN : 1 10-58-7

C**C**C#xC*xC**N

1-Pentanami ne C9CI)

Pentylamine (8CI)

GB (exp) : 208+/-2 kcal/mol Temperature • 298 K

PA (exp) • 216.4+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
239

C5H 1 3N CAS REGN : 594-39-8

N

*

X C*XC**C**C

XX

c

2-Butanami ne, 2-methyl- (9CI)

tert-Pentylami ne (8CI)

GB (exp) : 211.7+/-2 kcal/mol Temperature • 300 K

PA (exp) = 220.1+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Hclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 211.1+/-2 kcal/mol Temperature = 298 K

PA (exp) • 219.5+/-2 kcal/mol Temperature : 293 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
24 0

C5H 13N CAS REGH : 616-39-7

C**C**N**C**C

*C

Ethanamine, N-ethyl-N-methyl- (9CI)

D i ethyl am i ne , N-methyl- (8CI)

GB (exp) • 218.90+/-2 kcal/mol Temperature : 300 K

PA (exp) : 226.70+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 218.40+/-2 kcal/mol j Temperature s 298 K

PA (exp) : 226.20+/-2 kcal/mol | Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
C5H13N CAS REGN : 996-35-0

CxxcxxNxxC

X X

X X C C

2-Propanami ne, N , N~di methyl- (9CI)

Ethylamine, N , N ,

1 -t r i met hy 1 - (8CI)

GB (exp) '• 218.9+/-2 kcal/mol T emper a tu r

e

: 300 K

PA (exp) • 226.7+/~2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
242

C5H 13N

r

CAS REGN : 5813-64 -9

c 1 * 1 x j C**C*xCx*N j x 1 x | c 1

1-Propanami ne, 2,2-dimethyl- (9CI)

Neopentylami ne (8CI)

GB ( exp) • 208.8+/-2 kcal/mol T emperatu r

e

: 300 K

PA (exp) = 217.2+/-2 kcal/mol T emperatu re : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aaqepera

,

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 209.0+/-2 kcal/mol T emperatu re : 2 98 K

PA (exp) * 217.4+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydroqen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

f Potent i al s ,

Method used * ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
243

1

i C5H13N

1 CAS REGN : 19961-27-4

| C*#C**N**C**C

#

XC

I 2-Propanami ne, N-ethyl- (9CI)

j Diethylamine, 1 -methyl- (8CI)

| GB (exp) • 216+/-2 kcal/mol Temperature • 300 K

| PA (exp) : 224.2+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used * ICR

Calculated entropy

Equilibrium; scale based on NH3
C5H14N2

1

1 CAS REGN : 109-55-7

1

| C**N**C**C**C**N

X 1 Xc 1

1 , 3-Propanedi ami ne, N , N-d i methyl - C8CI9CI)

GB (exp) : 225 . 4+/-2 kcal/mol Temperature •' 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Equilibrium; scale based on NH3
245

C5H14N2 CAS REGH : 462-94-2

N*xcx*C*#C**C**CxxN

1 , 5-Pentanedi ami ne (8CI9CI)

GB (exp) : 220.00+/-2 kcal/mol Temperature ' 298 K

PA (exp) • 234.60+/-2 kcal/mol Temperature : 298 K

A u e , D. H . , Webb, H. M . , and Bowers, M . T . , Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

GB (exp) • 221.40+/-2 kcal/mol Temperature • 298 K

PA (exp) • 235.10+/-2 kcal/mol Temperature ; 298 K

Yamdagni , R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of a 1 pha , omega- D i am i nes

,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used • MS

Equilibrium; scale based on (CH3)3N

Van't Hoff plot
246

C6F6 CAS REGN : 392-56-3

F*xc

F F

x x

X X C. .C

C. .C

X X X X F F

C**F

Benzene, hexafluoro- (8CI9CI)

G3 (exp) : 171.2 kcal/mol Temperature • 373 K

PA (exp) : 178.5+/-2 kcal/mol Temperature = 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems 1 Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978)

Method used • ICR

Calculated entropy

Equilibrium; scale based on C6H6
247

C6HF5 CAS REGN : 363-72-4

C

F##C C**F

F**C C**F

VX

X

F

Benzene, pentafluoro- (8CI9CI)

GB (exp) : 172.7+/-2 kcal/mol Temperature • 373 K

PA (exp) : 180.3+/-2 kcal/mol Temperature : 373 K

Hartman, K. G., and Lias, S. ( Proton Transfer Equilibria in Halobenzene Systems:

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used : ICR

Calculated entropy

Equilibrium; scale based on C6H6
248

C6H2F4 CAS REGN : 327-54-8

C.

F

XX.C

F*XC CXXF

C.

X

XF

.c’

Benzene, 1 , 2 , 4 , 5-tetraf luoro- (8CI9CI)

GB (exp) • 173.1+/-2 kcal/mol Temperature '• 373 K

PA (exp) : 180.3+/-2 kcal/mol Temperature •* 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems : Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used : ICR

Calculated entropy

Equilibrium; scale based on C6H6
24 9

C6H2F4

r

CAS REGN : 551-62-2

1

1

C

F**C C

F**C C**F

V*

F

Benzene , 1 ,2,3,4-tetrafluoro- (8CI9CI)

GB (exp) • 173.4+/-2 kcal/mol Temperature • 373 K

PA (exp) • 180.4+/-2 kcal/mol Temperature • 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems 5 Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 23, 213 (1978).

Method used 5 ICR

Calculated entropy

Equilibrium; scale based on C6H6
250

I C6H2FA | CAS REGN : 2367-82-0

C

F**C C*#F

F**C C

C

x

xF

Benzene, 1 , 2 , 3 , 5-tetraf luoro- (8CI9CI)

I GB (exp) : 173.4+/-2 kcal/mol Temperature : 373 K

PA (exp) 180.5+/-2 kcal/mol Temperature : 373 K

Hartman, K. G., and Lias, S. ( Proton Transfer Equilibria in Halobenzene Systems:

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used : ICR

Calculated entropy

Equilibrium; scale based on C6H6
251

C6H3F3 CAS REGN : 367-23-7

L

o o

F**C C**F

*c. .c’

*

XF

Benzene, 1 , 2 , 4-tr i f 1 uoro- C8CI9CI)

GB Cexp) ’ 173.7+/-2 kcal/mol Temperature ’ 373 K

PA (exp) : 181.35+/-2 kcal/mol Temperature : 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems:

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used ; ICR

Calculated entropy

Equilibrium; scale based on C6H6
252

C6H3F3

• CAS REGN : 372-38-3

F

X

XC

c C

Fxxc C*XF

V

Benzene

,

1 , 3,5-tri fluoro- (8CI9CI)

G3 (exp) : 174.1+/-2 keal/mol Temperature • 373 K

PA (exp) : 181.15+/-2 keal/mol Temperature * 373 K

Hartman, K. G., and Lias, S. ( Proton Transfer Equilibria in Halobenzene Systems*

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 2 13 ( 1978) .

Method used •' ICR

Calculated entropy

Equilibrium; scale based on C6H6

Continued on next page
253

| GB (exp) J 165.4+/-2 kcal/mol Temperature : 600 K

| PA (exp) : 179.8+/-2 kcal/mol Temperature ; 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on NH3
254

C6H4F2 | CAS REGN : 367-11-3

C. .C

F**C C

*C. .C*

*

xF

Benzene, 1 , 2-di -fluoro- (9CI)

Benzene, o-difluoro- (8CI)

GB (exp) * 174.36+/-2 kcal/mol Temperature : 373 K

PA (exp) * 181.35+/-2 kcal/mol Temperature * 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems*

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used : ICR

Calculated entropy

Equilibrium; scale based on C6H6
255

C6H4F2 CAS REGN : 372-18-9

•o

o

•o

F**C C#*F

V

Benzene, 1 , 3 — d i f luoro- (9CI)

Benzene, m-difluoro- (8CI)

GB (exp) • 174.42+/-2 kcal/mol Temperature : 373 K

PA (exp) ’ 171.67+/-2 kcal/mol Temperature •' 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems-’

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used '• ICR

Calculated entropy

Equilibrium; scale based on C6H6

Continued on next page
256

GB (exp) • 165.9+/-2 kcal/mol Temperature : 600 K

j PA (exp) • 181.6+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.»

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Cham. Soc. 98, 1320 (1976).

Method used MS

Calculated entropy

Equilibrium; scale based on NH3
257

C6H4F2 CAS REGN : 5A0 -36 -3

C

c' C**F

F**C

* C

C

Benzene

,

1 , 4-di f luoro - ( 9CI

)

Benzene

,

p-di fluoro- ( 8CI )

GB (exp) : 173.9+/-2 kcal/mol Temperature : 373 K

PA (exp) : 180.6+/-2 kcal/mol Temperature '• 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems:

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used : ICR

Calculated entropy

Equilibrium; scale based on C6H6
258

C6H4F3N | CAS REGN : 368-48-9

C

F N’ C

x

x F**C**C C

x . X . . F C

Pyridine, 2- ( t r i f 1 uo romethy 1

) - (8CI9CI)

GB (exp) ' 201.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 209.0+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
259

C6H4F3N

r

CAS REGN : 3796-23-4

N

F C C

x

X FXXCXXC C

Xx . . . F C

Pyridine, 3- C t r i f 1 uo r ome-thy 1 ) - (8CI

)

GB (exp) • 202.2+/-2 kcal/mol Temperature : 300 K

PA (exp) • 210.0+/-2 kcal/mol Temperature : 300 K

1

1 Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
260

C6H4F3N CAS REGN : 3796-24-5

F C

x

x F#*C**C

xxF

Pyridine, 4- ( t r i f 1 uo romethy 1

) - (8CI9CI)

GB (exp) : 202.5+/-2 kcal/mol Temperature • 300 K

PA (exp) • 210.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

flclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 207.1+/-2 kcal/mol Temperature : 298 K

Taagepera, M., Henderson, W. ()., Brownlee, R. T. C.,

Beauchamp, J. L., Holtz, D., and Taft, R. W.,

Gas-Phase Basicities and Pyridine Substituent Effects,

J. Am. Chem. Soc. 94, 1369 (1972).

Method used = ICR

Equilibrium; scale based on C5H5N ( Py r i di ne

)
C6H4N2

C

C N

N##C**C C

*c’

j CAS REGN : 100-48-1

J

4-Pyr i di necarbon i tr i le (9CI)

Isoni coti noni tr i le (8CI)

GB (exp) • 199.8+/-2 kcal/mol Temperature • 30 0 K

PA (exp) • 207.6+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
262

| C6H9N2

1 CAS REGN : 100-59-9

N

C C

N##C**C C

c’

3-Pyri di necarboni tri le (9CI)

I Nicotinonitrile C8CI)

GB (exp) - 199.0+/-2 kcal/mol Temperature • 300 K

PA (exp) : 206.8+/-2 kcal/mol Temperature - 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
263

C6H4N2 CAS REGN : 100-70-9

L

C

n’ c

N##C**C C

c"

2-Pyri di necarboni tr i le (9CI)

Pi col i noni tri le (8CI)

GB (exp) : 197.8+/-2 kcal/mol Temperature ' 300 K

PA (exp) : 205.6+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
264

1

I C6H5C1

1 CAS REGH : 108-90-7

L

C

c' c

I CL*C C

c

Benzene, chloro- (8CI9CI)

GB (exp) : 174.24+/-2 kcal/mol Temperature : 373 K

PA (exp) • 181.9+/-2 kcal/mol Temperature • 373 K

Hartman, K. G., and Lias, S. G. Pro-ton Transfer Equilibria in Halobenzene Systems : Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used J ICR

Calculated entropy

Equilibrium; scale based on C6H6

Continued on next page
265

GB (exp) : 166.8+/-2 kcal/mol Temperature ; 600 K

PA (exp) J 182.5+/-2 kcal/mol Temperature • 600 K

Lau, Y. K., and Kebarle, P. Subst i tucnt Effects on -the Intrinsic Basicity of

Benzene 1 Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 98, 7452 (1976).

Method used : MS

Calculated entropy

Equilbrium relative to C6H6. Usinq GB and PA values

respectively 167.8+/-2 and 181.2 + /-2 kcal/tnol

GB (exp) : 166.8+/-2 kcal/mol Temperature : 600 K

| PA (exp) : 1S2.5+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3
266

1

I C6H5F

1

1 CAS REGN : 462-06-6

L.

C

c c

I F**c c

’c’

Benzene, fluoro- (8CI9CI)

GB (exp) * 174.5+/-2 kcal/mol Temperature * 373 K

PA (exp) : 182.2+/-2 kcal/mol Temperature * 373 K

Hartman, K. G., and Lias, S. G. Proton Transfer Equilibria in Halobenzene Systems*

Entropy Changes and Relative Proton Affinities,

Intern. J. Mass Spectrom. Ion Phys. 28, 213 (1978).

Method used * ICR

Calculated entropy

Equilibrium; scale based on C6H6

Continued on next page
267

GB (exp) : 167+/-2 kcal/mol Temperature • 600 K

PA (exp) s 182.5+/-2 kcal/mol Temperature • 600 K

Lau, Y. K., and Kebarle, P. Substituent Effects on the Intrinsic Basicity of

Benzene 1 Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 98, 7452 (1976).

Method used ’ MS

Calculated entropy

Equilibrium relative to C6H6. Usinq GB and PA values

respectively 167.8+/-2 and 181.2+/-2 kcal/mol

GB (exp) ' 166.9+/-2 kcal/mol Temperature : 600 K

PA (exp) : 182.6+/-2 kcal/mol Temperature s 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used * MS

Calculated entropy

Equilibrium; scale based on NH3
268

j C6H5N02 CAS REGN : 98-95-3

L_

C

c

’ c

| 0++N*xC c

+

+ . . 0 C

i Benzene, nitro- (8CI9CI)

j GB (exp) • 176.7+/-2 kcal/mol Temperature : 600 K

PA (exp) : 192.2+/-2 kcal/mol Temperature '• 600 K

Lau, Y. K., and Kebarle, P. Substituent Effects on the Intrinsic Basicity of

Benzene 1 Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 98, 7452 (1976).

Method used : MS

Calculated entropy

Equilibrium relative to C6H6. Using GB (C6H6) = 167.8+/-2 and PA (C6H6) = 181.2+/-2
269

C6H6

r

CAS REGN : 71-43- 2

C. .C

c' c

c. .c’

Benzene (8CI9CI)

GB (exp) s 172+/-2 kcal/mol T emperature : 340 K

PA (exp) : 180.1+/-2 kcal/mol T emperature : 340 K

Chong, S. L., and Franklin, J. L.,

Proton Affinities of Benzene, Toluene, and

J. Am. Chem. Soc. 94, 6630 (1972).

the Xylenes,

Method used MS

Equilibrium relative to HCOOH

Entropy change assumed zero

GB (exp) : 174.7+/-2 kcal/mol T emperatu re : 300 K

PA (exp) ' 181.4+/-2 kcal/mol T emperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M .

,

Mclver, R. T.» Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
270

GB (exp) • 167.8+/-2 kcal/mol Temperature : 600 K

PA (exp) : 181.2+/-2 kcal/mol Temperature • 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ' MS

Calculated entropy

Equilibrium; scale based on NH3
I

-27 1-

C6H6C1N I CAS REGN : 106-47-8

i

i

Benzenamine, 4-chloro- (9CI)

Aniline, p-chloro- (8CI)

GB (exp) : 198.5+/-2 kcal/tnol Temperature : 300 K

PA (exp) : 206.9+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqcpera,

Mclvar, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

C

c’ C**N

CL*C C

c’
272

I C6H6C1N | CAS REGN : 108-42-9

! I

C

c" c

I CL*C C**N

I

. -

i c

Ben renamine, 3-chloro- (9CI)

An i line, m-chloro- (SCI)

GB (exp) • 197.5+/-2 kcal/mol | Temperature

1

: 3 C 0 K

PA (exp) •' 205.9+/-2 kcal/mol | Temperature

1

•• 30 0 K

Unpublished work by Uolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taaqep era

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
273

C6H6FH CAS REGN : 371-A0-4

C

F**C

C**N

C

Benzenamine, 4-fluoro- (9CI)

Aniline, p-fluoro- (8CI)

GB ( exp) 198.0+/-2 kcal/mol Temperature 30 0 K

PA C exp

)

206 . A+/-2 kcal/mol T emperatu r

e

300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
274

1

I C6H6FN

1

1 CAS REGM : 372-19-0

C

•o•o

i

j F**C C**N

c'

1 Benzonamine, 3-fluoro- C9CI)

| Aniline, rrt-fluoro- (8CI)

G3 Cexp) : 197.0+/-2 kcal/mol Temperature : 300 K

PA (exp) : 205.4+/-2 kcal/mol Tem-perature ' 30 0 K

I Unpublished work by Wolf, Staley, Koppel , Taaqepera,

Mclver, Beauchamp, and Taf-t.

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
275

C6H6M4 I CAS REGH : 2004-03-7

C

n’ *N

C**C c

. %

. . %

C N

K Z

x % nzzzzzc

I IH-Purine, 6-methyl- (9CI)

I Purine, 6-methyl- (8CI)

I PA (exp) : 220+/-2 keal/mol Temperature :

Wilson, M. S., and McCloskey, J . A. , Chemical Ionization Mass Spcctrornotry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Aff i ni ty,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used •' MS

Bracketing relative to ( C H 3 ) 2 N H and (CH3)3N
276

C6H60 j CAS REG.N : 10S-95-2

C

c'

’ C

C**C C

c’

Phenol (8CI9CI)

.

PA (exp) ~ ISO kcal/mol Temperature •

DhFtggs, D. J. Mclver, R .. T., and Hehre, W. J. The Proton Affinities of Phenol,

J. Am. Chem. Soc. 99, 3853 (1977).

Method used • ICR

Bracketing relative to various molecules. Oxygen

protonati on

GB ( exp )

• 179. 1+/-2 kcal/mol

[ Temperature :

: 600 K

PA (exp) : 194.6+/-2 kcal/mol Temperature :

I 600 K

Lau, Y. K., and Kebarlo, P. Substituent Effects on the Intrinsic Basicity of

Benzcne : Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 93, 7452 (1976).

Method used : ICR

Calculated entropy

Equilibrium relative to C6H6. Using GB (C6H6) = 167.G+/-2 and PA (C6H6) = 181.2+/-2
277

I C6H60

1 CAS REGN = 6921-27-3

I CMC**C**0**C*XC##C

! 1-Propyne, 3,3'-oxybis- (9CI)

I 2-Propynyl ether (8CI)

1 GB (exp) ' 181.1+/-2 kcal/mol Temperature •' 3C0 K

| PA (exp) : 188.5+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
278

I C6H7N

1 CAS REGN : 62-53-3

1

C

j

c'

' c

! N**C c

c

1 Benzc-namine (9CI)

| Aniline (SCI)

I GB (exp) : 200.4+/-2 keal/mol Temperature : 300 K

PA (exp) : 203.8+/-2 keal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppol, Taagepera,

Mclver, Beauchamp, and Taft.

Hotbed used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB ( exp

)

193.4+/-2 k ca 1/tno 1 Temperature 6 0 0 K

PA ( exp

)

208 . 9+/-2 k ca 1/mo 1 T emperature 6 0 0 K

Lau, Y. K., and Kebarle, P. Substituent Effects on the Intrinsic Basicity of

Benzcne ; Proton Affinities of Substituted Benzenes,

J. Am. Chom. Soc. 98, 7452 (1976).

Method used : MS

Calculated entropy

Equilibrium relative to C6H6. Using GB (C6H6) - 167.3+/-2 and PA (C6H6) = 181.2

Continued on next page
279

GB (exp) •' >193.7 keal/mol Temperature • 423-473 K

Dzi die, I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 C1972).

! Method used : MS

i Bracketing relative to NH3

I GB (exp) ; 194.0+/-2 keal/mol Temperature : 600 K

) PA (exp) : 211.2+/-2 keal/mol Temperature : 600 K

Briggs, J. P., Yamdagni, R., and Kebarle, P.,

Intrinsic Basicities of Ammonia, Methylami nes. Anilines, and Pyridine from Gas-Phase ProtonExchange Equilibria,

J. Am. Chem. Soc. 94, 5128 (1972).

Method used • MS

Equilibrium; scale based on NH3

Entropy change assumed zero Continued on next page
280

GB (exp) : 199.9+/-2 kcal/mol Temperature : 298 K

PA (exp) ; 203.9+/-2 kcal/mol Temperature : 298 K

Aue, D. H . , Webb, H. M . , and Bowers, M . T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Cham. Soc. 98, 318 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
C6H7N

C N

C**C C

c

CAS REGN : 108-89-4

Pyridine, 4-methyl- (9CI)

4-Picoline (SCI)

GB (exp) : 214.30+/-2 kcal/mol T emperatu r

e

300 K

PA (exp) • 222.10+/-2 kcal/mol T emperatu re 300 K

Unpublished work by Wolf, Staley, Koppal, Taagepora,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
282

| C6H7N

1 CAS REGN : 108-99-6 |

1

N

•o•o

J c**c c

1 V 1

I Pyridine, 3-methyl- (9CI)

j 3-Picoline (SCI)

I GB (exp) : 213+/-2 kcal/mol Temperature : 300 K

PA (exp) • 220.8+/-2 kcal/mol

1

1 Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
283

| C6H7N

1 CAS REGH : 109-06-8

1

c

N

'

* C

I C**C C

; C

Pyridine, 2-methyl- C 9 C I

)

I 2-Pi coline (8CI)

I GB (exp) : 213.8+/-2 kcal/mol Temperature : 300 K

PA (exp) • 221.6+/-2 kcal/mol Temperature •* 30 0 K

Unpublished work by Wolf, Staley, Koppel, Taagcpera,

Mclver, Beauchamp, and Taft.

I Method used • ICR

1 Calculated entropy

Equilibrium; scale based on NH3
284

C6H7N | CAS REGN : 6921-28-4

Ctt£C**C**N**C**C#SC

2-Propyn- 1-smi no, N-2-propynyl - (9CI)

Di -2-propyny lain i ne (SCI)

GB (exp) 205.6+/-2 kcal/mol T emperature 300 K

PA ( exp

)

213.8+/-2 k ca 1/mo 1 T emperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scala based on NH3
285

C6H7N0 I CAS REGN : 620-08-6

I

C

c’ N

C**0**C c V

Pyridine, 4-methoxy- (8CI9CI)

GB (exp) : 217.00+/-2 kcal/mol Temperature : 300 K

PA (exp) • 22A.80+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
286

C6H7N0 | CAS RE6N : 694-85-9

C + + C

* x x x C**N C

x +

x + Cxxc

+

+

0

2(1rl)-PyridinonG, 1 -methyl- (9CI)

2 ( 1 H

) -pyr i done , 1-methyl- (SCI)

PA (exp) : 217.2+/-2 kcal/mol Temperature :

Cook, M. J., Katritzky, A. Singh, T. D., and Taft, R. Application o scopi c Gas-Pha

Tautomeric Equilibria,

J. Am. Chem. Soc. 98, 6048

R.U.

Taagepera, M

.

f Ion Cyclotron Resonance Spectroe Basicities to the Study of

( 1 976 ) .

Method used : ICR

Equilibrium relative to pyridine. Use value of

PA (pyridine) - 210.1

Entropy change assumed zero
287

1

1 C6H7N0

1

1 CAS REGN : 1628-89-3 1

1

i c

j N

'

* C

i c**0x*c c

! V

| Pyridine, 2-methoxy- (8CI9CI)

i GB (exp) : 211.4+/-2 kcal/mol Temperature •’ 300 K

| PA (exp) ' 219.2+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Eeauchamp, and Taft.

i Method used = ICR

| Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
288

PA (exp) : 219.8+/-2 kcal/mol Temperature :

Cock, M . J., Katritzky, A. R., Taaqepera, M . , Sinqh, T. D., and Taft, R. W. Application of Ion Cyclotron Resonance Spectroscopic Gas-Phase Basicities to the Study of

Tautomeric Equilibria,

J. Am. Chem. Soc. 98, 60A8 (1976).

Method used : ICR

Equilibrium relative to t-Butylami ne . Use value of

PA (t-CAH9NH2) = 218.3

Entropy change assumed zero
289

C6H7N0

nr CAS REGN : 7295^76-3

N

c’ C

C**0**C C

c*

Pyridine, 3~methoxy“ (8CI9CI

)

GB (exp) 213.3+/-2 kcal/mol Temperature : 300 K

PA (exp) 221. 1+/-2 kcal/mol Temperature ; 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
290

C6H7N50 | CAS REGN : 23662-75-1

C

K

K C%%N

% %

% %

% C. .N % . %

N**C CZXH

C. .N %

%

0

6 H-Pu r i n~6 -one , 2~ami no- 1 , 7 — d i hydro-8-methy 1- (9CI)

Guanine, 8-methyl- (8CI)

I

1

1 !

| PA (exp) >222 kcal/mol

1

I Temperature •

1

I Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used • MS

Bracketing relative to (CH3)3N
29 1

C6H8N2 CAS REGN : 95-54-5

C. .C

N**C* C

C..C

*K

N

1 , 2-Benzenedi am i ne C9CI)

o-Phenylenedi ami ne (SCI)

GB (exp) : >193.7 kcal/mol Temperature : 424-473 K

Dzi d i c , I .

/

Relative Gas-Phase Easiciti

Anilines, and Pyridines. An

Bronsted Acids as Reactants

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333

es of Some Amines,

Application of Some

in Chemical Ionization

( 1972) .

Method used • MS

Bracketing relative to NH3
292

C6H8N2 | CAS REGN : 106-50-3

C

c' C**N

N**C C

c

I 1 , 4-5enzened i am i ne (9CI)

I p-Phenyl enad i am i ns (8CI)

GB (exp) • >193.7 kcal/mol Temperature • 424-473 K

1

D z i d i c , I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Hass Spectrometry,

J. Am. Cham. Soc. 94, 8333 (1972).

Method used • MS

Bracketing relative to NH3
293

C6H3N2 CAS REGN : 108-45-2

C

c' c

N*#C C**N

*c’

1 , 3-Benzenedi ami ne (9CI)

m-Pheny 1 ened i am i ne (8CI)

GB (exp) • >202.9 kcal/mol Temperature : 424-473 K

Dz i d i c , I .

,

Relative Gas-Phase Basicities of Some Ami nos

,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used : MS

Bracketing relative to CH3NH2
294

C6H9F302 I CAS REGN i 367-64-6

F

X

X FXXC**C**0**C**C**C**C

x + x +

F 0

Acetic acid, trifluoro-, butyl ester (SCI9CI)

GB (exp) : 176.6+/-2 kcal/mol Temperature : 300 K

PA (exp) ; 184.4+/-2 kcal/mol Temperature •' 30 0 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
295

I C6H10

j

1 CAS REGN : 693-89-0 |

1

C x x x x x C

1 + X

1 + x

I C**C C

j X X

1 X X

I c

I Cyclopentene, 1-methyl- (8CI9CI)

| GB (exp) : 186.8+/-2 kcal/mol Temperature : 300 K j

I PA (exp) ' 195+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

! Hclver, Beauchamp, and Taft.

! Method used : ICR

> Calculated entropy

Equilibrium; scale based on NH3
296

I C6H10 . | CAS REGN : 1528-30-9

Cxxxxxc

x x

x x

I C++C c

x x

x x C

Cyclopentane, methylene- (8CI9CI)

GB (exp) " 190.7+/-2 kcal/mol Temperature : 298 K

Pollack, S. K., Wolf, J. F., Levi, B. A., Taft, R. W.,

and H e h r e W. J. Kinetic Detection of Common Intermediates in Gas

Phase Ion-Molecule Reactions,

J. Am. Chem. Soc. 99, 1350 (1977).

Method used : ICR

Equilibrium; scale based on NH3
297

C6H 10 CAS REGN : 4663-22-3

j

C

X X

X X CfcKKXXC

X

X C**C

+

C

Cyclopropane, (

1 -methyl ethenyl ) - (9CI)

Propeno, 2-cyclopropyl- (SCI)

GB (exp) > 198.9 + /-2 kcal/rnol Temperature '• 300 K

PA (exp) : 207.1+/-2 kcal/rnol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera, I Mclver, Beauchamp, and Taft.

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
298

C6H10F3NO I CAS REGS : 400-59-9

F

xx F**C**C%%N**C**C**C**C

* %

x %

F 0

Acetamide, N-butyl~2,2,2-trifluoro- (8CI9CI

)

G3 (exp) • 193.9+/-2 kcal/mol

1

I Temperature

1

: 300 K

PA (exp) : 201.7+/-2 kcal/mol

1

I Temperature

1

: 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taaqepera

,

Method used ; ICR

Calculated entropy

Equilibrium; scale based on NH3
C6H 100 | CAS REGN = 108-94-1

C

X X

X X C C

X X

X X

0 + + C C

x x X X

Cyclohexanone (3CI9CI)

PA (exp) 204 keal/mol Temperature :

Jelus, B. L., Murray, R. K., Jr., Munson, B.,

Studies in Chemical Ionization Mass Spectrometry.

Secondary Alcohols with Isobutane,

J. Am. Chom. Soc. 97, 2362 C1975).

Method used • MS

The (M~H)+ ion for eye 1 o~hexano 1 is assumed to

be the sane as O-protonated cyclohexanone.
300

1

i C6H10O

1

1 CAS REGN : 557-40-4

1 C++C**C**0**C*XC++C

i 1-Prcpene, 3,3’-oxybis- (9CI)

! Allyl ether (SCI)

i GB (exp) • 190+/-2 kcal/mol Temperature : 300 K

! PA (exp) ; 197.4+/-2 kcal/mol Temperature : 300 K

1 1 I 1 Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

i

C6H 1 IN | CAS REGN : 124-02-7

C++C**C**N**CK*C++C

2-Propen- 1-ami na, N-2-propeny 1- (9CI)

Di al lylarni ne (SCI)

GB ( exp

)

213.6+/-2 kcal/mol Temperature 300 K

PA ( exp

)

221.8+/-2 kcal/mol Temperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
C6H 1 1 NO

J

CAS REGN : 931-20-4

C**C

* X X X C**N C

X X X X CXXC

+

0

2-P i per i d i none , 1-methyl- (9CI)

2-P i per i done, 1-methyl- (8CI)

PA (exp) • 216.8+/-2 kcal/mol Temperature :

Cook, M. J., Katritzky, A. R., Taagepera, M., and

Singh, T. D.» and Taft, R. W.

Application of Ion Cyclotron Resonance Spectroscopic Gas-Phase Basicities to the Study of

Tautomeric Equilibria,

J. Am. Chem. Soc. 98, 6048 (1976).

Method used ’ ICR

Equilibrium relative to

PA (

i -C3H7NH2 ) = 216.5

Entropy change assumed

i -C3H7NH2 . Use value of zero
302

C6H 1 1 NO | CAS REGN = 53687-79-9

N

+ x C C

X 3$

'r. X CX*0***C C

X *

X X c

1 Piperidine, 2-methoxyPA (exp) : 226.3+/-2 keal/mol Temperature •

Cook, M. J., Katritzky, A. R., Taagepera, M., and

Sinqh, T. D., and Taft, R. W

.

Application of Ion Cyclotron Resonance Spectroscopic Gas-Phase Basicities to the Study of

Tautomeric Equilibria,

J. Am. Chem. Soc. 98, 6048 (1976).

| Method used : ICR

Equilibrium relative to (i-C3H7)2NH. Use value of

PA( i -C3H7 )2NH = 266.6

Entropy change assumed zero
303

C6H12 j CAS REGN : Not available

C

*

*C

X

X C#XC**C++C

1-Butene, 2-ethylPA (exp) : 197.7+/-2 kcal/mol T emperatu r

e

363-553 K

Goren, A., and Munson, B. Thermochemistry of Alkyl Ions,

J. Phys. Chem. 80, 2848 (1976).

Method used • MS

Equilibrium of hydride transfer reaction between

(t-C4H9+) + Et2CHMe and between (t-C5H11+) + Et2CHMe

.

This delta H of the reaction was determined from van’t

Hoff plot. PA (M) derived from the obtained delta Hf(MH+);

scale based on delta Hf(t~C4H9+) = 169
C6H 12 CAS REGN = 616-12-6

c**c++c**c**c

*

C

2-Pentene, 3-methyl-, (E)- (8CI9CI)

PA (exp) • 196.1+/-2 kcal/mol Temperature : 363-553 K

Goren, A., and Munson, B. Thormochcmi stry of Alkyl Ions,

J. Phys. Chem. 80, 2848 (1976).

Method used : MS

Equilibrium of hydride transfer reaction between

(t-C4H9+) + Et2CHMe and between (t-C5H11+) + Et2CHMe

.

This delta H of the reaction was determined from van't

Hoff plot. PA (M) derived from the obtained delta Hf(MH+);

scale based on delta Hf(t-C4H9+) - 169
305

C6H12 I CAS REGN : 625-27-4

C**C**C++C**C

X

Xc

2-Pentene, 2-methyl- (8CI9CI)

PA (exp) : 196.4+/-2 keal/mol Temperature • 363-553 K

Gorcn, A., and Munson, B. Thermochemistry of Alkyl Ions,

J. Phys. Chem. 80, 2848 (1976).

Method used : MS

Equilibrium of hydride transfer Reaction between

(t-C4H9+) + Me2CHC3H7 and between (t-C5H11+) + Me2Ch’C3H7. This delta H of the reaction was determined

from van't Hoff plot. PA (M) derived from the

obtained delta Hf(MH+); scale based on delta Hf(t~C4H9+) - 169
306

I C6H12 | CAS REGN : 763-29-1

| C**C**C**C**C

1-Penfcene, 2-methyl- (8CI9CI)

PA (exp) : 198.2+/-2 kcal/mol T emperatur

e

363-553 K

Goren, A., and Munson, B. Thermochcni siiry of Alkyl Ions,

J. Phys. Chem. 80, 2848 (1976).

Method used : MS

Equilibrium of hydride transfer reaction between

( t-CAH 9+ ) + Me2CHC3H7 and between (t-C5H11 + ) + Me2 CHC3H7. This delta H of the reaction was determined from

van’t Hoff plot. PA (M) derived from the obtained

delta Hf (MH+ ) ; scale based on delta Hf(t-C4H9+) = 169
307

C6H12N2 I CAS REGN : 280-57-9

C**N

X XX

X C X C * C

x c x xx x N*xc

1 ,4-Diazabicyclo[2.2.21octane C8CI9CI)

GB (exp) • 217.20+/-2 kcal/mol Temperature •

Taft, R. W.,

Proton-Trsnsfer Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2.

Method used : ICR

Equilibrium; scale based on NH3

GB (exp) ' 217.90+/-2 kcal/mol Temperature • 298 K

PA (exp) • 225.90+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

Continued on next page
308

PA (exp) : 225.50+/-2 kcal/mol Temperature :

Staley, R., and Beauchamp, J. Relationship of Nitrogen Lone

L. , Pair Interactions

to Thermodynamic Parameters Associated with Amine

Basicities,

I J. Am. Chem. Soc. 96, 1604 (1974).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

C6H120 | CAS REGN : 75-97-8

X

x C**C**C**C

x +

x + C 0

2-Eutanone, 3,3-dimethyl- (8CI9CI)

GB ( exp

)

19 1 . 8+/~2 kcal/mol

~r

| Temperature 3 0 0 K

PA (exp) 199.6+/-2 kcal/mol

~T~

| Temperature

1 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
309

C6H1202 CAS REGN : 598-98-1

C

*

X C*KO#XC**C**C

+ X + X 0 c

Propanoic acid, 2 , 2 — d i methyl- , methyl ester (9CI)

Pivalic acid, methyl ester (8CI)

GB (exp) : 192.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 200+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
310

C6H13N

1

| CAS REGN : 108-91-8

C

x x

X X C C

K X

X X N**C C

X X X X C

Cyclo'nexanam i ne (9CI)

Cyc 1 ohexy 1 am i ne (8CI)

G3 (exp) ; 210. 10+/-2 kcal/mol Temperature : 300 K

PA (exp) : 218.5+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamo, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 210.1+/-2 kcal/mol Temperature : 298 K

PA (exp) : 218.5+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Ulebb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydroqen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3HH2

Continued on next paqe
311

GB (exp) : 204.8+/-2 kcal/mol Temperature • 600 K

PA (exp) • 222+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of a 1 pha , omeqa- D i am i nes

,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Equilibrium; scale based on NH3

Entropy change assumed zero

C6H13N CAS REGN : 626-67-5

L_

C

* *

X X C C

X X

X X C**N C

X X X X C

Piperidine, 1-methyl- (8CI9CI)

GB (exp) = 218.8+/-2 kcal/mol Temperature : 300 K

PA (exp) • 226.6+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
3 12

GB (exp) • 218.3+/-2 keal/mol Temperature : 298 K

PA (exp) 5 226.1+/-2 keal/mol Temperature • 293 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylami nes,

I J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

1

| C6H1A0

1 r

CAS REGN = 108-20-3

X X X X c c

Propane, 2,2'-oxybis- (9CI)

I Isopropyl ether (SCI)

GB (exp) : 195.6+/-2 keal/mol Temperature : 300 K

PA (exp) • 203+/-2 keal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
313

C6H 1 40 CAS REGN : 1 1 1-43-3

C**C**C**0**C**C**C

Propane, 1,1’-oxybis- (9CI)

Propyl ether (SCI)

GB (exp) : 191.9+/-2 kcal/mol Temperature : 300 K

PA (exp) • 199.3+/-2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taagepera

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
3U

! C6H 1 40

1

1 CAS REGN : 637-92-3 | L_

c

• *

j c**c**o**c**c

j KXC

1

1 Propane, 2-ethoxy-2~methy 1 - (9CI)

j Ether, tert-butyl ethyl (SCI)

i GB (exp) : 195.5+/-2 kcal/mol

1

1 Temperature : 300 K

PA (exp) : 203.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
315

C6H14S

. CAS REGN = 111-47-7

C**C*XCx*S**C**C**C

Propane, 1 ,

1 ’ -thi obi s~ (9CI)

Propyl sulfide (8CI)

GB (exp) ’ 196.6+/-2 kcal/mol Temperature '• 300 K

PA (exp) : 204+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
3 16

C6H14S | CAS REGN : 625-80-9

C**C**S**C**C

x x x x C C

Propane, 2 , 2 ' -th i obi s- C9CI)

Isopropyl sulfide (SCI)

GB (exp) • 199.5+/-2 kcal/rnol T emperat ure 300 K

PA (exp) = 206.9+/-2 kcal/rnol T eitipera tu re 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taf-c.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
317

C6H15N | CAS REGN : 108-18-9

C**C**N**C**C

x x x x C C

2-Propanami ne, N-( 1-methylethyl )- (9CI)

Di i sopropylami ne C8CI)

GB ( exp

)

: 218.40+/-2 kcal/mol Temperature 300 K

PA ( exp

)

: 226.6 0+/-2 kcal/mol Temperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mcl ver , Beauchamp, and Taft.

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 217.90+/-2 kcal/mol Temperature : 298 K

PA (exp) • 226.1+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

A Thermodynami c Analysis of Solvation Effects on the

Basicities of Alkylamines. An El ec t ro sta t i c Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
318

C6H 15N CAS REGN : 1 1 1-26-2

• N*XC**C**C**C**C*XC

1-Hexanamine (9CI)

Hexyl amine (SCI)

G3 (exp) : 2C8.1+/-2 kcal/mol Temperature : 293 K

PA (exp) : 216.5+/-2 kcal/mol Temperature • 293 K

Aug, D. H., Webb, H. M . , and Bowers, M. T.,

Quant i tab i ve Evaluation of Intramolecular Strong

Hydroqcn Bondi na in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
319

C6H15N CAS REGN : 121-44-8

C**C**N**C**C

*

XC

K

*C

Ethanamine, N,N-diethyl~ (9CI)

Tr i ethylami ne (8CI)

GB (exp) • 221.20+/-2 kcal/mol Temperature : 300 K

PA (exp) s 229.00+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 220.60+/-2 kcal/mol Temperature • 298 K

PA (exp) • 228.40+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostatic Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
320

C6H 15N CAS REGN : 1A2-8A -7

1

!

1

1 Cxxcxxc**N**C**Cx*c

I 1-Propanami ne, H -propyl- (9CI)

Di propyl ami na CSC-I)

1 GB (exp) : 216.50+/-2 kcal/mol T emperature : 300 K

!

!

i PA (exp) • 22A.70+/-2 kcal/mol T emperature : 300 K

1

1

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepara

,

1

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 216.10+/-2 kcal/mol T emperature : 298 K

PA (exp) '• 224.30+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M.,

Quantitative Proton Affin

and Hydrogen Affinities o J. Am. Chem. Soc. 98, 311

and Bowers, M. T. ities, Ionization

f Alkylamines,

(1976).

f Potentials, I

1

Method used '• ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
C6H 15N

1 CAS REGN : 918-02-5

L_

CX

X Cxxc**N**C

X X

X X C C

2~P ropanam i ne , N , N , 2~t r i methyl - (9CI)

Et hy 1 am i ne , N , N , 1 ,

1 -tetramethyl- (8CI)

GB (exp) 5 220.6+/-2 kcal/mol Temperature : 300 K

PA (exp) : 228.A+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclvsr, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
322

j C6H16N2 | CAS REGN : 110-18-9

j C**N**C**C**N**C

x x * X C C

1 , 2-Ethanedi ami ne, N , N , N

’ , N ' -tetramethyl- (9CI)

i Ethylenedi ami ne, N > N , N

’ , N ' -tetramethyl- (8CI)

GB (exp) : 22A.6+/-2 keal/mol Temperature : 300 K

PA (exp) : 232.A+/-2 keal/mol Temperature ; 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

M elver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 224+/-2 keal/mol Temperature : 298 K

Taft, R. W.,

Proton-T ransf er Reactions,

Ed. E. F. Caldin and V. Gold,

(John Wiley and Sons, New York, 1975) Ch. 2.

Method used : ICR

Equilibrium; scale based on NH3
323

C6H16N2 CAS REGN *• 124-09--4

N**C**C**C**C**C**C**N

1,6 -Hexanedi ami ne (8CI9CI)

GB (exp) ' 220.00+/-2 kcal/mol Temperature •' 2 98 K

PA (exp) : 235.40+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

GB (exp) • 221.20+/-2 kcal/mol Temperature : 298 K

PA (exp) : 235.00+/-2 kcal/mol Temperature : 298 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton- Induced

Cyclization of alpha , omega-Di ami nes,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Equilibrium; scale based on Van't Hoff plot

( CH3 ) 3N
324

1

| C6H 17NS

i

1

1 CAS REGN : 18182-40-6

C

*

K

1 C**N**C**SI*C

* * * * C C

i

l

| Methanamine, N , N~d i methyl - 1 -( t r i methyl s i lyl ) - (9CI)

j Tr i methy lam i ne , ( t r i methyl 5 i lyl ) - (8CI)

G5 (exp) : 219.9+/-2 kcal/mol Temperature : 300 K

PA (exp) : 227.7+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
325

C7H5C10 CAS REGN : 1 0 4-88-

1

C

c’

* C**CL

o++c**c c V

Benzaldehyde, 4-chloro- (9CI)

Benzaldehyde, p-chloro- (8CI)

GB Cexp) • 189.8+/-2 kcal/mol T emperature : 300 K

PA (exp) ’ 197.6+/-2 kcal/mol Temperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taagepera

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
326

C7H5D3 | CAS REGN : 1124- IS1

C D

. . *

| . . *

j C C#*C**D

I . *

*

! C CD

Benzene* methyl-d3 -

GB (exp) : 180.9+/-2 kcal/mol Temperature : 300 K

PA (exp) : 188.7+/-2 kcal/mol Temperature : 300 K

Ausloos, P., and Lias, S. G. Equilibrium Isotope Effects on the Proton Transfer

Reactions of Methylbenzenes,

J. Am. Chem. Soc. 99, 4 1 93 ( 1977 ).

Method used •' ICR

Calculated entropy

Equilibrium; scale based on NH3
327

C7H5F0 CAS REGN : 456-48-4

C C

0++C#*C C#*F

V

Benzaldehyde, 3-fluoro- (9CI)

Benzaldehyde, m-fluoro- C8CI)

GB (exp) : 186.3+/-2 kcal/mol Temperature : 300 K

PA (exp) • 194.1+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
328

C7H5F0 | CAS REGN : 459-57-4

I C

C C**F

G++C**C C V

i Benzaidehyde , 4-fluoro- (9CI)

I Benzaidehyde, p-fluoro- (SCI)

GB (exp) • 183.9+/-2 kcal/mol Temperature : 300 K

PA (exp) : 196.7+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Nclver, Beauchamp, and Taft.

Method used ‘ ICR

Calculated entropy

Equilibrium; scale based on NM3
329

C7H5N CAS REGN * 100-A7-0

C

C* C

N##C**C C V

Benzonitrile (8CI9CI)

GB ( exp) 179.2+/-2 kcal/mol Temperature : 600 K

PA (exp) 19A.7+/-2 kcal/mol Temperature : 600 K

Lau, Y. K., and Kebarle, P. Substituent Effects on the Intrinsic Basicity of

Benzene 1 Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 98, 7A52 (1976).

Method used : MS

Calculated entropy

Equilibrium relative to C6H6. Using GB (C6H6) = 167.8+/-2 and PA (C6H6) = 181.2+/-2
330

1

\ C7H60

1

1 CAS REGN : 100-52-7

C

•o•o

I o++c**c c

1 V i

1

1 Benzaldehyde (8CI9CI)

1

I GB (exp) : 190.4 kcal/mol

\

1 ...... Temperature : 300 K

| PA (exp) : 193.2 kcal/mol Temperature : 300 K

i Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 183.2+/-2 kcal/mol Temperature : 600 K

PA (exp) • 193.7+/-2 kcal/mol Temperature : 600 K

Lau, Y. K., and Kebarle, P. Substituent Effects on the Intrinsic Basicity of

Benzene 1 Proton Affinities of Substituted Benzenes,

J. Am. Cham. Soc. 93, 7452 (1976).

Method used : MS

Calculated entropy

Equilibrium relative to C6H6. Using GB (C6H6) = 167.8+/-2 and PA (C6H6) = 181.2+/-2
331

C7H7N0 CAS REGN : 350-03-8

N

c* 'c

c*#c**c c

++ . . 0 c

Ethanone, 1 - C 3-pyr i d i ny 1

) - (9CI)

Ketone, methyl 3-pyridyl (8CI)

GB (exp) : 206.6+/-2 kcal/mol Temperature : 300 K

PA (exp) • 214.4+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
332

C7H7N0 CAS REGN : 1 122-5A-9

C

c’

’ N

| C**C**C C

i ++ . . o c

;

i Ethanone, 1 - ( 4-py r i d i ny 1

) - (9CI)

i Ketone, methyl 4-pyridyl (8CI)

I G3 (exp) : 206.8+/-2 kcal/inol Temperature : 300 K

PA (exp) • 214.6+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppol , Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
333

C7H8 CAS REGN : 108-88-3

C

c' ‘c

C**C C V

Benzene, methyl- (9CI)

Toluene (8CI)

GB (exp) • 179.6+/-2 kcal/mol Temperature : 340 K

PA (exp) : 137.5+/-2 kcal/mol Temperature : 340 K

Chong, S. L., and Franklin, J. L.,

Proton Affinities of Benzene, Toluene, and the Xylenes,

J. Am. Chem. Soc. 94, 6630 (1972).

Method used : MS

Equilibrium relative to CH3SH

Entropy change assumed zero

PA (exp) : 187.4+/-2 kcal/mol Temperature • 300 K

Devlin, J. L., III., Wolf, J. F., Taft, R. W.,

Hehre, W . J .

,

The Proton Affinities of Toluene,

J. Am. Chem. Soc. 98, 1990 (1976).

Method used • ICR

Equilibrium relative to C6H6 C Benzene)

Protonation position 2 Continued on next page
334

PA (exp) - 183.8+/-2 kcal/mol Temperature • 300 K

Devlin, J. L., III., Wolf, J. F., Taft, R. W.,

Hehr e , W . J .

,

The Proton Affinities of Toluene,

J. Am. Chem. Soc. 98, 1990 (1976).

Method used : ICR

Equilibrium relative to C6H6 ( Benzene)

Protonation position 3

PA (exp) : 182.6+/-2 kcal/mol Temperature : 300 K

Devlin, J. L., III., Wolf, J. F., Taft, R. W.,

Hehr e , W . J . , The Proton Affinities of Toluene,

J. Am. Chem. Soc. 93, 1990 (1976).

Method used ' ICR

Equilibrium relative to C6H6 ( Benzene

)

Protonation position 1

GB ( exp

)

174.1+/-2 kcal/mol T emperature 600 K

PA ( exp

)

139.6+/-2 kcal/mol T emperature 600 K

Lau, Y. K., and Kebarle, P. Substituent Effects on the Intrinsic Basicity of

Benzene^ Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 93, 7452 (1976).

Method used : MS

Calculated entropy

Equilibrium relative to C6H6. Usinq GB and PA values

respectively 167.3 + /-2 and 181.2+/-2 J<cal/mol

Continued on next page
335

GB (exp) • 180.8+/-2 kcal/mol Temperature • 300 K

PA (exp) • 188.6+/-2 kcal/mol Temperature • 300 K

Devlin, J. L., III., Wolf, J. F., Taft, R. W.,

Hehre , U) . J . , The Pro-ton Affinities of Toluene,

J. Am. Chem. Soc. 93, 1990 (1976).

Method used • ICR

Protonation position A Calculated entropy

Equilibrium relative to C6H6 ( Benzene)

GB (exp) • 180.9+/-2 kcal/mol Temperature •' 300 K

PA (exp) • 188.7+/-2 kcal/mol Temperature • 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5A17 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
336

GB (exp) 180.1+/-2 keal/mol Temperature • 300 K

PA ( exp

)

187.9+/-2 keal/mol Temperature : 300 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

I Measurements,

i J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on C6H6 ( Benzene)
337

C7H80 I CAS REGN * 100-66-3

C

c' ’c

c**o**c c V

Benzene, methoxy- (9CI)

Ani sole (8CI)

GB ( exp

)

183.5+/-2 kcal/mol Temperature : 60 0 K

PA (exp) 199+/-2 kcal/mol Temperature ’ 6 0 0 K

Lau, Y. K., and Kebarle, P. Subst i tuent Effects on the Intrinsic Basicity of

Benzene^ Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 98, 7452 (1976).

Method used : MS

Calculated entropy . Equilibrium relative to C6H6. Using GB (C6H6) = 167.8+/-2 and PA (C6H6) = 181.2+/-2
338

1

I C7H9N

1

I CAS REGN : 100-A6-9

1

C

c’ c

1 N**C**C C

c"

1 Benzenemethanam i ne (9CI)

I Benzyi amine (SCI)

i GB (exp) • 206.1+/-2 keal/mol Temperature : 300 K

I PA (exp) : 21A.5+/-2 keal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
339

C7H9N ' CAS REGN : 100-61-8

L

C

•o•o

C**N**C C V

Benzenamine, N-methyl- (9CI)

Aniline, N-methyl- (8CI)

GB (exp) : 200.2+/-2 kcal/mol Temperature •' 600 K

PA (exp) : 217.4+/-2 kcal/mol Temperature : 600 K

Briggs, J. P., Yamdagni, R., and Kebarle, P.,

Intrinsic Basicities of Ammonia, Methylami nes. Anilines, and Pyridine from Gas-Phase ProtonExchange Equilibria,

J. Am. Chem. Soc. 94, 5128 (1972).

Method used ’ MS

Equilibrium; scale based on NH3

Entropy change assumed zero
34 0

| C7H9N

C

| CAS REGN : 106-49-0

i

I c’ 'c**N

!

i

! c**c c

5

c'

Beneenami

p-Tc lu i d

i

ne, 4-methyl- (9CI)

ne ( 8CI

)

GB (exp) : 203.2+/-2 kcal/mol T emperature 300 K

PA ( exp

)

: 211.6+/-2 kcal/mol Temperature 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

I Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C7H9N CAS REGN : 108-44-1

C

c’ c

C**C C**N

V

Benzenamine, 3-methyl- (9CI)

m-Toluidine (8CI)

GB (exp) • 203.2+/-2 kcal/mol Temperature ' 300 K

PA (exp) • 211.6+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) : 211.6+/-2 kcal/mol Temperature : 298 K

Pollack, S. K., Devlin,

Taft, R. W., and Hehre,

J. L. U J. III, Summerhays, K. D.,

The Site of Protonation in Aniline,

J. Am. Chem. Soc. 99, 4583 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3. Ring protonation

Continued on next page
342

PA (exp) •" 211.6+/-2 kcal/mol Temperature : 300 K

Summerhays, K. D., Pollack, S

H e h r e , U . J . Gas-Phase Basicities of Substi

K., Taft, R. W., and

tuted Anilines.

Inferences about -the Role of Solvent in Dictating Site

of Protonation,

J. Am. Chem. Soc. 99, 4585 (1977).

Method used •' ICR

Calculated entropy

Equilibrium; scale base on NH3. Ring protonation
343

C7H9N CAS REGN : 108-47-4

C

c' 'n

c#*c c**c

*c’

Pyridine, 2,4-dimethyl- (9CI)

2,4-Lutidine (8CI)

PA (exp) ’ 225.1+/-2 kcal/mol Temperature • 298 K

Aue, D. H., Webb, H. M., Bowers, M. T., Liotta, C. L, Alexander, C. J., and Hopkins, H. P., Jr.

A Quantitative Comparison of Gas- and Solution-Phase

Basicities of Substituted Pyridines,

J. Am. Chem. Soc. 98, 854 (1976).

Method used ' ICR

Calculated Entropy

Equilibrium; scale based on NH3
C7H9N | CAS REGN : 103-48-5

C

c’ *c

.

j c**c c**c

i . .

I N

Pyridine, 2,6-dimethyl- (9CI)

2,6-Lutidine (8CI)

PA (exp) • 226.1+/-2 kcal/mol T emperature 298 K

Aue, D. H., Webb, H. M., Bowers, M. T., Liotta, C. L.,

Alexander, C. J., and Hopkins, H. P., Jr.

A Quantitative Comparison of Gas- and Solution-Phase

Basicities of Substituted Pyridines,

J. Am. Chem. Soc. 98, 854 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
345

I C7H9N | CAS REGN : 589-93-5

I

N

C C**C

C**C C

c’

Pyridine, 2 , 5 — d i methy 1- (9CI)

2,5-Lutidine (8CI)

PA (exp) : 224.5+/-2 kcal/mol Temperature ' 298 K

Aue, D. H.» Webb, H. M., Bowers, M. T., Liotta, C. L.,

Alexander, C. J., and Hopkins, H. P., Jr.

A Quantitative Comparison of Gas- and Solution-Phase

Basicities of Substituted Pyridines,

J. Am. Chem. Soc. 98, 854 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
346

C7H9N | CAS REGN : 591-22-0

C

C * a c c**c

! Pyridine, 3,5-dimethyl- (9CI)

i 3,5-Lutidine (SCI)

PA (exp) : 223.5 kcal/mol T emperature 298 K

Aue, D. H., Webb, H. M . » Bowers, M . T., L i o 1 1 a , C. L.,

Alexander, C. J., and Hopkins, H. P., Jr.

A Quantitative Comparison of Gas- and Solution-Phase

Basicities of Substituted Pyridines,

J. Am. Chem. Soc. 93, S54 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
347

C7H9N0 CAS REGN : 90-04-0

•o

o

•o

C*xo**C C V*

*N

Benzenami ne> 2-methoxy- C9CI)

o-An i si di ne C8CI

)

GB (exp) • 200.2+/-2 kcal/mol Temperature •' 6 00 K

PA (exp) ' 217.4+/-2 kcal/mol Temperature • 600 K

Yamdaqni , R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha , omeqa-Di ami nes,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used : MS

Entropy change assumed zero Equilibrium; scale based on CH3NH2
348 -

C7H9NO

~T

I CAS REGN -•

1 104-94-9

C

c’ 'c**N

C**0**C C

'c'

Sensenamine, 4-methoxy- (9CI)

p

- A n i s i d i n e (SCI)

GB (exp) : 203.9+/-2 kcal/mol

i

I Temperature

1

: 30 0 K

i

PA (exp) : 212.3+/-2 kcal/mol

~r

T emper a tu r

e

J _

: 3 0 0 K

Unpublished work by Uolf, Staley, Koppel,

f'clver, Beauchamp, and Taft.

T aaqepera

,

f

1

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
349

C7H9N0 j CAS REGN : 536-90-3

C

c" c

C#*0**C C**N

"c*

Bcnzenami ne, 3-methoxy- (9CI)

m-Anisidine (8CI)

PA (exp) • 214.0+/-2 kcal/mol T ernperature : 30 0 K

Summerhays, K. D., Pollack, S K., Taft, R. W . , and

Hehro, U . J

.

Gas-Phase Basicities of Substituted Anilines.

Inferences about the Role of Solvent in Dictating Site

of Protonation,

J. Am. Chain

.

Soc. 99, 4585 ( 1977 ).

Method used : ICR

Calculated entropy

Equilibrium; scale base on NH3. Ring protonation
350

C7H10 | CAS REGN : 498-66-8

C**xx*C

* * X 7C c*c+c*c

K X

x x c

B i cyclo [ 2 . 2 . 1 ] hopt-2-ene (9CI)

2-Horbornene (8CI)

PA ( exp) : 198. 8+/ -2 keal/mol Temperature : 300 K

Staley, R

.

H., Wietinq, R. D. and Beauchamp, J. L. Carbenium Ion Stabilities in -the Gas Phaso and

Solution. An Ion Cyclotron Resonance Study of

Bromide Transfer Reactions Involving Alkali Ions,

Alkyl Carbenium Ions, Acyl Cations, and Cyclic

Halon i urn Ions,

J. Am. Cham. Soc. 99, 5969 (1977).

Method used : ICR

Calculated entropy

Equilibrium relative to Et20; scale based on NH3
35 1

I C7H10N2 CAS REGN : 1 122-58-3

C*#N#*C

*

* . . c c

4~Py r i d i nam i ne > N , N~di methyl- (9CI)

Pyridine, 4~ ( d i methy lam i no ) - (8CI)

GB ( exp

)

224.90+/-2 kcal/mol T cmperature 30 0 K

PA ( exp

)

232.70+/-2 kcal/mol 7 emperature 30 0 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on Nrl3

GB (exp) : >209.7 kcal/mol Temperature : 423-473 K

Dzi di c , I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry

,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used • MS

Bracketing relative to (CH3)2NH
352

C7H 12

1 CAS REGN : 591-49-1

L

C

X X

X X C C

+ X

+ X C**C C

X. X

X X C

Cyclohexene, 1-methyl- (8CI9CI)

G3 (exp) : 188.‘t+/-2 kcal/mol Temperature : 300 K

PA (exp) • 196.6+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
353

C7H 12

I

| CAS REGN : 765-47-9

Cxxxxxc

x x

X X CXXC C

+ X

+ X C

XXC

Cyc 1 opent ene , 1,2-dimethyl- (8CI9CI)

GB (exp) 188.4+/-2 kcal/mol T emperature 298 K

Pollack, S. K., Wolf, J. F., Levi, B. A., Taft, R. U.,

and Hehre, W. J. Kinetic Detection of Common Intermediates in Gas

Phase Ion-Molecule Reactions,

J. Am. Chem. Soc. 99, 1350 (1977).

Method used : ICR
354

C7H13H

r CAS REGN : 100-76- 5

C**N

x xx

X C X C K C

X c *

X * X C**C

1-Azabi cyclo[2 . 2 . 23octane (9CI)

Quinuclidine ( 8 C I

)

GB (exp) : 220.8C+/-2 kcal/mol T emperature : 300 K

PA (exp) •* 228.60+/-2 kcal/mol T emperature : 300 K

Unpublished work by Wolf, Staley, Koppel

,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 220.80+/-2 kcal/mol T empera tu r

e

: 2 98 K

PA (exp) : 223.60+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydroqen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Potent i a 1 s

,

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2

Continued on next page
355

GB (exp) • 209.7 kcal/mol Temperature : 423-473 K

Dz i die, I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used : MS

Bracketing relative to ( CH3 ) 2MH

C7H 1 7 N CAS REGN : 1 1 1-68-2

C*«CX*C**C**C**CK*CX*N

1 -Heptanam i ne (9CI)

Heptylamine (8CI)

GB (exp) : 208.2+/-2 kcal/mol Temperature • 298 K

PA (exp) • 216.5+/-2 kcal/mol Temperature •' 293 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Evaluation of Intramolecular Strong

Hydrogen Bonding in the Gas Phase,

J. Am. Chem. Soc. 95, 2669 (1973).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
356

C7H17N

r

CAS REGN : A458-3 1 -5

Cxxcxxnxxcxxcxxc

X

XC

X

X

C

1 -Propanam i ne , N,N-diethyl- (9CI)

Propylamine, N,N -diethyl- (8CI)

GB (exp) : 221.3+/-2 kcal/mol T emperature : 298 K

i

PA (exp) : 229.1+/-2 kcal/mol T emperatu r

e

: 298 K

Aug, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydroqen Affinities of A 1 ky lam i nes

,

J. Am. Chetn. Soc. 98, 3 11 ( 1976 ).

i

i Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
357

C7H17N I CAS REGN : 10076-31-0

C

X

X C#*N*xc*xc**C

x x

x x C C

1-Propanami ne, M , N , 2 , 2-tetramethyl- (9CI)

Propylamine, N , N , 2 , 2-tetramothyl- C8CI)

I GB (exp) • 218.6+/-2 kcal/mol Temperature : 300 K

| PA (exp) " 226.<++/-2 kcal/mol Temperature •' 300 K

Unpublished work by klolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
358

C7H18N2 CAS REGN : 110-95-2

. C**Nx*C**C**C**N**C

^ *

c c

1 , 3-Propanedi ami ne, N , N , H

' , N ' -tetramethy 1- (8CI9CI)

GB (exp) : 227.7+/-2 keal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel , Taagepera,

Mclver, Beauchamp, and Taft.

Method used *• ICR

Equilibrium; scale based on NH3
359

C8H4D6 | CAS REGN : 25493-13-4

D

X

X D**C**C

XD C

C D

x

x C**C*XD

x

xD

Benzene, 1,4-(dimethyl-d3)~

GB ( exp

)

182.9+/-2 keal/mol T enperature 300 K

PA (exp) 189.8+/-2 keal/mol T emperature 300 K

A u s 1 o o s , P . , and Lias, S. G. Equilibrium Iso-bops Effects on the Proton Transfer

Reactions of Me thy 1 benzenes

,

J. Am. Chem. Soc. 99, 4198 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
360

C8H5F30 | CAS REGN : 455-19-6

C

F C C**C++0

** F**C**C C

*

X - . . F C

Benzaldehyde, 4- ( t r i fl uo r omet hy 1

) - C9CI)

p-To 1 ua 1 dchyde , . alpha alpha alpha . -tr i fluoro- (8CI)

GB (exp) : 181.3+/-2 kcal/mol Temperature • 300 K

PA (exp) : 189.1+/-2 kcal/mol Temperature : 300 K

Unpublished work by Ulclf, Staley, Koppel , Tasgepera,

Nclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C8H5N0 I CAS REGN : 105-07-7

I C

c c#*c++o

Nft#C**C C

’c’

Benzon i t r i 1 e , 4-formyl- (9CI)

Terephthalaldehydoni tr i 1 g (8CI )

GB (exp) : 177.6+/-2 kcal/mol Temperature ; 300 K

PA (exp) ; 185.4+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used •' ICR

Calculated entropy

Equilibrium; scale based on NH3
362

C8H8

n

CAS REGH : 100-42-5

c

c'

" c

C++CX*C c

c’

Benzene

,

ethenyl- ( 9CI

)

Styrene ( 8CI )

GB ( exp

)

: 191.5+/-2 kcal/mol Temperature : 300 K

PA ( exp

)

: 199.3+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5A17 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
363

C8H80

r

CAS REGN = 98-86-2

C

C* C

Cx*C**C C

+

+

0 C

Ethanone , 1-phenyl - ( 9 C I

)

Acetophenone (SCI)

GB (exp) : 195.3+/-2 k ca 1/mo

1

Temperature : 300 K

PA (exp) : 203. 1+/-2 kca 1/mo 1 Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagcpera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
364

1

j C8H80

1

1 CAS REGN : 104-87-0

1

C

c c**c

j o++c**c c V

1 Benzaldehyde, 4-methyl- (9CI)

1 p~To 1 ua 1 dehyde (8CI)

1 GB (exp) : 194+/-2 kcal/mol Temperature • 300 K

1 PA (exp) : 201.8+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel , Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
365

C8H802 I CAS REGN : 93-58-3

C

c’ C

C*xO**C*#C C

+

+ . . 0 c

Benzoic acid, methyl ester (8CI9CI)

GB ( exp

)

193. 1+/-2 keal/mol T emperature 300 K

PA C exp

)

200 . 9+/-2 keal/mol T emperature 30 0 K

Unpublished work by Wolf, Staley, Koppel, Taagepora,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
366

I C3H802

| CAS REGN : 123-11-5

C

c CX*0**C

| 0 + + C ¥ * C c V

i Benzaldshyde, 4-methoxy- (9CI)

j p- An i sa 1 dehyde (8CI)

G3 (exp) : 2C3.0+/-2 keal/mol Temperature : 300 K

PA (exp) ; 210.8+/-2 keal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclvor, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on UH3
C8H10 | CAS REGN •• 95-47-6

C. .C

c**c c

c. .c*

X

Xc

Benzene, 1,2-dimethyl- (9CI)

o~Xy 1 ene ( SCI

)

GB (exp) 183+/-3 kcal/mol T emperature 340 K

PA (exp) 190+/-3 kcal/mol T emperature 340 K

Chong, S. L., and Franklin, J. 1.,

Proton Affinities of Benzene, Toluene, and the Xylenes,

J. Am. Chem. Soc. 94, 6630 (1972).

Method used • MS

Equilibrium relative to CH35H and (CH3)20

Entropy change assumed zero Continued on next page
368

GB (exp) : 183.7+/-2 kcal/mol Temperature • 300 K

PA (exp) •' 191.1+/-2 kcal/mol Temperature * 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia From Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
369

C8H10 I CAS REGN : 10 0-4 1-4

I

C

c’ c

C*xC**C C V

Bensene, ethyl- (8CI9CI)

GB (exp) • 181.8+/-2 keal/mol T emperature 300 K

Hehre, W. J., M elver, R. T., Jr., Pople, J. A.,

and Schleyer, P. v. R.,

Alkyl Substituent Effects on the Stability of

Protonated Benzene,

J. Am. Chem. Soc. 96, 7162 (1974).

Method used : ICR

Equilibrium; scale based on C6 H5CH3 ( To 1 uene

)

Continued on next page
370

GB (exp) : 175.1+/-2 kcal/mol Temperature : 600 K

PA (exp) * 190.6+/-2 kcal/mol Temperature : 600 K

L a u , Y. K . , and K e b a r 1 e , P. Substituent Effects on the Intrinsic Basicity of

Benzene : Proton Affinities of Substituted Benzenes,

J. Am. Chem. Soc. 98, 7952 (1976).

Method used : MS

Calculated entropy

Equilbrium relative to C6H6. Usinq GB (C6H6) = 167.3+/-2 and PA (C6H6) = 181.2+/-2

GB (exp) 180 . 9+/-2 kcal/mol T emperature 30 0 K

PA (exp) 189 . 1+/-2 kcal/mol T emperature 30 0 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on C6H6 ( Benzene)

Continued on next page
GB (exp) : 181.8+/-2 kcal/mol Temperature : 300 K

PA (exp) : 189.6+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclvcr, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5917 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

i

i
372

C8H10 | CAS REGN : 106-42-3

C

C C**C

C**C C

c

Benzene, 1,4-dimethyl- C9CI)

p-Xylene ( 8CI

)

GB (exp) 182+/-3 k ca 1/mo 1 T einper atu r e 340 K

PA (exp) 1S9+/-3 k ca 1/mo 1 T emperature 340 K

Chonq, S. L., and Franklin, J. L.,

Proton Affinities of Benzene, Toluene, and the Xylenes,

J. Am. Chem. Soc. 94, 6630 (1972).

Method used •' MS

Equilibrium; scale based on CH3SH and (CH3)20

Entropy change assumed zero

GB (exp) : 182.9+/-2 kcal/mol

j

| Temperature

| 300 K

PA (exp) • 139.8+/-2 kcal/mol

1

| Temperature

1 300 K

Devlin, J. L., Ill, Wolf, J. F., Taft, R. W., and

Hehr e , W . J .

,

The Proton Affinities of Toluene,

J. Am. Chem. Soc. 98, 1990 (1976).

Method used • ICR

Calculated entropy

Equilibrium relative to C6 H6 ( Benzene

)
373

C8H10

n

CAS REGM : 1 08-38 -3

C

c’ c

c**c c**c

V

Benzene, 1,3-dimethyl- (9CI)

m-Xylene (SCI

)

GB (exp) '• 182 + /-3 kcal/mol T emperature : 340 K

PA (exp) : 189.7+/-3 kcal/mol T emperature : 340 K

Chong, S. L., and Franklin, J. L.,

Proton Affinities of Benzene, Toluene, and

J. Am. Chem. Soc. 94 , 6630 (1972).

the X y 1 e n e 5

,

Method used : MS

Equilibrium relative to CH3SH

Entropy change assumed zero and ( CH3 ) 20

G3 (exp) • 187.2+/-2 kcal/mol Temperature : 298 K

PA (exp) '• 194.6+/-2 kcal/mol T emperature : 298 K

Devlin, J. L., Ill, Wolf, J. F., Taft, R. W., and

Hehr e , W . J .

,

The Proton Affinities of Toluene,

J. Am. Chem. Soc. 98, 1990 (1976).

Method used : ICR

Calculated entropy

Equilibrium relative to C6H6 ( Benzene

)
374

C8H 1 IN CAS REGN : 103-69-5

C

c’ C

C**CX*N**C C

c

Benzenamine, N~ethyl~ (9CI)

Aniline, N-ethyl- (SCI)

G3 (exp) : 203 . 6+/~2 kcal/mol Temperature : 600 K

PA (exp) s 220 .S+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bondinq

in Proton-Bound Amine Dimers and Proton -Induced

Cyclization of alpha, omeqa-Dia mines,

J. Am. Cham. Soc. 95, 3504 (1973).

Method used • ICR

Equilibrium; scale based on NH3

Entropy change assumed zero
375

C8H11N I CAS REGN : 121-69-7

C

C* 'c

C*xN**C C

** . . C C

Benzenamine, N , N~d i methyl - (9CI)

Aniline, N , N~di methyl- (8CI)

GB (exp) : 212.3+/-2 kcal/mol T emperatur

e

300 K

PA (exp) ' 220.1+/-2 kcal/mol T emporature 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

PA (exp) 220+/-2 kcal/mol T emperature 298 K

Pollack, S. K., Devlin, J. L., Ill, Summerhays, K. D.,

Taft, R. W., and Hehre, W. J. The Site of Protonation in Aniline,

J. Am. Chem. Soc. 99, 4583 C1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3. Protonation on the

n i trogcn

Continued on next page
376

GB (exp) : 206.8+/-2 kcal/mol Temperature : 600 K

PA (exp) • 224+/-2 kcal/mol Temperature • 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydrogen Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha , omeqa-Di amines,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used • MS

Equilibrium; scale based on NH3

Entropy change assumed zero

GB (exp) >209.7 kcal/mol Temperature 423-473 K

Dzi di c , I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used : MS

Bracketing relative to (CH3)2NH
377

C8H 18S CAS REGH : 107-47-1

L_

C C

X X

X X c**c**s#*c**c

X X

X X c C

Propane, 2,2'-thi obi sC2-methyl- (9CI)

tert-Butyl sulfide (8CI)

GB (exp) • 203.0+/-2 kcal/mol Temperature • 300 K

PA (exp) : 210.4+/-2 kcal/mol Temperature •' 30 0 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
378

I C8H19N

1 CAS REGN : 1 10-96-31

| C**C**C**N**C**C**C

* x

x x C C

1 -P r opanam i ne , 2-methyl-N- ( 2-methyl propyl ) - (9CI)

| Di i sobutylami ne (8CI)

GB (exp) : 217.7+/-2 kcal/mol Temperature • 298 K

PA (exp) • 22S.9+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
379

C8H19N

r

CAS REGN : 1 1 1-92-2

Cxxc**C**C**N**C**C**C**C

1-Cutanamine, N-butyl- (9CI)

Dibutylamine (SCI)

GB (exp) • 217.20+/-2 kcal/mol Temperature : 298 K

PA (exp) 225.A0+/-2 kcal/mol T emperature : 298 K

Aue, D. H., Webb, H. M . » and Bowers, M. T. Quantitative Proton Affinities, Ionization

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Potent i al s,

Method used = ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
380

CSH 19N CAS REGN : 626-23-3

C*xC**C**N**C**C**C

x x

X X c c

2-Butanami ne , N-( 1-methylpropyl )-

Di -sec-butylami ne (8CI)

( 9CI

)

GB (exp) •’ 219.9+/-2 kcal/mol Temperature : 298 K

PA (exp) : 228.1+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Hebb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydroqen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
38 1

C8H 19H | CAS REGN : 7087-68-5

CXXC**N**C**C

x x x xxx

c c c

x

xc

2-Propanami ne, N-ethy 1 -N- (

1 -methyl ethyl ) - (9CI)

Tr i ethylam i ne , 1 , 1

' ~d i methyl - (8CI)

GB (exp) : 223.6+/~2 kcal/mol Temperature •' 30 0 K

PA (exp) s 231.4+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
382

CSH19N | CAS REGN : 21981-37-3

C C

* *

x * C**C**N**C**C

* x x x C C

2-P ropsnam i ne , N- ( 1 ,

1 -d i methyl ethyl ) -2-methyl - C9CI)

Di -tart-butylami ne (8CI)

GB (exp) s 221.7+/-2 kcal/mol Temperature • 300 K

PA (exp) : 229.9+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used ; ICR

Calculated entropy

Equilibrium; scale based on NH3
383

C8H20N2 CAS REGH = 111-51-3

C*XNK*C**C**C**C**N**C

* X

X X C C

1 , 4-Butanedi ami ne, N , N , N

' , N ' - tet ramethy 1 - (8CI9CI)

GB (exp) : 229.3+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Equilibrium; scale based on NH3
C9H9C1 | CAS REGN : 1712-70-5

C

C C**CL

C**C**C C

+ . + . . c c

Benzene, 1 -chi o ro-4- ( 1 -methyl e-fchenyl ) - (9CI)

Styrene, p-chloro- . alpha . -methyl- (8CI)

GB (exp) : 195.2+/-2 kcal/mol Temperature 300 K

PA (exp) : 203+/-2 kcal/mol Temperature * 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
385

C9H9F

r

CAS REGN : 350-40-3

C

C C**F

c**c**c C

+ . + . . C C

Benzene, 1 -fl uo ro~4 _ (

1 -methyl ethenyl ) - (9CI)

Styrene, p-fluoro- . alpha . -methyl- (8CI)

GB (exp) • 196.9+/-2 kcal/mol T emperature : 300 K

PA (exp) ’ 204.7+/-2 kcal/mol T emperature : 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

Taaqepera

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
386

C9H9N | CAS REGN : 6921-29-5

C#8C**C*XNX*CX*C#SC

X

xC

x

*c

#

#c

2-P rcpyn- 1 -am i ne , N , N-d i -2-propynyl - (9CI)

Tri -2-propynylami ne (8CI)

GB ( exp

)

209.3+/-2 k ca 1/mo 1 Temperature 300 K

PA C exp

)

217 . 1+/-2 kcal/mol T emperature 300 K

Unpublished work by l-Jolf, Staley/ Koppel/ Taagepera

,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
337

1 C9H10

1 CAS REGN : 98-83-9

C

c’

’ c

| C**c**c c

++ . . c c

Benzene, (

1 -methylethenyl ) - (9CI)

I Styrene, . a 1 pha . -methyl- (8CI) * •

GB (exp) : 197.0+/-2 kcal/mol Temperature : 300 K

PA (exp) : 205.2+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
388

C9H12 | CAS REGN : 98-82-8

C

C C

c**c#*c c

x . . x . . c c

Benzene, ( 1 -methyl ethyl ) - (9CI)

Cumene ( 8CI

)

GB (exp) 183+/-2 kcal/mol T emperature 300 K

Hehre, W. J., Mclver, R. T., Jr., Pople, J. A.,

and Schleyer, P. v. R.,

Alkyl Substituent Effects on the Stability of

Protonated Benzene,

J. Am. Chem. Soc. 96, 7162 (1974).

Method used • ICR

Equilibrium; scale based on C6 H5CH 3 ( To 1 uene

)

Continued on next page
389

GB (exp) • 182.2+/-2 kcal/mol Temperature : 300 K

PA (exp) : 190.4+/-2 kcal/mol Temperature : 300 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Mea surement s

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on C6 H6 ( B enzene

)
390

C9H 12 CAS REGN : 103-65-1

C

c'

" C

C**C**C**C C

' c"

Benzene, propyl- (8CI9CI)

GB (exp) • 182.6+/-2 kcal/mol T emperature 300 K

Hehre, W. J., Mclver, R. T., Jr., Pople, J. A.,

and Schleyer, P. v. R.,

Alkyl Subst i tuent Effects on the Stability of

Prctonated Benzene,

J. Am. Chem. Soc. 96, 7162 (1974).

Method used : ICR

Equilibrium; scale based on C6 H5CH3 ( To 1 uene

)

Continued on next page
391

GB (exp) : 181.8+/-2 kcal/mol Temperature • 300 K

PA (exp) • 190+/-2 kcal/mol Temperature : 300 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on C6H6 ( Benzene

)

GB (exp) •' 182.6 + /-2 kcal/mol Temperature : 300 K

PA (exp) • 190.4+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used ’ ICR

Calculated entropy

Equilibrium; scale based on NH3
392

1

1 C9H12

1

1 CAS REGN s 108-67-8

1

C

*

c

c' ’c

1 c**c c**c

c

I Benzene, 1 , 3, 5~tri methyl- (9CI)

I Mesitylene (8CI)

1 GB (exp) '• 191.3+/-2 kcal/mol Temperature : 300 K

I PA (exp) '• 198.4+/-2 kcal/mol Temperature '• 300 K

Devlin, J. 1., Ill, Wolf, J. F., Taft, R. U., and

Hehre , W . J . , The Proton Affinities of Toluene,

J. Am. Chem. Soc. 98, 1 990 ( 1 976 ).

Method used ' ICR

Calculated entropy

Equilibrium relative to benzene
393

C9H 1 2N206 CAS REGN : 58-96-8

C++C 0*#C XXX X XX XX

OXXCXxHxxxxxc X xx X x x x HXXC C**C

X xx X * 5 0 0

Uridine (8CI9CI)

PA (exp) : 207+/-5 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J . A. , Chemical Ionization Mass Spectrometry of Nucleosides,

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used • MS

Bracketing relative to NH3 and CH3NH2.
394

C9H 13N

C

I CAS REGN : 121-72-2

C CC**N**C CXXC

x

x . . C C

Bencenamine, N , N , 3~tri methyl- (9CI)

m-Toluidine, N , N~d i methyl - (8CI)

PA ( exp

)

221+/-2 kcal/mol Temperature 298 K

Pollack, S. K., Devlin, J. L., Ill, Summerhays, K. D. Taft, R. W., and Hehre, W. J. The Site of Protonation in Aniline,

J. Am. Chem. Soc. 99, 4583 (1977).

Method used ' ICR

Equilibrium; scale based on NH3. Protonation on the

n i trogen
395

C9H 13N

n

CAS REGN = 613-97--8

c

c’

’ c

C*XC**N#*C

X c

KC c

Benzenami ne Aniline, N-

, N-ethyl-N-methyl- (9CI)

ethyl-N-methyl- (8CI)

GB (exp) • 209.40+/-2 kcal/mol Temperature : 600 K

PA (exp) • 226.60+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydroqen Bonding

in Proton-Bound Amine Dimers and P roton- Induced

Cyclization of alpha , omeqa-D i am i nes

,

J. Am. Chem. Soc. 95, 3504 (1973).

Method used • MS

Entropy change assumed zero Equilibrium; scale based on NH3
396

C9H 13N305 | CAS REGN : 65-46-3

J

C + + C

x x X X n y.y.c XXn*****c

X % X X N%%C

%

%

0

Oxxc

x x

x xX

X

X Cxxc

X X

X 3 0

Cy t i di ne (9CI)

PA (exp) >222 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Af f i n i ty

,

J. Am. Chem. Soc. 97, 3436 C1975).

Method used • MS

Bracketing relative to ( C H 3 ) 3 N .
397

C9H14N206

C**C

x x

x x 0%%C Nxxxxxc

% x x % x x N%%C

% x % x

0 0

Oxxc

x x

X

X

X

X Cxxc

| CAS REGN : 5627-05-4

Uridine, 5,6-dihydro- (9CI)

Hydrouracil, 1 - . beta . -D-r i bof uranosyl- (8CI)

PA (exp) : 207+/-5 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J . A. , Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used ’• MS

Bracketing relative to NH3 and CH3NH2.
398

1

I C9H15N

1 CAS REGN : 102-70-5

! C++C**C**N**C**C++C

. *

1 c

*

Xc

+

+c

I 2-Propen- 1-ami ne, N , N~d i -2-propeny 1- (9CI) I

I Triallyl amine C8CI)

GB (exp) : 219+/-2 kcal/mol Temperature : 300 K

PA (exp) : 226.8+/~2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on HH3
399

C9H21N I CAS REGN : 102-69-2

CXXC**C**N**C**C**C

*

KC

x

XC

X

X

c

1-Propanami ne, N , N~di propyl- (9CI)

Tr i propylami ne (8CI)

G3 (exp) '• 223.1+/-2 keal/mol Temperature : 300 K

PA (exp) : 230.9+/-2 keal/mol Temperature ’• 300 K

Unpublished work by Wolf, Staley, Koppel, Taagcpera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) : 222.8+/-2 keal/mol Temperature • 298 K

PA (exp) • 230.60+/-2 keal/mol Temperature • 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

A Thermodynamic Analysis of Solvation Effects on the

Basicities of Alkylamines. An Electrostat i c Analysis

of Substituent Effects,

J. Am. Chem. Soc. 98, 318 (1976).

Method used : ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
400

C9H21N | CAS REGN : 2085-66-7

C C

X x

x x Cxxc**N**C**C**C

x x x x C C

Propylamine, N-tert-butyl- 1 , 1-di methyl- (8CI)

GB (exp) : 221.9+/-2 kcal/mol Temperature : 298 K

PA (exp) • 230.1+/-2 kcal/mol Temperature : 298 K

Aue, D. H., Webb, H. M., and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkylamines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used • ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
1

I C10H8

1 CAS REGN = 275-51-4

c c

c c c

. * X .

[ c c

1 c c

i

c*

I Azulene (8CI9CI)

j

I

GB (exp) '• 215.9+/-2 kcal/mol Temperature • 300 K

I PA (exp) : 223.3+/~2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclvor, Beauchamp, and Taft.

Method used = ICR

Calculated entropy

Equilibrium; scale based on NH3
1

I C10H9F3

1

1 CAS REGN : 55186-75-9

1

C

F C C**C**C

* +

* + F**C**C C C

** . . F C

I Benzene, 1 -( 1 -methyl ethenyl ) -4- ( t r i fl uoromethyl ) - (9CI)

I GB (exp) : 139.3+/-2 kcal/mol Temperature : 300 K

PA Cexp) : 197.1+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
403

CIOHIOFe I CAS REGN : 102-54-5

C+++C C+++C

x x x x

x x x x

xxxC**Fe**C xxx xx xx

C+++C C+++C

Ferrocene (8CI9CI)

PA (exp) : 208+/-4 kcal/mol T emperature 300 K

Foster, M. S., and Beauchamp, J. L.,

Ion-Molecule Reactions and Gas-Phase Basicity

of Ferrocene,

J. Am. Chem. Soc. 97, 4814 (1975).

Method used : ICR

Bracketing relative to CH3N-NCH3 and CH3NH2.
404

C 1 0H 1 2 | CAS REGN : 1 195-32-0

C

C C**C

C**C**C C

++ . . c c

Benzene, 1 -methyl-4- (

1 -methyl ethenyl ) - (9CI)

Styrene, p, . alpha . -di methyl- C8CI)

GB (exp) : 200.8+/-2 keal/mol Temperature : 300 K

PA (exp) • 208.6+/-2 keal/mol Temperature '• 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
405

C 1 OH 1 2N404 CAS REGN : 550-33-4

0

X

X N + + C C

X x X

X X X o o * o**c

X X X X X X

N Cxxh*xxxxc X

# 9 X X

m # X X C. .N c**c

X X

X X 0 0

9H -Purine, 9-. beta. -D-r i bofuranosyl- (8CI9CI)

PA Cexp) • >222 kcal/mol Temperature •

Wilson, M

.

S., and McCloskey, J . A . , Chemical Ionisation Mass Spectrometry of Nucleosides.

Meehan i sms of Ion Formation and Estimations of

Proton Affinity,

J . Am . Chem . Soc. 97, 3436 (1975).

Method used : MS

Bracketi ng relative to (CH3)3N.
406

C 1 OH 1 20 CAS REGN : 1712-69-2

c'

C**C**C

+ • . +

c

C

Cxxoxxc

C

c

Benzene

,

An i sole.

1 -methoxy-4- (

1 -methyl ethenyl ) - (9CI)

p- i sopropenyl- (8CI)

GB (exp) : 206.8+/-2 kcal/mol Temperature - 300 K

PA ( exp

)

• 214.6+/-2 kcal/mol Temperature '• 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ' ICR

Calculated entropy

Equilibrium; scale based on NH3
4 0 7

C10H13N

r

CAS REGN : L_

4096-21-3

C

C C C****#C

X X

* X C C****XN C

X *

. . X * C C

I Pyrrolidine, 1-phenyl- (8CI9CI)

I GB (exp) • 213.6+/-2 kcal/mol T emperature : 30 0 K

I PA (exp) : 221.4+/-2 kcal/mol T emperature •• 30 0 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
4 08

I C10H13N5 | CAS REGN : 715-91-3

c

N

* N

n*;%c c Cxxxxxc

. x X X

. . X X X C Nxxxxxc C

x x xx x x xx

N+++++C C

9H-Purin-1-amine, 9-cyclopentyl- (9CI)

Adenine, 9-cyclopentyl- C8CI)

PA (exp) • >222.1 keal/mol Temperature :

Wilson, M. S., and McCloskey, J . A. , ChGrnical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used •' MS

Bracketing relative to (CH3)3N
4 0 9

C10H13N504 | CAS REGN : 58-61-7

N%

%

C.

C. .N

N + + C

X X

E x

x

Ifx i CXXNXXXXXC

OXXC

X X

E X

X

E X

X * C**C

x x X X

0 0

Adenosine (8CI9CI)

PA (exp) • >222 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J . A . , Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Aff i ni ty,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used ’ MS

Bracketing relative to (CH3)3N.
C 1CH 14 | CAS REGN : 98-06-6

C

c c" c

*

C x x c * x C C

*

x . . c c

IcnsGne, ( 1 ,

1 -d i methyl ethyl ) - (9CI)

Benzene, tert-butyl- CSCI)

G3 (exp) : 133.2+/-2 kcal/mol Temperature : 300 K

Heli re, 14. J., Mclver, R. T., Jr., Pople, J. A.,

and Schicyer, P. v. R.,

Alkyl Substituent Effects on the Stability of

Proto listed Benzene,

J. Am. Chem. See. 96, 7162 (1974).

Method used : ICR

Equilibrium; scale based on C6H5CH3(Toluene)

Continued on next pag
411

GB (exp) ; 182.4+/-2 kcal/mol Temperature • 300 K

PA (exp) • 190.6+/-2 kcal/mol Temperature : 300 K

Yamdagni, R.» and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used • MS

Calculated entropy

Equilibrium; scale based on C6 H6 ( Benzene

)
4 12

C10H14 | CAS REGN : 104-51-8

C

c' C

C**C**C**C**C C

c

Benzene

,

butyl- (8CI9CI)

GB (exp) : 183+/-2 kcal/mol Temperature : 300 K

Hehre, l*J

.

J., Mclver, R. T., Jr., Pople, J. A.,

and Schleyer, P. v. R.,

Alkyl Substituent Effects on the Stability of

Protonated Benzene,

J. Am. Chem. Soc. 96, 7162 (1974).

Method used : ICR

Equilibrium; scale based on C6 H5CH3 ( Tol uene

)

Continued on next page
4 1 3

GB (exp) : 183+/-2 kcal/mol Temperature • 300 K

PA (exp) : 190.8+/-2 kcal/mol Temperature • 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. l\l . , Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3

G3 (exp) : 182.2+/-2 kcal/mol Temperature : 300 K

PA (exp) • 190.4+/-2 kcal/mol Temperature * 300 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ' MS

Calculated entropy

Equilibrium; scale based on C6H6 ( Benzene)
4 14

C10H14N2O5

1

| CAS REGN : 50-89-5

0

K*C**C

* x x x

X X X

X X

C

X

X 0**C**C * C++C

x x

x x 0**C*****N C%%0

^ %

x v C%%N

*

%

%

0

Thymidine (8CI9CI)

PA (exp) 207+/-5 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used : MS

Bracketing relative to NH3 and CH3NH2
9 1 5

C10H15N I CAS REGN : 91-66-7

C

c’ c

CXXCXXNXXC C

xX . . C C

X

XC

Benzenamine, N,N~diethyl~ (9CI)

Aniline, N,N-diethyl- (8CI)

GB (exp) : 212. 10+/-2 kcal/mol T emper atu r

e

600 K

PA (exp) • 229.30+/-2 kcal/mol T emperature 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities of Amines. Hydroqon Bonding

in Proton-Bound Amine Dimers and Proton-Induced

Cyclization of alpha , omeqa-Di ami nos,

J. Am. Chcm. Soc. 95, 3509 (1973).

Method used • MS

Equilibrium; scale based on NH3

Entropy change assumed zero
416

C10H19N | CAS REGN : 31023-92-4

C*XC

x X

X x C *N

X KCX jf X XC X C*C C

X X

X X Cxxc

1 -Azab i cyclo [ 3 . 3 . 3 ] undecane (9CI)

PA (exp) : 227.9+/-2 kcal/mol Temperature : 298 K

Aua, D. H., Webb, H. M., and Bowers, M. T.,

Photoelectron Spectrum and Gas-Phase Basicity of

Manxine. Evidence for a Planar Bridgehead Nitrogen,

J. Am. Chem. Soc. 97, 4136 C1975).

Method used : ICR

Equilibrium; scale based on CH3NH2

Van't Hoff plot
4 17

C10H23N | CAS REGH : 2016-57-1

NX*C**C**C**C**C**CX*C*XC**C**C

1-Decanamine (9CI)

Decylamine (8CI)

GB (exp) : >209.7 kcal/mol Temperature • 423-473 K

J

1

1 . D z i d i c , I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used : MS

Bracketing relative to (CH3)2NH
A 18

C10H24N2 | CAS REGN : 111-18-2

CX*N**C**CX*C**CX*C**C**N**C

X X

x x C C

1 , 6-Hexaned i ami ne , N , N , N

’ , N ' -tetramethyl- (8CI9CI)

GB (exp) 226.9+/-2 kcal/mol Temperature • 300 K

Unpublished work by Wolf, Staley, Koppel , Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Equilibrium; scale based on NH3
4 19

| C11H13N

1 1

| CAS REGN : 4363-25-1

1 1 N**C

XX X x c # C. .C x C

| . C * •

1 , XX

1 c c**c

c. .c*

2H- 1 , 4- Ethanoqu i no 1 i ne , 3,4-dihydro- (8CI9CI)

GB (exp) : 220.5+/-2 kcal/mol Temperature : 300 K

| PA (exp) • 228.3+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used • ICR

Calculated entropy !

t Equilibrium; scale based on NH3
420

C11H15N | CAS REGN : 4096-20-2

C C XX . . xx . Cxx.. C C C XX.. C Nxxxxxc C xx . . xx . . C C

Piperidine, 1-phenyl- (8CI9CI)

GB ( exp) 216.1+/-2 kcal/mol

\

| Temperature

1 300 K

PA ( exp

)

223. 9+/-2 k ca 1 /mol

~r

I Temperature

1 30 0 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used ICR

Calculated entropy

Equilibrium; scale based on NH3
42 1

I

I

I

C12H1 IN | CAS REGN : 122-39-4

C C

c’ *C C* C

C C#****N**C C

’ c’ V

Benzenamine, N-phenyl- (9CI)

D i phenylami ne (SCI)

GB (exp) • >193.7 kcal/mol T emperature 423-473 K

Dz i d i c , I . , Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used • MS

Bracketing relative to NH3
<+22

C 12H 16N206 I CAS REGN = 362-43-6

0

y.

c c

X X XX

C**0

xxx X X

x C*#C

x xx xx x 0**C x

x x

x x C*xo

x

xC

XX

0

4

C%%N

x %

N*

XX X XX X

x C + + C

x

Uridine, 2

? , 3 ' -0- (

1 -methy 1 ethy 1 i dene ) - (9CI)

Uridine, 2 ’

, 3 ’ -Q- i sopropy 1 i dene- C8CI)

PA (exp) : 207+/-5 kcal/mol Temperature :

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spect r omet ry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Affinity,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used : MS

Bracketing relative to CH3NH2 and NH3.
423

C12H 18 CAS REGN : 37-85-4

C C

* X

* x C. .C

c**c c**c

c. .c’

x x x x C C

Benzene, hexatnethyl- (8CI9CI)

GB (exp) : 197.7+/-2 kcal/mol Temperature : 300 K

PA (exp) • 205.0+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taaqepera,

Mclver, Beauchamp, and Taft.

Method used = ICR

Calculated entropy

Equilibrium; scale based on NH3
424

C12H19N j CAS REGN : 22025-87-2

C C. .C

x . , x Cxxn**C C

c. .c’

x

X Cxxc**C

xxC

Benzdnamine, 2- ( 1 , 1 -d i methyl ethyl ) -N , N-d i methyl - (9CI)

Aniline, o-tert-butyl ~N , N-d i methyl- (8CI)

GB Cexp) : 218+/-2 kcal/mol Temperature • 300 K

PA (exp) : 225.8+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
425

C12H27N I CAS REGN : 102-32-9

i C**C**C**C**N**C**C**C**C

*

Xc

*c

*

c

X

Xc

1-Butanami ne, N , N-d i butyl - (9CI)

Tr i butylami ne (SCI)

G3 (exp) • 224.1+/-2 kcal/mol Temperature ; 298 K

PA (exp) : 232+/-2 kcal/mol Temperature • 298 K

A u e , D. H . , Webb, H. M . , and Bowers, M. T.,

Quantitative Proton Affinities, Ionization Potentials,

and Hydrogen Affinities of Alkyla mines,

J. Am. Chem. Soc. 98, 311 (1976).

Method used ICR

Calculated entropy

Equilibrium; scale based on CH3NH2
426

i

I C13H10O

1

1 CAS REGN : 1 19-6 1-9

!

C C

•o•o

•o

•o

i c c**x**C**C C

j +

• •

"**

. • C 0 c

I Methanone, diphenyl- (9CI)

I Benzophenone (8CI)

GB (exp) : ~200.7+/-2 kcal/mol Temperature : 300 K

PA (exp) : "20S.1+/-2 kcal/tnol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
427

C13H130P j CAS REGN : 2129-39-7

C C

c' C 0 c' C

++

c C*#*x*P**C c

X

. . * . . c c c

Phosphine oxide, methyldi phenyl- (8CI9CI)

PA (exp) • 220+/-3 kcal/mol Temperature = ~400 K

Goff, S. D., Jelus, B. L., and Schwei zer, E. E. Electron Impact and Chemical Ionization Mass Spectra

of Alkyldiphenylphosphine Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used : MS

Bracketing relative to pyridine and Me3N scale based

on NH3
428

C13H17N505 | CAS REGN : 362-76-5

C

X

*C ***

x x x

0 C 0

x *

X X Zxxxxxc C+++++N

x x x x X X X X qxxc**C C*****N C xx x . . xx x . 0 C C%%0

N N

C%

%

N

Guanosine, 2 ' , 3

* -0- ( 1 -methylethyl i dene ) - (9CI)

Guanosine, 2 ' , 3 ' -0- i sopr opy 1 i dene- (SCI)

PA (exp) >222 kcal/mol Temperature •

Wilson, M. S., and McCloskey, J. A.,

Chemical Ionization Mass Spectrometry of Nucleosides.

Mechanisms of Ion Formation and Estimations of

Proton Af f i n i ty

,

J. Am. Chem. Soc. 97, 3436 (1975).

Method used ' MS

Bracketing relative to (CH3)3N.
42 9

C13H21N CAS REGN : L

585-48-8

C

c c’ *C C

x . . X

X X CXXC*XC C**C**C

x . . X x . . X C N C

Pyridine, 2 , 6 -b i s( 1, 1-dimethylethyl)-

Pyridine, 2 , 6 — d

i -tert~butyl- C8CI)

( 9CI

)

GB (exp) *• 220.6+/-2 kcal/mol T emperature : 300 K

PA (exp) : 228.4+/-2 kcal/mol T emperature •• 30 0 K

Unpublished work by Wolf, Staley, Koppel,

Mclver, Beauchamp, and Taft.

T aagepera

,

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
43 0

C14H 12 CAS REGN : 530-48-3

C C

•o•o c’ *c

C C**x**C**C C

+

. . + . . C c c

•

Benzene,

Ethylene,

1 , 1

' -ethenyl i deneb i s- (9CI)

1,1-diphenyl- (8CI)

GB (exp) : 201.4+/-2 kcal/mol Temperature : 300 K

PA ( exp

)

: 209.2+/-2 kcal/mol Temperature : 300 K

Unpublished work by Wolf, Staley, Koppel, Taagepera,

Mclver, Beauchamp, and Taft.

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3
C1AH150P | CAS REGN : 1733-57-9

C C

c’ C 0 C* C

+ . + C c##*x*P*xc C

. . x

. . x . . C C C

X

XC

Phosphine oxide, ethy 1 d i phenyl - (8CI9CI)

PA (exp) : 220+/-3 kcal/mol Temperature ~ A 0 0 K

Goff, S. D., Jelus, B. L., and Schweizer, E. E. Electron Impact and Chemical Ionization Mass Spectra

of Alkyldiphenylphosphine Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used ’ MS

Bracketing relative to pyridine and Me3N; scale based

on NH3
4 32

C15H170P | CAS REGN : 2959-75-3

C C

c' C 0 C* C

. . +

. . + C c***xxp*xc C

• • ^ •

. . * . . C C**C c

X

c

Phosphine oxide, C

1 -methy 1 ethyl ) d i phenyl - (9CI)

Phosphine oxide, i sopropyldi phenyl- (8CI)

PA (exp) : 220+/-3 kcal/mol Temperature : "400 K

Goff, S. D., Jelus, B. L., and Schweizer, E. E. Electron Impact and Chemical Ionization Mass Spectra

of A 1 ky Id i pheny 1 pho sph i ne Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used ' MS

Bracketing relative to pyridine and Me3N; scale

based on NH3
<+33

C15H170P CAS REGN : 4252-83-<+

0

+

+ C*#xpxx*C

*

x c c c c c

*

. . X . . c c c

X

Xc

Phosphine oxide, d i phenyl propyl

i

i

PA (exp) : 220+/-3 kcal/mol Temperature : "400 K

Goff, S. D., Jelus, B. L., and Schwei zcr, E. E. Electron Impact and Chemical Ionization Mass Spectra

of Alkyldi phenylphosphi ne Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used ' MS

Bracketing relative to pyridine and Me3N; scale based

on NH3
C16H190P | CAS REGN : Hot available

0+

+ Cxxpxxc

x

x C C C

x

XC XX

X X C C

Phosphine oxide, i sobutyldi phenylPA (exp) : 220+/-3 kcal/mol Temperature : ~A00 K

Goff, S. D., Jelus, B. L., and Schwei zer, E. E. Electron Impact and Chemical Ionization Mass Spectra

of Alkyldi phenyl pho sph i ne Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used : MS

Bracketing relative to pyridine and Me3N; scale based

on NH3
435

C16H190P | CAS REGN = 4233-13-0

C 0 C

. . + . . + c C***P#*KC c

X

* c c c c c

X

. . x . . c c c

X

xCXXC

Phosphine oxide, butyldi phenylPA (exp) • 220+/-3 kcal/mol Temperature “400 K

Goff, S. D., Jelus, B. L., and Schweizer, E. E. Electron Impact and Chemical Ionization Mass Spectra

of A 1 kyl d i phenyl pho sph i ne Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used : MS

Bracketing relative to pyridine and Me3N; scale

based on NH3
4 36

C17H210P | CAS REGN : Not available

C 0 C

. . + . .

. . +

c C**P**C c

*X c c c c c

X

. . X . . c c**c**c c

X

xC

Phosphine oxide, neopentyldi phenylPA (exp) : 220+/-3 kcal/mol Temperature ”4 0 0 K

Goff, S. D., Jelus, B. L., and Schwei zer, E. E. Electron Impact and Chemical Ionization Mass Spectra

of Alkyldi phenylphosphi ne Oxides,

Org. Mass Spectrom. 12, 33 (1977).

Method used : MS

Bracketing relative to pyridine and Me3N scale based

on NH3
437

C18H15N i CAS REGN : 603-34-9

C C

c’ C C C

C C*****NXXC C

X

. . X . . C X c

XX

c

c* c

c c

c

Benzenamine, N , N — cJ i phenyl- (9CI)

Tr i phenylami ne (8CI)

G3 (exp) : >202.9 kcal/mol T einperature 423-473 K

Dz i d i c , I .

,

Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Reactants in Chemical Ionization

Mass Spectrometry

,

J. Am. Chem. Soc. 94, 8333 (1972).

Method used •' MS

Bracketing relative to CH3NH2
4 38

C22H310P

r

CAS REGN : Not avai lable

C 0 C

, . + . . + C Cxxpxxc C

*

. x C c c c c

x

x . . c C C

X

Xcxxcxxcxxcxxcxxcxxcxxc

Phosphine oxide, decanyldi phenylPA ( exp

)

: 220+/-3 kcal/mol Temperature : ~<+00 K

Goff, S. D., Jelus, B. L., and Schwei zer, E. E. Electron Impact and Chemical Ionization Hass

of Alkyldi phenylphosphi ne Oxides,

Orq. Mass Spoctrom. 12, 33 (1977).

Spectra

Method used : MS

Bracketing relative to pyridine and Me3N scale based

on HH3
439

Ca CAS REGN : 7440-70-2

CA

Calcium (8CI9CI

)

PA (exp) : >211 kcal/mol Temperature : ~800 K

E s 1 a v a , L. A., and Porter, R. F.

A Kinetic Study of Proton Transfer Reactions of NH4+,

CH3NH3+, and PH4 + with Calcium Atoms,

Chem. Phys. Letters 52 368 (1977).

Method used : MS

Bracketing relative to N H 3 , PH3 and M e N H 2
440

C1H CAS REGN : 7647-01-0

CL 1

Hydrochloric acid (8CI9CI)

PA (exp) : 140+/-3 kcal/mol Temperature :

Haney, M. A., and Franklin, J L. , Mass Spectrometri c Determ i nat i on of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969)

Method used • MS

Absolute PA value estimated by assuming that

for reaction RH+ + RH -> R + RH2 + the delta

H ~5X TC.

TC z measured translat i onal energy of the products.

PA (exp) • >120 kcal/mol Temperature : 297 K

Fehsenfeld, F. C., and Ferguson, E. E. Rate Constants for the Reactions C1+ + H2 -> HC+ + and C1H+ + H2 -> C1H2+ + H,

J. Chem. Phys. 60, 5132 (1974).

Method used FAG

Found reaction C1H+ + H2 -> C1H2+ + H react rapidly.

Since reaction C1+ + H2 -> HC1+ + H + .22eV has a low exothermi ci ty, they assumed HC1+ to be in ground

vibrational state.
4 <+ 1

C sHO I CAS REGN : 2 135 1-79-1

CS*0

Cesium hydroxide (8CI9CI)

PA (exp) • 270.1 kcal/mol T emperature 300 K

Searles, S. K., Dzidic, I., and Kebarle, P.,

Proton Affinities of the Alkali Hydroxides,

J. Am. Chem. Soc. 91, 2810 (1969).

Method used : MS

PA derived from delta H of reaction M+ + H20 -> ( M 0 H 2 ) + .

1

I D2

1 CAS REGN : 7782-39-0

I H**H

I Deuterium (8CI9CI)

PA (exp) • 98+/-A kcal/mol Temperature :

Harris, H. H., Crowley, M. G., Grossheim, T. R.,

Woessner, P. J., and Leventhal, J. J.,

Binding Energy of H3+,

J. Chem. Phys. 59, 6181 (1973).

Method used : MS

Threshold measurement of CID of D3+ + HE~>D2 + D+ + HE. Correction for collision energies distribution.

Continued on next page
442

1

1

I PA (exp) : 103.8+/-1.1 kcal/mol Temperature :

1

1

I

Cotter, R. J., Rozett, R. W., and Koski, W. S.,

Reactions of H20+ and D20+ with Molecular Hydrogen.

I. Proton Affinity of Hydroqen,

J. Chem. Phys. 57, 4100 (1972).

i

1

1

Method used : MS

Threshold measurement of D20+

Correction for Doppler effect

+ D2 -> D3+ + OD.

D20 CAS REGN : 7739-20-0

1 o 1

I Water-d2 (9CI)

I Water, heavy (D20) (8CI)

PA (exp) : 167+/-3 kcal/mol Temperature '•

Cotter, R. J., and Koski, W. S.,

Reaction of D30+ with D2 : Proton Affinity of Water,

J. Chem. Phys. 59, 784 (1973).

Method used : MS

Correction for Doppler effects. Deuterium affinity.

Threshold measurement of D20+ + D20 -> D30+ + DO.
FH | CAS REGN : 7664^39-3

F

Hydrofluoric acid (8CI9CI)

PA (exp) : 112+/-2 kcal/mol T emperatur

e

300 K

Foster, M. S., and Beauchamp, J. L.,

Proton Affinity and Gas-Phase Ion Chemistry of

Hydrogen Fluoroide,

Inorg. Chem. 14, 1229 (1975).

Method used •* ICR

Calculated entropy.

Equilibrium relative to N2.

PA (exp) 94.3+/-1.4 kcal/mol Temperature 0 K

Nq, C. Y., Trevor, D. J., Tiedemann, P. W., Ceyer, S. T.,

Kronebusch, P. !_., Mahan, B. H., and Lee, Y. T. Photo i on i zat i on of Dimeric Polyatomic Molecules 1 Proton Affinities of H20 and HF,

J. Chem. Phys. 67, 4235 (1977).

Method used : PI

AP of H2F+ from (HF)2. No temperature correction

was applied in this surpersonic expansion
FO CAS REGN : 12061-70-0

F+0

Oxygen f luor i de

PA (exp) • 134+/-2 kcal/mol Temperature : 0 K

Berkowitz, J., Appelman, E. H., and Chupka, W. A. Photoionization of HOF with Ma55 Analysis,

J. Chem. Phys. 58, 1950 (1973).

Method used • MS

Threshold measurement of reaction HOF -> H0F+
445

F3N

r

CAS REGN s 7783-54-2

FX#N**F

X

XF

Nitrogen fluoride (NF3) (8CI9CI)

PA (exp) '• 151+/-10 kcal/mol Temperature : 300 K

Holtz, D., Beauchamp, J. L., Henderson,

Taft. R. W.,

Basicity of Nitrogen Trifluoride in the

Ion Cyclotron Resonance,

Inorg. Chem. 10, 201 (1971).

W . G . , and

Gas Phase by

Method used : ICR

Bracketing relative to C2H4 AND HCL.

i

I
F6S CAS REGN = 2551-62-4

F F

X X xx Fxxsxxf

X

* X

F F

Sulfur fluoride (SF6), (OC-6-11)- (9CI)

Sulfur fluoride (SF6) (8CI)

PA (exp) : <144 kcal/mol T emperature 298 K

Gorden, R., Jr., and Sieck, L. W.,

Ion-Nolecule Reactions in Isopropanol 5 Implications

for its Radiolysis,

J. Res. N3S 76A, 655 ( 1972) .

Method used : MS

Proton transfer from C2H6+ to SF6 not observed.
HI

I

1 CAS REGN : 10034-85-2

1

I

Hydriodic acid (8CI9CI)

PA (exp) : 145+/-3 kcal/mol Temperature •

Haney, M. A., and Franklin, J L. , Mass Spectrometri c Determ i na-fc i on of -the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used : MS

Absolute PA value estimated by assuming that

for reaction RH+ + RH -> R + RH2+; the delta H ~5X TC. TC = measured translational energy of the products.
448

HKO CAS REGN : 1310-58-3

K**0

Potassium hydroxide (8CI9CI)

PA (exp) • 263.5 kcal/mol Temperature : 300 K

Searles, S. K., Dzidic, I., and Kebarle, P.,

Proton Affinities of the Alkali Hydroxides,

J. Am. Chem. Soc. 91, 2810 (1969).

Method used : MS

PA value derived from delta H M+ + H20 -> (M0H2 ) +

.

of reaction:

HLiO CAS REGN : 1310-65-2

L I *0

Lithium hydroxide (8CI9CI)

PA (exp) : 241.6 kcal/mol Temperature : 300 K

Searles, S. K., Dzidic, I., and Kebarle, P.,

Proton Affinities of the Alkali Hydroxides,

J. Am. Chem. Soc. 91, 2810 (1969).

Method used : MS

PA value derived from delta H M+ + H20 -> (M0H2 )of reaction
HNaO

• :

• CAS REGN : 1310-73-2

NA*0

Sodium hydroxide (8CI9CI)

PA (exp) • 248.5 kcal/mol Temperature : 300 K

Searles, S. K., Dzidic, I., and Kobarle, P.,

Proton Affinities of the Alkali Hydroxides,

J. Am. Chem. Soc. 91, 2810 (1969).

Method used : MS

PA value derived from delta H of react i on M+ + H20 = ( M0H2 )

H2 CAS REGN = 1333-74-0

H**H

Hydrogen (8CI9CI)

PA (exp) : 99.9+/-1 kcal/mol Temperature :

Duben, A. J., and Lowe, J. P. Correlation Studies on H3+. I The Wavefunct i ons.

J. Chem. Phys. 55, 4270 (1971).

Method used : TC

SCF-MO-CI calculation.

Continued on next page
450

PA (exp) : 97 kcal/mol T emperature 298 K

Schwartz, M. E., and Schaad, J. J.,

Ab Initio Studies of Small Molecules Using Is Gaussian Basis Function. II. H3+,

J. Chem. Physics 47, 5325 (1967).

Method used : TC

SCF-MO-CI calculation.

1 1

1

1 1 PA (exp) : 101.5 kcal/mol

r i

| Temperature :

1

1 Burt, J. A., Dunn, J. L., McEwan, M. J., Sutton, M. M.,

Rocke, A. E., and Schiff, H. I.,

Some Ion-Molecule Reactions of H3+ and the Proton

Affinity of H2,

J. Chem. Phys. 52, 6062 (1970).

Method used : FAG

Bracketing relative to 02 AND N2.

PA (exp) 1 0 1+/-2 kcal/mol Temperature :

Cotter, R. J., Rozett, R. W., and Koski, W. S.,

Reactions of H20+ and D20+ with Molecular Hydrogen,

I. Proton Affinity of Hydrogen,

J. Chem. Phys. 57, 4100 (1972).

Method used : MS

Correction for Doppler effect.

Threshold measurement of H20 + + H2 -> H3+ + OH.

Continued on next page
PA (exp) : 96+/-A kcal/mol Temperature :

Harris, H. H., Crowley, M. G. Grosshei m, T . R .

,

Woessnor, P. J., and Leventhal, J. J.,

Binding Energy of H3 + , J. Chem. Phys. 59, 6181 (1973).

Method used : MS

Threshold measurement of CID of H3+ + He ->

H2 + H+ +He. Correction for collision energies

d i st r i but i on

.

H20 | CAS REGN : 7732-18-5

0

Water (8CI9CI)

PA (exp) 167+/-7 kcal/mol T emperature 323-373 K

Long, J., and Munson, B.,

Proton Affinities of Some Oxygenated Compounds,

J. Am. Chem. Soc. 95, 2427 (1973).

Method used ’ MS

Bracketing relative to CH20 and C2H4

Continued on next page
- 452 -

I PA (exp) : 182 kcal/mol Temperature :

Sherman , J .

,

Crystal Energies of Ionic Compounds and Thermochemical

Appl i cat i ons,

Chem. Rev. 11, 93 (1932).

Method used : CLE

Using thermochemi cal cycle the value of PACH20) was calculated from PA(NH3).

PA (exp) : 171+/-2 kcal/mol T emperature 296,355,426 K

Hopkins, J. M . , and Bone, L. I.,

Relative Proton Affinities of Hydrogen Sulfide and Water,

J. Chem. Phys. 58, 1473 (1973).

Method used : MS

Van’t Hoff plot

Equilibrium relative to H2S. Assume steady

state kinetics.

PA (exp) 165.8+/-1.8 kcal/mol Temperature : 0 K

Ng, C. Y., Trevor, D. J., Tiedemann, P. W., Ceyer, S. T.,

Kronebusch, P. L., Mahan, B. H., and Lee, Y. T. Photo i on i zat i on of Dimeric Polyatomic Molecules : Proton Affinities of H20 and HF,

J. Chem. Phys. 67, 4235 (1977).

Method used : PI

AP of H30+ from (H20)2. No temperature correction

was applied in this supersonic expansion

Continued on next page
453

I GB (exp) • 153.3+/-2 kcal/mol Temperature : 600 K

PA (exp) s 169.3+/-2 kcal/mol Temperature ; 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 162.3 + /-2 kcal/mol Temperature : 300 K

PA (exp) : 170.3+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel , I., Taaqepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L.» and Taft, R. W.>

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used • ICR

Calculated entropy

Equilibrium; scale based on NH3
j H2S CAS REGN : 7783-06-4

1

1 5

1 Hydrogen sulfide ( H2S ) (8CI9CI)

GB (exp) : 165.7+/-2 kcal/mol Temperature : 300 K

PA (exp) *• 173.9+/-2 kcal/mol Temperature : 300 K

Freeman, C. G., Harland, P. W , and McEwan , M . J

.

The Equilibrium H3S + + HCN = H2CN+ +H2S and the

Relative Proton Affinities of HCN and H 2 S , Intern. J. Mass Spectrom. Ion Phys. 27, 77 (1978).

Method used : FAG

Equilibrium relative to HCN; scale based on NH3

PA (exp) 173.3+/-2 kcal/mol Temperature : 296,355,426 K

Hopkins, J. M . , and Bone, L. I.,

Relative Proton Affinities of Hydrogen Sulfide and Water,

J. Chem. Phys. 58, 1473 (1973).

Method used ' MS

Equilibrium relative to H20

Van't Hoff plot

Continued on next page
455

1

1

1 PA (exp) ' 177.1+/-2 kcal/mol Temperature : 299,329,360 K

Wei, L. Y., and Bone, L. I.,

Ion-Molecule Reactions in Me'thanol and Hydrogen Sulfide,

J. Phys. Chem. 78, 2527 (1974).

! Method used : MS

Equilibrium; scale based on CH30H

Van’t Hoff plot

PA (exp) : 171 kcal/mol Temperature :

Haney, M. A., and Franklin, J. L.,

Heats of Formation of H30+, H3S+, and NH4+ by

Electron Impact,

J. Chem. Phys. 50, 2028 (1969).

Method used : El

Appearance potential by electron impact.

Correction for excess enerqy.

1

GB (exp) : 165.9+/-2 kcal/mol Temperature : 300 K

PA (exp) •" 173.9+/-2 kcal/mol Temperature : 300 K

Wolf, J. F. , Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

Continued on next page
456

GB (exp) : 156.4+/-2 kcal/mol Temperature : 600 K

PA (exp) : 172.4+/-2 kcal/mol Temperature : 600 K

Yamdagni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements

,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used : MS

Calculated entropy

Equilibrium; scale based on NH3

GB (exp) • 172.4+/-2.5 kcal/mol Temperature : 300 K

PA (exp) • 175.3+/-2.5 kcal/mol Temperature : 300 K

Meot-Ner (Mautner), M.» and Field, F. H. Proton Affinities and Cluster Ion Stabilities in

C02 and CS2. Application in Martian Ionspheric

Chem i st ry

,

J. Chem. Phys. 66, 4527 (1977).

Method used : MS

Calculated entropy

The measurements done in the temperature range of

400~650k. Using the Hoff plot the H and S at 300 k were derived. Equilibrium; scale based on NH3
457

H2Se | CAS REGN : 7783-07-5

SE

Hydrogen selenide (H2Se) (8CI9CI)

GB (exp) : 166 .7+/-2 kcal/mol T emperature : 30 0 K

PA (exp) ' 174.7+/-2 kcal/mol Temperature : 30 0 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L., and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used '• ICR

Calculated entropy

Equilibrium; scale based on NH3
H3N CAS REGH : 7664-41-7

N

Ammonia (8CI9CI)

PA (exp) ; >197 kcal/mol Temperature •

Chupka, W. A., and Russell, M E. , Ion-Molecule Reactions of NH3+ by Photo i on i zat i on

,

J. Chem. Phys. 43, 1527 (1963).

Method used : PI

NH3+ formed by photo i on i zat i on and react with H20.

PA (exp) : 206.4 kcal/mol Temperature :

Bleick, W. E.,

The Lattice Energies of the Ammonium Halides and

the Proton Affinity of Ammonia,

J. Chem. Phys. PA = 2, 160 (1934).

Method used : CLE

Using thermochemical cycle the PA is derived

from crystal lattice energy.

Continued on next page
45 9

I PA (exp) : 208 kcal/mol Temperature :

Haney, M. A., and Franklin, J. L.,

Heats of Formation of H30+, H3S+, and NH4+ by

Electron Impact,

J. Chem. Phys. 50, 2028 (1969).

Method used : El

Appearance potential by electron impact.

Correction for excess energy.

1 PA (exp) •' 194+/-7 kcal/mol Temperature :

Vetchinkin, 5. I., Pshenichnov, E. A., and Sokolov, N. D.,

The Effect of the Hydrogen Bond on the Energy of the

Ionic Lattice of Ammonium Chloride and Estimation

of the Proton Affinity of an Ammonia Molecule,

Zh. Fiz. Khim. 33, 1269 (1959).

Method used : CLE

PA from crystal lattice energy, correction for hydrogen bond.

I PA (exp) •’ 206+/-8 kcal/mol Temperature :

Sherman , J .

,

Crystal Energies of Ionic Compounds and Thermochemical

Applications,

Chem. Rev. 11, 93 (1932).

Method used : CLE

Using thermochemical cycle the PA values 209, 208.6

and 202.7 are derived from crystal lattice energy of

NH4C1, NHABr and NH4I respect i vely

.

Continued on next page
460

GB (exp) : 185.1+/-2 kcal/mol Temperature : 600 K

PA (exp) : 202.3+/-2 kcal/mol Temperature : 600 K

Yamdaqni, R., and Kebarle, P.,

Gas-Phase Basicities and Proton Affinities of Compounds

between Water and Ammonia and Substituted Benzenes from

a Continuous Ladder of Proton Transfer Equilibria

Measurements,

J. Am. Chem. Soc. 98, 1320 (1976).

Method used ' ICR

Calculated entropy

Equilibrium; scale based on PA(iso~C4H8)

GB (exp) : 193.7+/-2 kcal/mol Temperature : 300 K

PA (exp) : 202.3+/-2 kcal/mol Temperature ‘ 300 K

Staley, R. H., Taaqepera, M., Henderson, W. G.,

Koppel, I., Beauchamp, J. L., and Taft, R. W

,

Effects of Alkyl and Fluoroalkyl Substitution on the Heterclytic and Homolytic Bond Dissociation

Energies of Protonated Amines,

J. Am. Chem. Soc. 99, 326 (1977).

Method used *• ICR

Calculated entropy

Equ i 1 i br i urn

.

Continued on next page
PA (exp) 205.7+/-1 kcal/mol T emperature 298. 15 K

Meot~Ner (Mautncr) , M., and Field, F. H. Proton Affinities and Cluster Ion Stabilities in

CG2 and CS2. Application in Martian Ionspheric

Chem i st ry

,

J. Chem. Phys. 66, 4527 (1977).

Method used ’ CLE

Using thermochemical cycle the PA value is derived

from crystal lattice energy. Error due to some of

the thermochemical data and the similarity of

I crystal structure.

| PA (exp) : 205.3 kcal/mol Temperature •

Goodliffe, A. L., Jenkins, H. and Haddington, T. C.,

D. B., Martin, S. V.,

The Proton Affinity of Gaseous Ammonia, the Charge

Distribution on the NH4+ Ion and the Lattice Energies

of NH4C1 , NHABr , and NH4I,

Mol. Phys. 21, 761 (1971).

Method used • CLE

Usinq thermo chem i ca 1 cycle the PA is derived

from crystal lattice energy and the distributed

charge on NH4+

.
46 2

H3P | CAS REGN : 7803-51-2

1

1

l P I

Phosphine (8CI9CI)

»

PA (exp) : 200+/-10 kcal/mol Temperature : 298 K

Wendl endt , W . , i Proton Affinity of Phosphine in the Phosphonium Halides,

Science 122, 831 (1955).

Method used ’ CLE

Using thernochemi cal cycle calculate the PA value

from crystal lattice energy.

1 PA (exp) : 156.2+/-3 kcal/mol Temperature :

llada, Y., and Kiser, R. W.»

A Mass Spectrometr i c Study of Some Alkyl-Substituted

Phosphi nes,

J. Phys. Chem. 68, 2290 (1964).

Method used : El

Appearance potential by electron impact of (CH3)3P and (C2H5)3P

Continued on next page
! PA (exp) • 194.5+/-5 kcal/mol Temperature :

Waddi ngton , T . C .

,

Lattice Energies of Phosphonium Bromide and Iodide

and the Proton Affinity of Phosphine,

Trans. Faraday Soc. 61, 2652 (1965).

Method used : CLE

Using thermochemi cal cycle they calculated the PA

from crystal lattice energy and heats of formation.

| PA (exp) : 186 kcal/mol Temperature ‘

Haney, M. A., and Franklin, J L. , Mass Spectrometr i c Determination of the Proton Affinities

of Various Molecules,

J. Phys. Chem. 73, 4328 (1969).

Method used : MS

Delta H estimated 3 5X total translational energy

of the products of RH+ + RH -> RH2+ + R. Continued on next page
GB (exp) : 178.8+/-2 kcal/mol Temperature *• 300 K

PA (exp) ' 187.4+/-2 kcal/mol Temperature : 300 K

Wolf, J. F., Staley, R. H., Koppel, I., Taagepera, M.,

Mclver, R. T., Jr., Beauchamp, J. L.» and Taft, R. W.,

Gas Phase Basicities and Relative Proton Affinities of

Compounds between Water and Ammonia from Pulsed Ion

Cyclotron Resonance Thermal Equilibria Measurements,

J. Am. Chem. Soc. 99, 5417 (1977).

Method used : ICR

Calculated entropy

Equilibrium; scale based on NH3

H4N2 CAS REGH : 302-01-2

1 N**N

Hydrazine (8CI9CI)

PA (exp) • 221 kcal/mol Temperature :

Jen, J. A., and Thomas, T. D.,

Core Ionisation Potentials in Dimethyl Ether and

Methyl Amine,

J. Electron Spectrosc. 4, 43 (1974).

Method used • CIP

Assuming that delta H of CH4 + NH2NH3+ -> CH3NH2 + HH4+ is equal to the difference in

carbon IS ionization potentials of CH4

and CH3NH2

.

CIP = core ionization potential.
46 5

H4S i I CAS REGN s 7803-62-5

SI

I

i

Si lane (8CI9CI)

PA (exp) 155+/-3 keal/mol Temperature •'

Cheng, T. M. H.» and Lampe, F. 11.,

SiH5 + and the Proton Affinity of Monosilane,

Chetn. F hy s . Letters 1 9 , 532 ( 1 973 ).

Method used ’• MS

Bracketing relative to C2H2 AND C3H7.

He I CAS REGN

1 7440-59-7

1 HE

Helium (8CI9CI)

PA (exp) 41.5 keal/mol Temperature ;

Bel'skii, V. E., and Izmailov, R. I.,

Proton Affinity of Atoms and lens,

Zh. Obshch. Khirn. 44, 2297 (1974).

Method used : TC

Using thermochemical cycles.

Continued on next page
466

I PA (exp) : 42 keal/mol Temperature

Beauchamp, J . L . , Interactions between Ions and

Ed. P. Ausloos, (Plenum Press

1975) p. 413.

Molecules,

Now York and London,

Method used : H

E

Lite nature Survey.

Kr

1

[ CAS REGN : 7439-90-9

1 KR

! Krypton (SCI9CI

)

1 1 1

1 1

1 1 PA (exp) • 1 15+/— 15 keal/mol

r

1 Temperature :

1 Munson, M. S. B., and

Reactions of Gaseous

on Ionic Reactions in

J. Am. Chcm. Soc. 87,

Field, F. H.,

Ions. XVI. Effects of Additives

Methane

,

4243 ( 1965)

.

Method used : MS

Bracketing relative to H2 and CM 4.

Continued on next page
46 7

PA (exp) = 100.3+/-0.5 keal/mol Temperature :

Payzant, J. D., Schiff, H. I., and Bohma, D. K .

,

Determination of the Proton Affinity from the Kinetics

of Proton Transfer Reactions. V . The Equilibrium

H3+ + Kr = KrH+ + H2 and the Relative Proton Affinity

of Kr and H2

,

J. Chem. Phys. 63, 149 (1975).

Method used : FAG

Equilibrium relative to H2. Delta 5 estimated

from the entropies of the particles.

Mg | CAS REGN : 7439-95-4

MG

Magnesium (8CI9CI)

PA (exp) : ”198 keal/mol T emperatu r

e

350 K

Po, P. L., and Porter, R. F.

H i gh-Tenperature Ion-Molacule Chemistry. A Kinetic

Study of Gas-Phase Reactions of Magnesium Atoms

with D3+, Methanium, Ammonium, and tert~C4H9+ Ions,

J. Am. Chem. Soc. 99, 4922 (1977).

Method used : MS

Bracketing relative to (CH3)2C ::: CH2 and NH3
468

Mg2

r

CAS REGN : 29904-79-8

Mq + Mq

Magnesium molecule

PA (exp) • 219+/-7 kcal/mol Temperature : 700 K

Po, P. L., and Porter, R. F.

A Thermodynamic Study of the Reactions of Mq+(q)

and MgH+(a) with Magnesium,

J. Phys. Chcm. 81, 2233 (1977).

Method used • MS

Calculated entropy

From the K equilibrium of rection MqH+ + Mq(s) = Mq2H+ and usinq PA (Mq) - 196 and delta Hf(H+) = 365.7
46 9

NO

r

CAS REGN : 10102-43-9

N + + 0

N i troqen oxide (NO) (8CI9CI)

I

PA (exp) : <127 kcal/mol Temperature •

Munson, M. S. B., and Field, F H Reactions of Gaseous Ions. XVI

on Ionic Reactions in Methane,

J. An. Chon. Soc. 87, 4243 (1965)

Effects of Additives

Method used : MS

Bracketing relative to CH4.

PA (exp) : 126.9+/— 1.1 kcal/mol Temperature : 300 K

Hemsworth, R S., Payzant, J. D., Schiff, H. I.,

and Bohne, D. K.,

Rate Constants at 297 K for Proton Transfer Reactions

with NH3 Comparisons with Classical Theories and

Exotherm i c i ty

,

Chem. Phys. Letters 26, 417 (1974).

Method used : FAG

Equilibrium relative to H2. Use PA (H2) from

J. Chem. Phys. 55, 4270 (1971).
47 0

N2 | CAS REGN : 7727-37-9

NSSN

Nitrogen (SCI9CI)

PA (exp) : 112.6+/— 1 kcal/mol | Temperature ' 298 K

Schiff, H. I., and Bohme, D. K.,

Flowing Afterglow Studies at York University,

Int. J. Mass Spactrom. Ion Phys. 16, 167 (1975).

Method used • FAG

Equilibrium scale based on H2. Delta S derived from theoretical

entropies and entropies of iso-electronic particles.

PA (exp) : 130+/-2 kcal/mol Temperature •

Willis, C., Lossing, F. P., and Back, R. A. The Heat of Formation of N2H2 and the Proton Affinity

of N2

,

Can. J. Chcm. 54, 1 (1976).

Method used : EM

The PA i s derived from the appearance potentials of

N2+ and N2H+
I N20 CAS REGN : 10024-97-2

0++N++N

I Nitrogen oxide (N20) (8CI9CI)

PA (exp) : 138. A keal/mol Temperature : 293 K

Schiff, H. I., and Bohrne, D. K. , Flowing Afterglow Studies at York University,

Int. J. Mass Spectrom. Ion Phys. 16, 167 (1975).

Method used : FAG

Calculated entropy

Equilibrium; scale based on CO.

I 02 CAS REGN : 7782-44-7

1 0 + + 0

I Oxygen (8CI9CI)

1 1

1 PA (exp) : 100. 9+/-. 5 keal/mol

t

i Temperature '• 298 K

McCulloh, K. E .

,

To be publ i shed

.

Method used : PI

Photo i on i zat i on of H202.

Continued on next pegs
472

PA (exp) 100.4+/-1.5 keal/mol T emperature 298 K

Kim, J. K., Theard, L. P., and Huntress, W. T., Jr.,

Proton Transfer Reactions from H3 + Ions to N2, 02,

and CO Molecules,

Chem. Phys. Letters 32, 610 (1975).

Method used : ICR

Equilibrium relative to H2. Entropy change estimated from the

known theoretical iso-electronic counterpart entropies of the

spec i es

.

PA (exp) •' 100+/-1 keal/mol Temperature •' 298 K

Fennelly, P. F., Hemsworth, R. S., Schiff, H. I.,

and Eohme, D . K .

,

Determination of the Proton Affinity from the Kinetics

of Proton Transfer Reactions. IV. The Equilibrium

02H+ + H2 = H3+ + 02 and the Relative Proton Affinity

of 02 and H2,

J. Chem. Phys. 59, 6405 (1973).

Method used : FAG

Equilibrium relative to H2. Entropy chanqe estimated from the

known theoretical iso-electronic counterpart

entropies of the species.
473

03S | CAS REGN : 7446-1 1-9

0++S++0

++

0

Sulfur trioxide (SCI9CI)

PA Cexp) : 142+/-2 kcal/mol Temperature '•

Munson, B., Smith, D., and Poll ay, C. The Mass Spectrum, Proton Affinity and Ion-Molecule

Reactions of S03

,

Intern. J. Mass Spectrom. Ion Phys. 25, 323 C1977).

Method used s MS

Bracketing relative to HBr and CO. Use delta Hf(H+) = 366.
CAS REGN : 7440-61-1

Uranium (8CI9CI)

PA (exp) • 233+/-A kcal/mol T emperature A 0 0 K

Armentrout, P., Hodges, R.. Metal Atoms as Superbasas 1 Affinity of Uranium,

J. Am. Cham. Soc. 99, 3162

and Beauchamp, J. L. the Gas Phase Proton

( 1 977 ) .

Method used • MS

Threshold measurement of UD+. Correction for DCUD+)

- DCUH+) assuming delta HAOO = delta H298

Entropy change assumed zero
47 5

Xe | CAS REGN : 7440-63-3

XE

Xenon (8CI9CI)

PA (exp) : 1 18+/— 11 keal/mol Temperature :

Munson, M. S. B., and Field, F. H.,

Reactions of Gaseous Ions. XVI. Effects of Additives

on Ionic Reactions in Methane,

J. Am. Chem. Soc. 87, 4243 (1965).

Method used • MS

Bracketing relative to CH4 and reaction

XE+C2P1/2) + CH4

.

PA (exp) : 1 13.2 + /— 1 .5 keal/mol Temperature • 800 K

Fehsenfeld, F. C., Lindinger, W., Schiff, H. I.,

Hemsworth, R. S., and Bohme, D. K. Determination of the Proton Affinity from the

Kinetics of Proton Transfer Reactions. VI. The

Relative Proton Affinities of N2, Xe, and C02,

J. Chem. Phys. 64, 4887 (1976).

Method used • FAG

Van ' t Hoff plot

Equilibrium relative to N2; scale based on

PA (M2) = 112.6
Gas Phase Basicity Index

47 6 123.0 4 1 153.3 453

154.7 46

156.4 456

162.3 453

162.5 24

164.4 55

165 . 1 47

165.4 108,253

165.7 42,454

165.9 256,455

166.5 33

166.7 20,457

166 .8 5 1,265

166.9 19,267

167.0 267

167.2 22

167.3 54

167.8 270

169.5 96

169.6 13

169.7 43

169.8 65

170.1 60

17 1.2 52 , 83,246

17 1.8 57,66

17 1.9 25

172.0 269

172.2 69

172.3 2 , 116,144

172.4 456

172.5 97

172.7 247

173.0 98

173 . 1 47 , 154,248

173.4 249-250

173.7 25 1 173.9 119,257

174 . 1 252,334

174.2 264

174.3 254

174.4 34,255

174.5 85,266

174.7 269

175 . 1 370

175.4 15 1 175.6 123

176.1 174

176.4 217

176.6 294

176.7 268

177.1 157

177.2 64

177.4 162

177.5 34

177.6 36 1 178 . 1 3 5
Gas Phase Basicity Index

477

178.3 103

178.4 82

178.8 464

178.9 83

179.0 68,114

179 . 1 276

179.2 57 , 329

179.6 333

179.8 67,121

179.9 68

180 . 1 99,336

180 .

2

1 16 180.8 88,335

180.9 326 , 335,370

181.0 132

13 1.1 277

18 1.3 85,360

131.4 19 1 13 1.8 369 , 371,391

18 1.9 134 , 172

182.0 372-373

182.2 339,413

182.4 104 , 177,4 1 1 132.5 190

182.6 390-391

182.7 86

182.8 169,227

132.9 230 , 359,372

133.0 367 , 338 , 412-413

133.2 330,410

133.4 123

133.5 337

183 .

6

159

183.7 122,368

133 .

9

175

134.

1

222

134.2 134

134.4 158

184.5 174

134.7 173,232

185 . 1 162,460

135.4 153

135.3 179

136 .

0

44

186.2 133

136 .

3

327

186 .

5

1 14 136.7 120

186.8 193,295

187.2 373

187 .

4

218

137 .

6

12 1 138.4 352-353

188.5 75

188 .

6

176

138.7 189

188.9 61,328
Gas Phase Basicity Index

478

189.0 17 1 189.2 170

189 .

3

402

189.7 228

189.8 124, 178,325

190.0 190,300

190.2 89

190.3 177

190.4 330

190.5 ISO

190.7 296

190.8 229

19 1.1 225,23

1

191.3 392

191.5 362

191.7 237

19 1.8 308

191.9 62,313

192.1 18 1 192.2 152,309

192.3 22 1 192.5 226

192.9 135,236

193.1 365

193.4 38,278

193.7 279,291-292,421,460

193.9 293

194.0 279,364

194.4 2 19

195.0 76

195.2 194,384

195.3 363

195.5 3 14 195.6 3 12 195.9 37

196.1 1 1 1 196.6 3 15

196.9 385

197.0 274,387

197.2 8 1,220

197.5 72,272

197.7 423

197.8 263

197.9 152

198.0 273

198.4 2 10 198.5 27 1 193.9 297

199.0 147,262

199.5 3 16 199.6 1 10 199.8 26 1 199.9 280

200.2 339,347

200.4 278

200.6 1 05, 108,208

200.7 426
Gas Phase Basicity Index

47 9 200.8 404

200.9 87 , 168

20 1.2 129 , 146,258

201.4 430

20 1.8 80

202.2 259

202.5 260

202.9 36 , 293,437

203.0 366,377

203.2 340-341

2 0 3.4 92,235

203.6 374

203.7 207,213

203.9 167,348

204 .

0

204

2 0 4.5 205

204.6 74

204.7 166

204.8 3 1 1 204 .

9

74

205 .

3

126

205.4 185

205.6 90 , 92,284

205 .

7

37

205 .

9

90

206 . 1 136 , 338

206.4 145,209

206 .

6

331

2 0 6.8 332 , 376,406

207 . 1 139

207.2 206

207 .

3

140

207.6 197

207.7 196

207.8 197

203 .

0

233

203 . 1 137,318

203.2 137,355

208.3 196

208.4 139

208.6 184

208.8 242

203 .

9

200

209.0 242

209.3 141 , 200,386

20 9.4 395

209.5 9 1,93

209.6 234

209.7 91 , 212 , 351 , 355 , 376,417

209.8 2 13

2 10.1 3 10 210.2 195

210.3 2 12 210.4 195

2 10.9 188

2 11.1 239

211.4 287
Gas Phase Basicity Index

480 2 11.7 2 11.9 2 12.0

212.1

212.2 2 12.3 2 15.0 2 13.3

213.6 2 13.7

213.8

214.0

214.1 2 14.3

214.4 2 14.5

214.9

215.5

215.9 2 16.0

216.1 2 16.5

216.7 2 17.0

217.2 2 17.3 2 17.7 2 17.8

217.9 2 18.0 2 18.3

218.4

218.6 2 18.8 2 18.9

219.0

219.1 2 19.9

220 . 0

220 . 5

220 . 6

220 .8 221.1

221.2

221.3

221.4

22 1.7

221.9

222.8

223 . 1 223 . 6

224 . 0

224 . 1 224.6

224 . 9

225.4

226 . 9 , 140

,289

300,407 , 182

,281

,233

,243

,420

,379

,235

,3 17

,3 17

-241

,380

,323 , 321,429 , 323 , 382

239

127

14 1 4 15 127

375

232

182

94 , 138

283

95

198

138

233

193

142

94

40 1 199

320

320

199

285

307

156

378

234

307

424 3 12 240

357 3 1 1 240

398

143

324

245 4 1 9 3 19

354

143

319

356

245

20 1 400

399

399

38 1 322

425

322

35 1 244 4 18
Gas Phase Basicity Index

227.7 358

229.3 383

'

.

.

1 1

.

.

.
Proton Affinity Index

482

41.5 465

42 . 0

466

94 . 3

443

96 . 0 451

97 . 0

450

98.0 44 1 99 . 9 449

100.0 1,472

100.3 467

100.4 472

100.9 47 1 10 1.0 450

10 1.5 450

103.8 442

112.0 443

112.6 470

113.2 475

115.0 3 - 4,466

118.0 475

120.0 440

121.0 17 123.0 42

124.0 4 1 126.0 3 1 126 . 9

469

127.0 30,469

128.0 79

129 . 1 40

130.0 470

130.5 3 1 130.7 40

13 1.4 3 1 131.8 80

134.0 444

138.4 47 1 139.0 19

139.6 79

140.0 440

14 1.0 1 1 142.0 473

142.7 39

143.0 39,130

144.0 9,446

145.0 447

147.0 5 , 18,20

148. 2130

15 1.0 27,445

152.8 13 1 155.0 465

156.2 462

160.0 27

160.6 59

162.0 21

163.0 25

164 . 0 26 , 187

165.0 7 1
Pro-ton Affinity Index

483

165.8 452

166 . 0 49

166.8 187

167.0 49 , 442,451

168.0 42

169.0 22

169.3 453

170.0 22,70

170.3 26,453

17 1.0 69 , 452,455

17 1.6 255

17 1.9 46

172 . 0

10 , 45-46

172.2 55

172.4 456

173.3 47,454

173.6 53

173.9 454-455

17 4.0 23,53

174.5 19-20

174.6 22

174.7 457

17 4.8 48

175 . 0

73

175 . 3456

176.0 100-101

177.0 13

177.1 455

177.4 13

177.5 43

177.7 96

177.9 60

178.0 23,48

178.5 16,246

178.9 24

179.0 12 , 24 , 32,52

179.8 253

180.0 107,276

180 . 1 25 , 144,269

180 . 3

12 , 97 , 247-248

180.4 24 9 180.5 250

180 . 6106 , 257

130.8 93

180 . 9 2 , 47 , 154 , 165

13 1.0 78 , 164

18 1.1 103,252

18 1.2 270

18 1.3 25 1,254

181.4 269

181.6 256

18 1.9 163,264

182 . 029 , 32 - 33,452

182 . 1 33

132.2 34 , 107,266

182.3 265

182.5 265,267
Proton Affinity Index

484

182.6 108 , 267,334

1 S 3 .

2

151 , 160

183.8 334

184.0 5

1

, 63,87

184.2 217

184.4 294

184.5 54

134 .

9

157

185.0 64-65

185 .

3

34

135.4 65,361

185.

9

35

186.0 56 , 63 , 77 , 82,463

186 . 1 103

186 .

2

82

136 .

7

83

136.3 23,83

187 .

0

8 , 57 , 68,115

137 .

4

57 , 333,464

187.5 333

187 .

7

68

187.3 69

137 .

9

99 , 1 16,336

133.0 66-67 , 1 13 ,

1 16 133.2 66

133.3 99

183.5 277

188.6 335

183.7 326,335

183.8 132

139.0 58 , 84 , 133,372

189 . 1 85 , 360, 370

189.3 85 , 88, 191

189 .

4

64

189.5 56

139 .

6

334,37 1 139.7 134 , 172,373

189.8 150 , 359,372

190.0 84 , 1 15 , 132 , 367,391

190.1 86

190.2 104

190.3 30

190.4 389 , 391,413

190.6 169 , 227 , 370,41

1

190.8 4 13

190.9 175

19 1.1 1 19 , 122,368

19 1.2 123 , 159

19 1.4 159

19 1.7 174

19 1.9 222

192.0 109 , 13 1 , 134 , 192

192.1 173

192.2 158,268

192.3 174

192.5 232

192.6 16 1
Proton Affinity Index

485

193.0 6 193.2 153, 179

193.3 86

193.5 162,224

193.6 1 12

193.7 161,170

193.8 1 14 193.9 1 14 194.0 102 , 117 , 120 , 122 , 133 , 173 , 192,459

194.1 50 , 120,327

194.2 162

194.4 223

194.5 463

194.6 193 , 276,373

194.7 14,329

195.0 295

195.2 2 18

195.4 121

195.7 1 12 195.9 50,225

196.0 113,176

196.1 189,304

196.4 171,305

196.6 352

196.7 328

197.0 62 , 1 18 , 125 , 170 , 176 , 178,458

197.1 228,402

197.2 124

197.3 190,224

197.4 190,300

197.6 89 , 178,325

197.7 303

197.9 6 1 198.0 177 , 189,467

198.1 177

198.2 306,330

198.3 180

198.4 392

198.5 225

198.6 229

198.7 330

198.8 350

198.9 231

199.0 7 , 35,337

199.3 313,362

199.5 237

199.6 308

199.9 18 1 200.0 202 , 230 , 309,462

200 .1 221,230

200.3 62,226

200.4 14 200.7 135,236

20 0.9 365

201.0 210

20 1.7 298

2 0 1.8 38,364
Pro-ton Affinity Index

486

202.2

202.3

202.6

2C2.8

203.0

203 . 1 203.3

204.0

204 .

3

204.5

204.6

204.7

205.0

205.2

205 .

3

205.4

205 .

6

205.7

205 .

9

206 .

0

206 .

2

206.4

206.3

206 .

9

207 .

0

207 .1 207.6

207.8

208.0

208 . 1 208.3

208.4

208.6

203.7

208.8

2 CS . 9 209.0

209.2

209.4

2 10.0

2 10.2

2 10.3

2 10.4

210.6

2 10.8

2 11.0

211.2

2 11.3

2 11.5

211.6

2 11.8

2 12.3

2 12.4

2 12.8

2 13.0

213.1

213.7

219

460

194

76

312,384

363

314

299.315

1 1 1 81,111

220

385

423

337

46 1 274

263

75,461

72 , 152,272

459

210

147 , 273,453

8 1,262

271.316

21 , 148 - 149 , 203 , 216 , 393 , 397 , 414,422

260,297

26 1

1 10 403,459

426

15,87

208

146,404

163

278

278,280

15 , 105 , 108 , 129,258

430

152

259

80

260

377

136

366

36,439

235,279

36

207

340-342

204

167 , 205,348

166

74

75

37

37 , 126
Proton Affinity Index

487

213.8 145,284

213.9 186

214.0 90,349

214.2 209

214.3 90

214.4 331

214.5 338

214.6 332,406

2 15.0 206,2 1 1 215.5 139

215.7 140

216.0 197

216.2 197

216.4 238

216.5 94 , 137 , 318,355

216.6 137

216.7 196

216.3 184,301

217.1 386

217.2 242,286

217.3 93

217.4 242 , 339,347

217.6 213

217.7 91,200

217.9 91

218.1

212

218.5 310

218.6 195

218.8 195

218.9 188

219.0 468

219.2 287

219.4 128

219.5 239

219.8 283

22 0.0 127 , 155,2 14-2 15 , 275 , 375 , 427,43 1 - 436,438

220.1 127 , 239,375

220.2 141

220.4 140

220.5 183

220.6 92

220.8 282,374

220.9 213

221.0 141 , 394,464

221.1 239

221.4 407

221.5 138,182

221.6 283

221.8 300

221.9 182

222.0 290 , 311 , 396 , 405 , 409,428

222.1 133 , 281,408

222.3 198

222.6 233

222.7 198

223.1 233

223.3 142,401
Pro-ton Affinity Index

488

223.5 346

223.8 199

223 . 9420

224.0 376

224.2 243

224.3 320

224.5 199,345

224.7 320

224.8 2 S 5 225 . 1 156 , 235,343

225.4 379

225.5 308

225 . 6

139,234

225.8 424

225 . 9307,378

226 . 1 312 , 317,344

226.2 240

226 . 3

302

226.4 357

226 . 6 3 11, 3

17,395

226.7 240-24 1 226.8 234,398

227.5 94

227.7 324

227 . 9 4 16 223 . 1 380

223 . 3

419

228.4 319 , 321,429

228.6 354

229 . 0 3 19

229 . 1 356

229 . 3 4 15

229 . 9

332

230 . 1 400 2 3 0.6 3 S 9 230 . 9

399

231.4 33 1 231.6 143

232.0 425

232.4 322

232.7 35 1 234.6 245

235.0 323

235 . 1 143,245

235.4 323

236.6 20 1 238 . 0

474

241.6 448

248 . 5449

263.5 443

27 0 .1 44 1
CAS Registry Number Index

489

50 - 00-0 21-22

50 - 89-5 4 14

57 - 14-7 93

58 - 61-7 409

58 - 96-8 393

60 - 29-7 189-190

60 - 35-5 75

62 - 53-3 278-280

64 - 17-5 82-83

64 - 13-6 23-25

64 - 19-7 66-67

65 - 46-3 396

65-7 1-4 2 16 66 - 22-8 149

67 - 56-1 32-34

67 - 63-0 131-132

67 - 64 - 1 112-114

67 - 68-5 87

68 - 12-2 129

68 - 94-0 2 1 1 71 - 23-8 132-133

71 - 30-7 155 7 1 - 36-3 19 1 71 - 43-2 269-270

73 - 24-5 214

73 - 40-5 2 15

74 - 82-8 30-3 1 74 - 83-9 25

74 - 84-0 79-30

74 - 85 - 1 59

74 - 87-3 26-27

74 - 88-4 28

74 - 89-5 36-37

74 - 90-8 19-20

74 - 93-1 34-35

74 - 96-4 69

74 - 98-6 130-131

74 - 99-7 100

75 - 00-3 70

75 - 02-5 53

75 - 03-6 73

75 - 04-7 90

75 - 05-8 56-57

75 - 07-0 63-65

75 - 08-1 88

75 - 10-5 20

75 - 15-0 42

75 - 18-3 89

75 - 19-4 106

75 - 21-8 65

75 - 31-0 137

75 - 33-2 134

75 - 38-7 48

75 - 46-7 18

75 - 50-3 138-139

75 - 52-5 29

75 - 64-9 195
CAS Registry Number Index

A 90

75-65-0 192

75-66-1 193

75-73-0 17 75-89-8 55

75-97-8 308

76-05- 1 46-47

78-81-9 196

78-SZ-O 158

78-84-2 169

78-93-3 170

79-09-4 1 19

79-1 1-8 51

79-20-9 120-121

79-24-3 77

87-42-3 203

87-85-4 423

90-04-0 347

91-66-7 4 15

93-58-3 365

95-47-6 367-368

95-54-5 29 1 96-22-0 225

96-47-9 226

98-06-6 410-41 1 98-82-8 388-389

93-83-9 387

98-86-2 363

98-95-3 268

100-41-4 369-37 1 100-42-5 362

100-46-9 333

100-47-0 329

100-48- 1 26 1 100-52-7 330

100-54-9 262

100-6 1-8 339

100-66-3 337

100-70-9 263

100-76-5 354-355

102-54-5 403

102-69-2 399

102-70-5 398

102-82-9 425

103-65-1 390-391

103-69-5 374

104-51-8 412-413

104-87-0 364

104-88- 1 325

104-94-9 348

105-07-7 36 1 106-42-3 372

106-47-8 27 1 106-49-0 340

106-50-3 292

106-97-8 187

106-98-9 160

107-03-9 134
CAS Regi stry Number Index

A 9 1 107-10-8 107- 1 1-9

107-12-0

107-13- 1 107-14-2

107-15-3

107-31-3

107-

47-1

108-

18-9

108-20-3

108-38-3 1 03-42-9 1 OS-44- 1 1 08-45-2 1 03-47-4

103-43-5

103-67-3

103-88-3

103-89-4

103-90-7

108-91-8

103-94-1

108-

95-2

103-99-6

109-

06-8

109-09-1

109-55-7

109-60-4

109-73-9

109-74-0

109-76-2

109-77-3

109-85-3

109-89-7

109-94-4

109-97-7

109-99-9 1 10-00-9 1 10-18-9 1 10-53-7 1 10-59-3 1 10-60-1 1 10-62-3 1 10-74-7 1 10-85-0 1 10 - 86 - 1 1 10-89-4 1 10-91-S 1 10-95-2 1 10-96-3 1 1 1-18-2 1 11-26-2 1 1 1-43-3 1 1 1-47-7 1 1 1-5 1-3 1 1 1 - 68-2 1 1 1-92-2

139-140

126

104

99

47

94

67-69

377 3 17 3 12 373

272

341-342

293

343

344

392

333-336

28 1 264-265 3 10-3 1 1 299

276

282

233

204

244

230

197

159

143

96

14 1 193

122-123

152

17 1 150

322

238

222

20 1 227

173-174

183

212-213

233-234

184

353

378 4 18 3 18 3 13 3 15

383

355

379
CAS Registry Number Index 4 92 1 15 - 07 - 1 115 - 1 0-6

115 - 11-7 1 15 - 20-8 1 1 9-6 1-9

120 -

94-5

121 -

44-8

121 - 69-7

121 -

72-2

122 -

39-4

123 - 1 1-5

123 - 33-6

123 - 39-7

123 - 54-6

123 - 72-8

123 - 75-1

123 -

91-1

124 -

02-7

124 - 09-4

124 - 38-9

124 - 40-3

127 - 19-5

141 -

78-6

142 -

68-7

142 - 84-7

144 - 49-0

151 - 18-8

151 - 56-4

275 - 51-4

230 - 57-9

239 - 80-5

289 -

95-2

290 -

37-9

302-0 1-2

327 - 54-8

334 - 88-3

350 - 03-8

350 - 40-3

352 -

93-2

353 -

56-6

359 - 1 1-5

359 - 13-7

362 - 43-6

362 -

76-5

363 -

72-4

367 - 1 1-3

367 - 23-7

367 -

64-6

368 -

48-9

37 1 - 40-4

372 - 18-9

372 - 19-0

372 - 38-3

372 - 47-4

372 - 48-5

383 - 63 - 1 333 - 66-4

107-108

84-86

161-162

52

426

234-235 3 19

375-376

394

42 1 366

115-116

76

220

172

182

175

300

323

40-42 9 1-92

185

176-177

228

320

541 1 1 74-75

40 1 307-308

145

146

147

464

248 2 1 33 1 385

194 7 1 45

60

422

428

247

254

25 1 294

258

273

255-256

274

252-253

207

203

15 1 2 17
CAS Registry Number Index

493

392 - 56-3

400 - 59-9

406 - 34-8

430 -

67-1

431 -

47-0

455 -

19-6

456 -

48-4

459 -

57-4

460 -

39-9

46 1 - 24-5

462 - 06-6

462 -

94-2

463 -

49-0

463 - 51-4

493 - 66-8

503 - 29-7

503 - 30-0

506 - 68-3

506 - 77-4

513 - 35-9

530 - 48-3

536 - 90-3

540 - 36-3

540-6 1-4

540 - 67-0

542 - 76-7

545 - 06-2

547 - 63-7

550 -

33-4

551 -

62-2

554 - 12- 1

556 - 61-6

556 -

64-9

557 -

01-7

557 - 40-4

563 - 46-2

563 - 80-4

563 - 83-7

585 - 43-8

589 -

93-5

590 -

18- 1

591 -

22-0

591 -

49-1

592 -

84-7

593 -

53-3

593 - 54-4

593 -

88-4

594 -

09-2

594 - 1 1-6

594 - 39-8

598 - 56-1

598 - 98- 1

603 - 34-9

613 - 97-8

616 - 12-6

616 - 38-6 6 16 - 39-7

246

298

80

72

97

360

327

328

108

157

266-267

245

10 1 50

350

127 1 17 1213

223

430

34 9 257

62

133

103

43

23 1 405

249

178

53

58

148

300

224-225

229

186

429

345

163

346

352

232

27

331 36

142

164

239

199

309

437

395

304

124

240
CAS Registry Number Index - 494 6 16 - 47-7 156

620 - 08-6 285

623 - 49-4 154

623 - 53-0 18 1 624 - 64-6 165

624 - 78-2 140 -14 1 624 - 89-5 135

624 - 91-9 30

625 - 27-4 305

625 - 54-7 236

625 - 55-8 179

625 - 58 - 1 78

625 - 80-9 3 16 626 - 23-3 380

626 - 60-8 205

626-6 1-9 206

626 - 67-5 3 1 1 -3 12 630 - 08-0 39

637 - 92-3 3 14 676 - 59-5 92

677 - 41-8 109

687 - 48-9 235

693 - 86-7 2 18 693 - 89-0 295

694 - 52-0 209

694 - 85-9 286

715 - 91-3 408

753 - 90-2 6 1 -i62

763 - 29 - 1 306

765 - 43-5 219

765 - 47-9 353

819 - 06-7 166

819 - 46-5 167

918 - 02-5 32 1 926 - 64-7 168

931 - 20-4 30 1 996 - 35-0 24 1 1072 - 44-2 128 1 122 - 54-9 332 1 122 - 58-3 35 1 1 122-6 1-8 2 10 1 124 - 18 - 1 326 1 1 90 - 79-0 183 1 195 - 32-0 404

13 10 - 5 S -3 448

1310 - 65-2 448

1310 - 73-2 449

1333 - 74-0 449 --45 1 1528 - 30-9 296

1534 - 08-3 1 18

1605 - 72-7 14 - 15

1628 - 89-3 287 --288

1630 - 77-9 49

1630 - 78-0 49

1634 - 04-4 237

1683 - 88 - 1 144

17 12 - 69-2 4 o 4
CAS Registry Number Index

495

1712 - 70-5 384

1733 - 57-9 431

2004 - 03-7 275

2016 - 57-1 4 17 2085 - 66-7 400

2129 - 89-7 427

2154 - 59-8 16 2168 - 84-5 125

2367 - 82-0 250

2450 - 71-7 105

2551 - 62-4 446

2730 - 67-8 1 10 2781 - 85-3 102

2868 - 37-3 22 1 2959 - 75-3 432

3796 - 23-4 259

3796 - 24-5 260

4096 - 20-2 420

4096 - 21-3 407

4143 - 41-3 8 1 4233 - 13-0 435

4252 - 88-4 433

4363 - 25- 1

419

4458 - 31-5 356

4663 - 22-3 297

5500 - 21-0 153

56 16 - 32-0 1 1 1 5627 - 05-4 397

5313 - 64-9 242

6569 - 51-3 7 6921 - 27-3 277

6921 - 28-4 234

6921 - 29-5 386

7037 - 68-5 38 1 7295 - 76-3 289

7439 - 90-9 466

7439 - 95-4 467

7440 - 37-1 1 7440 - 59-7 465

7440 - 61-1 474

7440 - 63-3 475

7440 - 70-2 439

7446 - 1 1-9 473

7637 - 07-2 4 7647 - 01-0 440

7664 - 39-3 443

7664 - 41-7 458

7727 - 37-9 470

7732 - 18-5 45 1 7782 - 39-0 44 1 7782 - 44-7 47 1 7783 - 06-4 454

7783 - 07-5 457

7783 - 54-2 445

7784 - 42 - 1 2

7789 - 20-0 442

7803 - 51-2 462

467

466

46 1 453

442

472

456

464
CAS Registry Number Index

A 96

7803-62-5 465

10024-97-2 47 1 10034-85-2 447

10035-10-6 1 1 10076-31-0 357

10102-43-9 469

120 07-7 1-5 8

12061-70-0 444

13463-40-6 202

13709-83-6 3

13952-84-6 200

13960-3C-0 95

17222-37-6 44

18 132-40-6 324

18283-93-7 9 19237-45-7 5 1 9624-22-7 10 1996 1-27-4 243

21351-79-1 44 1 21931-37-3 382

22025-87-2 424

23662-75- 1 290

25493-13-4 359

29904-79-8 463

31023-92-4 4 16 32042-33-9 98

38103-96-7 180

53687-79-9 302

55 186-75-9 402
Molecular Formul A r A sH3

BF2H

BF3

B2H6

B3H5N3

B3H6N3 B AH8

BAH 10 35H9

BrH

CBrN

CC1H

CC 1 2

CF2

CFA

CHF3

CHN

CH2F2

CH2N2

CH20

CH202

CH3Br

CH3C1

CH3F

CH 3 1

CH3N02

CHA

CHAO

CH AS

CH5N

CH5P

CO

C02

CS 2 C2C13N

C2D60

C2HF3

C2HF302

C2H2C1N

C2H2F2

C2H20

C2H3C102

C2H3C1 30

C2H3F

C2H3F02

C2H3F30

C2H3N

C2H3NS

C2HA C2HAF20

C2HAF3N

C2HAN2

C2HA0

C2HA02

C2H5Br

C2H5C1 - A 97 a Index 123A56789101 1 12

13

1A- 15

1617181 9-20

20

21

21-22

23-25

25

26-27

27

28

29-30

30-3 1 32-3A

3A-35

36-37

38

39

A0-A2 A 2 A3

AAA 5 A6-A7

A7

A8-A9

505 1 52

535 A 55

56-57

53

59

606 1-62

62

63-65

66-69

69

70
Molecular Formula Index 4 98

C2H5F 7 1 C2H5F2N 72

C2H5I 73

C2H5N 74-75

C2H5N0 75-76

C2H5N02 77

C2H5N03 78

C2H6 79-80

C2H6FN 80

C2H6N2 8 1 C2H60 82-86

C2H60S 87

C2H6S 88-89

C2H7N 90-92

C2H7P 92

C2HSN2 93-94

C3D9N 95

C3H2N2 96

C3H3F302 97-98

C3H3N 99

C3H4 100-1

C3H4C1N 103

C3H5N 104- 1 C3H6 106-1

C3H6F3N 108- 1 C3H6N2 1 1 1 C3H60 112-1

C3H60S 1 18

C3H602 * 119-1

C3H603 124

C3H6S2 125

C3H7N 126-1

C3H7N0 129

C3H8 130-1

C3H80 13 1-1

C3H8S 134- 1 C 3 H 9 A s 136

C3H9N 137- 1 C3H9N0 14 1 C3H9P 142

C3H 1 0N2 143

C4H4F402 144

C4H4N2 145-1

C4H4N20 148

C4H4N202 149

C4H40 150

C4H5F302 15 1 C4K5N 152- 1 C4H5N02 154

C4H5N30 155

C4H6N2 156

C4H7F30 157

C4H7N 158- 1 C4H8 160-1

C4H8F3N 166-1

C4H8N2 168

C4H80 169-1

02

05

08

10

17 23

283 1 33

354 1

47

53

59

65

67

72
Molecular Formula Index 4 99

C4H802

C4H802S

C4H803

C4H9N

C4H9N0

C4H10

C4H10N2

C4H 100

C4H10S

C4H 1 IN C4H 1 2N2

C5Fe05

C5H3C1N4

C5H4C1N

C5H4FN

C5H4N202

C5H4N40

C51I5N

C5H5N5

C5H5N50

C5H6N202

C5H7F302

C5H8

C5HS0

C5H802

C5H9N

C5H 10 C5H100

C5H 1002

C5H 1 IN C5H 1 1 N02

C5H 120

C5H 13N

C5H 1 4N2

C6F6

C6HF5

C6H2F4

C6H3F3

C6H4F2

C6H4F3N

C6H4N2

C6H5C1

C6H5F

C6H5N02

C6H6

C6H6C1N

C6H6FN C 6 H 6 N 4 C6H60

C6H7N

C6H7N0

C6H7N50

C6H8N2

C6H9F302

C6H10

C6H10F3NO

C6H 1 0 0

173- 179

ISO

181

182- 183

184- 186

187

188

189- 192

193- 194

195- 200

20 1 202

203

204-206

207-209 2 10 21 1 212-213 2 14 2 15 2 16 2 17 2 13

219

220-221

222

223-225

225-229

230-232

233-235

235

236-237

238-243

244-245

246

247

248-250

251-253

254-257

258-260

261-263

264-265

266-267

263

269-270

271-272

273-274

275

276-277

278-284

285-289

290

291-293

294

295-297

298

299-300
Molecular Formula Index - 500

C6H 1 IN C6H 1 1 NO

C6H12

C6H 1 2N2

C6H 120

C6H 1202

C6H13N

C6H 1 40

C6H 14S

C6H15N C 6 H 1 6 N 2 C6 H 1 7 NS i

C7H5C10

C7H5D3

C7H5F0

C7H5N

C7H60

C7H7N0

C7HS

C7H80

C7H9N

C7H9N0

C7H 10 C7H10N2

C7H 12 C 7 H 1 3 N C7H17N

C7H 18N2

C8H4D6

C8H5F30

C8H5N0

CSH8

C8H80

300

301-302

303-306

307-308

308

309

310-312

312-314

315-316 3 17-32 1 322-323

324

325

326

327-328

329

330

331-332

333-336

337

338-346

347-349

350

35 1 352-353

354-

355

355-

357

358

359

360

36 1 362

363-364

C8H802

C8H 10 C8H 1 IN C8H 1 8 S C8H 1 9N

CSH20N2

C9H9C1

C9H9F

C9H9N

C9H 10 C9H 12 C9H 12N206

C9H 13N

C9H 13N305

C9H14N206

C9H 15N

C9H2 IN C10H8

C10H9F3 C 1 OH 1 0 Fe

C10H12

C10H12N404 C 1 OH 120

C10H13N

365-366

367-373

374-376

377

378-382

383

384

385

386

387

338-392

393

394-395

396

397

398

399-400

40 1 402

403

404

405

406

407
Molecular Formula Index

C10H13N5 C 10H 13N504 C 1 0 H 1 <+ C10H14N205

C10H15H

C10H19N

C10H23H

C10H24N2

Cl 1H13H

Cl 1H15N

C12H 1 IN C12H16N206 C 12H 18

C12H19N

C12H27N

C13H 100

C13H130P

C13H17N505

C13H2 IN C14H12

C14H150P

C15H 17CP

C16H190P

C17H210P

C18H15N

C22H3 1 OP

Ca

C1H

CsHO

D2

D20

FH

F0

F3N

F6S

HI

KKO

HL i 0

HNaO

H2

H20

H2S

H2Se

H3N

H3P

H4N2

H4S i HeK r Mq

Mq2

NO

N2

N20

02

OSS U - 50 1 408

409

410-413 4 14 4 15 4 16 4 17 4 18 4 19

420

42 1 4 22

423

424

425

426

427

428

429

430

43 1 432-433

434-435

436

437

438

439

440

44 1 44 1-442

442

443

444

445

446

447

443

443

449

449-45 1 451-453

454-456

457

453-46 1 462-464

464

465

465-

466

466-

467

467

468

46 9 470

47 1 471-472

473

474
Molecular Formula Index

- 502 - Xe

'

475

.

'

'

-

'
Name Index

503

Acetaldehyde (8CI9CI) 63-65

Acetamide (8CI9CI) 75

Acetamide, N-butyl-2 , 2 , 2~tr i f luoro- (8CI9CI)

Acetamide, N , N-di methyl- (8CI9CI) 185

Acetdi methylami de 185

Acetene ^9

Acetic acid (8CI9CI) 66-67

Acetic acid amide 75

d ethyl ester (8CI9CI) 176-177

d, chloro- (8CI9CI) 51

ethyl ester 176-177

fluoro- (8CI9CI) 54

methyl ester (8CI9CI) 120-121

propyl ester (8CI9CI) 230

thio-, S-methyl ester (8CI) 118

trifluoro- (8CI9CI) 46-47

tr i f luorotr i f luorotr i f luorotr i fluorotrifluoro-,

63-65

176-177

298

Acetic

Acet i

c

Acetic

Acetic

Acetic

Acet i

c

Acet i Acet i Acet i Acet i Acet i Acet i Acet i Acet i A c c t i Acet i

ac

ac

ac

ac

ac

ac

acac

ac

ac

acac

acac

d,

d , d,

d,

d , d,

d,

d

,

d

d , d,

a 1 dehyde

ether

butyl ester (8CI9CI)

ethyl ester C3CI9CI)

methyl ester (8CI9CI)

propyl ester (8CI9CI)

2-f luoroethyl ester (8CI)

din 176-177

Acetimidic acid 75

Acetoacetone

Acetone (8CI

)

Acetoni tr i le

Acetoni tri le,

Acet on i t r i 1 e

,

Acetonitri le.

Acetonitrile,

Acetoni tri le,

Acetophenon

Acetophenone

3-Aceto pyridine

Acetoxyethane

1-Acetoxypropane

Acetylacetone

Acetylbenzene

Acetylcyclopropane

.beta. -Acetyl py rid

3-

Acetyl pyridine

4-

Acetyl pyridine

Acrylon 99

Acryloni tri le (8CI)

Ade 214

Adenine (8CI) 214

Adenine riboside 409

Adenine, 9-cyclopentylAdeni ni mi ne 214

. beta

.

-Adenosi ne 409

. beta. -D- Adenosine

Adenosine C8CI9CI)

Aethylis 70

Aethylis chloridum

Ae-tznatron 44 9

220

112-114

(8CI9CI) 56-57

( d i methy lam i no ) - (8CI9CI) 168

(methylami no)- (8CI9CI) 111

amino- (8CI9CI) 62

chloro- (8CI9CI) 47

tri chloro- (8CI9CI) 43

363

( 8CI

)

363

33 1 176- 177

230

220

363

2 19 ne

33 1 332

33 1

99

( 8CI )

409

409

70

408

294

151

97

2 17 144
Name Index

504

.beta.-Alaninenitri le

Alcohol 82-83

Alcohol anhydrous

Alcojel 131-132

Alcosolve 2 131-132

A lora i n 82-83

Allene (8CI) 101

Allyl ether (8CI)

Allyl amine (8CI) 126

sym-Allylene 101

Allylene 100

Aninic acid 23-25

3-Ami no-1-(dimathy lam i no)propane

3-

Am i no- 1 -propene 126

6 - Am i no- 1 H-pu r i ne 214

4-

Am i no-2 ( 1 H

) -py r i m i d i none 155

4-Ami no-2-hydroxypyri mi dine 155

1

Am i no-2-methoxybenzene 347

2-

Ami no-2-methyl butane 239

1-

Ami no-2-methylpropane 196

2-

Ami no-2-methylpropane 195

1-Ami no-3-(dimethylami no)propane

1-Ami no~3-di methylami nopropane

1 - Ami no-3-methoxyben zene 34 9 1-Ami no-3-methy lbenzene 341-342

6-Amino-3H-purine 2 14 1-Amino-4-chlorobenzene 27 1

1 - Am ino-4-methy lbenzene 340

2-Ami no-6~ hydroxypurine 2 15 6-Amino-9-cyclopentylpurine 408

6-Amino-9H-purine 2 14

Aminoacetonitri le 62

m-Ami noan i 1 i ne 293

p-Ami noan i 1 i ne 292

2-Aminoani line 29 1 3-Ami noan i 1 i ne 293

4-Aminoaniline 292

m-Ami noan i sole 349

o-Aminoani sole 347

p-Aminoanisole 348

2-Aminoani sole 347

3-Aminoanisole 349

4- Ami noani sole 348

Ami nobenzene 278- 280

1-Ami nobutane 197

2- Ami nobutane 200

m-Ami nochlorobenzene 272

p-Ami nochlorobenzene 27 1 Ami nocyclohexane 3 ID- 3 1 1 1-Ami nodecane 417

Am i noethane 90

1 -Am i noethane 90

2-Ami noethyl methyl ether 14 1 .beta. -Ami noethylami ne 94

1-Ami noheptane 355

Ami nohexa hydrobenzene 3 10-3 1 1

1 - Am i nohexane 3 18

1 1 1 82-83

300

244

244

244
Name Index

2- 505

Ami nohypoxanthi ne 215

2~Ami no i sobutane 195

Ami nomethane 36-37

1-Ami nopentane 238

Aminophen 278-280

3-

Ami nopheny Imethane 341-342

1-

Ami nopropane 139-140

2-

Ami ncpropane 137

3-

Am i nopropanen i t r i 1 e 111

3-Ami nopropene 126

.beta.-Aminopropionitri le

Ami nopropi on i tr i le 111

3-Aminopropionitrile 111

3-Ami nopropylene 126

6-Aminopurine 214

. alpha . -Ami notoluene 338

. omeqa . -Am i no to luene 338

m-Ami notoluene 341-342

p-Ami notoluene 340

3-

Ami notoluene 341-342

4-

Ami notoluene 340

Ammonia (3CI9CI) 458-461

Ammonia gas 458-461

1 1 1

n-Arnylam i ne 238

tert- Amyl ami ne 239

Amylami ne 238

Arnylene 223

Anaesthetic ether

Anesthesia ether

Anesthetic ether

Anhydrol 82-83

Anhydrous hydriodic acid 447

Anhydrous hydrobromic acid 11 Anhydrous hydrochloric acid 440

Anhydrous hydrofluoric acid 443

189-190

189-190

189-190

Aniline ( 8CI ) 278-280

Aniline, rn-chloro- (SCI

)

272

Aniline, m-f luoro- (SCI

)

274

An i line, o- ter t-buty 1 -N , N-di methyl- (8CI)

Aniline, p-chloro- ( 8CI

)

27 1 An i line, p-fluoro- ( 8CI ) 273

A n i line. N-ethy 1

(SCI ) 374

Aniline, N-ethyl-N -methyl

(8CI ) 395

Aniline, N-methyl- (SCI ) 339

An i line, N , N-d i ethyl- (SCI) 4 15

A n i line. N , N-di methyl- (8CI) 375-376

An i 1 i nobenzene 42 1 An i 1 i noethane 374

An i 1 i nomethane 339

Animal coniine 245

4-Ani saldehyde 366

p- An i sa 1 dehyde (SCI) 366

p-Anisic aldehyde 366

4-Anisidine 348

m-Anisidine (8CI) 349

o-Anisidine (8CI) 347

p-Anisidine (8CI) 348

424
Name Index

506

An i sole (8CI) 337

Anisole, p- i sopropeny 1- (8CI> 406

m-An i sylami ne 349

p-Anisy lamina 348

An i zol 337

[6]Annulene 269-270

Anodynon 70

Anon 299

Anone 299

Ant i ren 188

Antisal la 333-336

Anti sal 2b 443

Anyvim 278-280

Arcton 0 17 Arcton 1 18

A rag i nal 122-123

Argon CSCI9CI) 1 Argon-40 1 Arsenic hydride 2 Arsenic hydride (AsH3) 2 Arsenic trihydride 2 Arsen i uretted hydrogen 2 Arsenous hydride 2 Arsine (8CI9CI) 2 Arsine, trimethyl- (8CI9CI) 136

Artie 26-27

Artificial Almond Oil 330

Ascarite 449

Atomic helium 465-466

Aubepine 366

Avantin 131-132

Avantir.e 131-132

1-Aza~2 , 4-cyclopentadi ene 152

Azabenzene 212-213

1 - Azabi cyclo [ 2 . 2 . 2 ] octane (9CI) 354-

1-

AzabicycloC3.3.3lundecane (9CI)

Azacyclobutane 127

Azacycl ohexane 233-234

Azacyclopentane 182

Azacyclopropane 74-75

Azete, tetrahydro- 127

Azetidine (8CI9CI) 127

Azi methylene 2

1

Azine 212-213

Azi ran 74-75

Aziridine (9CI) 74-75

Aziridine, 1-methyl- (8CI9CI) 128

Azole 152

Azol i di ne 182

trans-Azomethane 81

Azomethane, (E)- (8CI) 81

Azulene (3CI9CI) 401

AAN 62

2-

AB 200

Ba 35846 281

Benzaldehyde (8CI9CI) 330

Benzaldehyde FFC 330

355

4 16
Name Index

507

Benzaldehyde

Benzaldehyde

Benza 1 dehyde

Benzaldehyde

Benzaldehyde

Benzaldehyde

Benza 1 dehyde

Benzaldehyde

Benza 1 dehyde

Benzaldehyde

Benzenam i ne Benzenami ne,

Benzenam i ne

,

Benzenami ne,

B enzenam i ne

,

B enzenam i ne

,

Benzenami ne Benzenami ne,

Benzenami ne Benzenami ne,

Benzenam i ne,

, m-fluoro- (8CI) 327

, p-chloro- (8CI) 325

, p-cyano- 361

, p-fluoro- (8CI) 328

, 3-fluoro- (9CI) 327

, 4- ( tr i f luoromethyl )- ( 9CI

)

360

, 4-chloro- ( 9CI

)

325

, 4-fluoro- (9CI) 323

, 4-methoxy- (9CI) 366

, 4-methyl- (9CI) 364

(9CI) 278-280

hexahydro- 310-311

N-ethyl- (9CI) 374

N-ethyl-N-methyl- (9CI) 395

N-methyl- (9CI) 339

N-phenyl- (9CI) 421

N , N~d i ethyl - (9CI) 4 15

N,N-dimethyl- (9CI) 375- 376

N , N-di phenyl- (9CI) 437

N , N , 3- tr i methyl - (9CI) 394

2~( 1, 1-dimetliylethyl)- N , N-di methy

1

Benzenamine, 2-methoxy- (9CI) 347

Benzenamine, 3-chloro- (9CI) 272

Benzenamine, 3-fluoro- (9CI) 274

Benzenamine, 3~methoxy- (9CI) 349

Benzenamine, 3-methyl- C9CI) 341-342

Benzenamine, 4-chloro- (9CI) 271

Benzenamine, 4-fluoro- (9CI) 273

Benzenamine, 4-methoxy- (9CI) 348

Benzenamine, 4-methyl- (9CI) 340

Benzene (8CI9CI) 269-270

C9CI)

Benzene

,

Benzene

,

Benzene

Benzene

Benzene,

Benzene

Benzene,

Benzene

,

Benzene

Benzene

Benzene,

Benzene,

Benzene,

Benzene

,

Benzene

,

Benzene

Benzene

Benzene

,

Benzene

Benzene

Benzene

Benzene

Benzene

,

Benzene

,

Benzene

,

Benzene

( phenylami no ) - 421

(

1 -methyl ethenyl ) - (9CI)

C

1 -methylethyl ) - C9CI) 388-

( 1 , 1-dimethylethyl )- (9CI)

amino- 278-280

benzoyl- 426

butyl- (8CI9CI)

chloro- (8CI9CI)

cyano- 329

ethenyl- ( 9CI

)

ethyl- (8CI9CI)

fluoro- (8CI9CI)

hexafluoro- (8CI9CI)

hexamethyl- (8CI9CI)

m-difluoro- C8CI)

412-413

264-265

362

369-37 1 266-267

246

423

255-256

methoxy- ( 9C I

)

methyl- (9CI)

methy l-d3-

337

333-336

326

387

389

410-41 1

nitro- (8CI9CI) 268

o-di fluoro- (8CI) 254

p-d i fluoro- (SCI) 257

pentaf luoro- (8CI9CI) 247

propyl- (8CI9CI) 390-391

tert-butyl- (8CI) 410-411

1 -( di methy lami no ) -3-methyl - 394

1-(1-methylethenyl)-4-(trifluoromethyl)- ( 9CI

)

424

402
Name Index

508

Benzene

,

Benzene,

Benzene,

Benzene,

Benzene

,

Benzene

,

Benzene,

B enzene

,

Benzene

,

Benzene,

Benzene

Benzene

,

Benzene

Benzene

,

Benzene

Benzene

Benzene

Benzene

,

1-chloro~4-( 1-methylethenyl)- (9CI)

1-fluoro~4-( 1-methylethenyl)- (9CI)

1 -methoxy-4- C 1-methylethenyl)- (9CI)

1-methyl-4-( 1-methylethenyl)- (9CI)

1 , 1

' -etheny 1 i deneb i s- (9CI) 430

1

.2-

di fluoro- (9CI) 254

1.2-

dimethyl- (9CI) 367-368

1

.2.3.4-

tetrafluoro- (8CI9CI) 249 1.2.3.5-

tetrafluoro- (8CI9CI) 250

1 ,2, 4-tri fluoro- C8CI9CI) 251

1

.2.4.5-

tetrafluoro- C8CI9CI) 248

1 .

3-

d i fluoro- (9CI) 255-256

1.3-

dimethyl- (9CI) 373

1.3.5-

trifluoro- (8CI9CI) 252-253

1 , 3 , 5-tri methyl- (9CI)

1

.4-

(dimethyl-d3)- 359

1

.4-

di fluoro- (9CI) 257

1.4-

dimethyl- (9CI) 372

392

Benzenecarbonal 330

Benzenecarboxaldehyde 330

m-Benzenediamine 293

o-Benzenedi amine 29 1 p-Benzenedi amine 292

1 ,2-Benzenedi amine ( 9CI ) 29 1 1, 3-Ben zen ediamine ( 9CI

)

293

1,4-Benzenediamine ( 9CI 292

Benzenemethanam i ne ( 9CI

)

338

Benzenol 276

Benzofur D 292

Benzoic acid nitrile 329

Benzoic acid, methyl ester (8CI9CI)

Benzoic aldehyde 330

Benzol 269-270

Benzole 269-270

Benzonitrile (8CI9CI) 329

Benzoni tri le, p-formyl- 361

Benzonitrile, 4-formyl- C9CI)

Benzophenone C8CI) 426

Eenzoqu i nucl i d i ne 419

Benzoyl met hide 363

E enzoyl benzene 426

Benzylamine (8CI) 338

B i carburretted hydrogen 59

B i cycl o [ 2 . 2 . 1 ] hept-2-ene (9CI)

B i eye 1 o [ 2 . 2 . 1 ] heptene 350

Bicyclo[2. 2. 2]-1,4-diaza octane

B i eye lo [ 5 . 3 . 0 3 decapentaene 401

B i lor i n 23-25

Bi methyl 79-80

Bi s( .eta.-cyclopentadienyl)i ron

B i s( cyclopentadi enyl ) i ron 403

1,4-Bis(dimethylamino)butane 383

1,2-Bis(dimethylarnino)ethane 322

1,6-Bis(dimethylamino)hexane 418

1 , 3 — B i s(dimethylamino)propane

B i s( methyl~d3 ) ether 44

B i s( 1 -methylpropyl )ami ne 380

365

36 1

350

307-308

403

358

384

385

406

404
Name Index

509

N , N-B i s( 2-me-thy lpropyl )ami ne 378

Bi sL (dimethylami no)methyl]methane

Blausauere 19-20

Blood-coagulation factor IV 439

Blue Oil 278-280

Bon i ton 409

Borane, difluoro- (8CI9CI) 3 Borane, trifluoro- (9CI) 4 Borazine (8CI9CI) 7

. beta . -Borazi nyl radical 6 Borazole 7 Borazyne, cyclic trimer 7 Boron f luor i de 4 fluoride ( BF3 ) (8CI) 4 fluoride hydride (BHF2)

hydride ( B2H6 ) 5 hydride (B4H10) 9 tr i f luori de 4 69

12

(BrCN) 12

1212

358

Boron

Boron

Boron

Boron

Boron

Bromi c ether

B r om i ne cyan i da

Bromi ne cyan i de

Bromocyan

Bromocyan i de

Bromocyanide (BrCN)

Bromocyanoqen

Bromoethane 69

Bromomethane 25

Butafuma 200

Butal 172

12

12

Butaldehyde

n-3utan-1-ol

n-3utanal

Butanal (9CI)

Butanaldehyde

1 -Butanami ne 2-Butanami ne 2-Butanami ne,

1-Butanamine,

1-

Butanamine,

2-

Butan amine,

1-Butanamine,

172

191

172

(9CI)

( 9CI )

172

172

197

200

N-( 1-methylpropyl )- (9CI) 380

N-butyl- ( 9CI ) 379

N , N-di butyl- (9CI) 425

2-methyl- (9CI) 239

4,4, 4-tri f luoro- (9CI) 167

n-Butane 187

Butane . alpha delta . -oxi de 171

Butane (8CI9CI) 187

Butane, 1-cyano- 222

Butane, 1,4-epoxy- 171

1 .

4-

Butanedi ami ne (8CI9CI) 201

1 .

4-

Butanedi am i ne , N , N , N

' , N ' -tetramethyl- (8CI9CI)

Butanen i tr i le (9CI) 159

tert-Butanethi ol 193

n-Butanol 191

t-Butanol 192

tert-Butanol 192

Butanol 1 9 1

1-

Butanol (9CI) 191

Butanone 170

2-

Butanone (8CI9CI) 170

383
Name Index

510

2-Butanone,

2-Butanone

,

3-methyl- (8CI9CI)

3,3-dimethyl- (8CI9CI)

229

308

. alpha . -Butene 160

(E)-2-Butene 165

(Z)-2-Butene 163

ci s-Butene 163

c i s-2-Butene 1 6 3

i so-Butene 161-162

tran s-Butene 165

trans-2-Butene 165

2-trans-Butene 165

1-

Butene (SCI9CI)

Butene- 1 16 0

2-

Butene

,

2-Butene

,

1 - B u t e n e

,

1 -Butene

,

2-Butene,

160

(E>- (8CI9CI)

(Z)- (8CI9CI)

2-ethyl- 303

2-methyl- (8CI9CI)

2-methyl- (8CI9CI)

n-Butyl alcohol 191

tert-Butyl alcohol (SCI)

Butyl alcohol (SCI) 191

165

163

192

224-225

223

n-Butyl aldehyde

Butyl aldehyde

Butyl cyan i de

tert-Butyl ethyl

n-Butyl formate

Butyl formate

Butyl hydrox i de

tert-Butyl

tert-Butyl

172

172

222

ether 314

232

232

19 1 mercaptan 193

methyl ether 237

tert-Butyl methyl ketone

tert-Butyl sulfide (8CI)

Butyl tr i f 1 uo roacetate

1

Butyl ami ne 196

iso-Butylamine 196

n-Butylamine 197

t-Butylamine 195

2-

3utylamine 200

sec-Eutylami ne (SCI) 200

308

377

294

tert-Butylamine (SCI) 195

Butylami ne (SCI) 197

Butylamine, 4 >4 ,4-tri f luoro- (8CI)

n-Butylbenzene 412-413

t-Butylbenzene 410-411

tert-Butylbenzene 410-411

Butylbenzene 412-413

tert-Butyldi methylami ne 321

. alpha . -Butylene 160

. qamma . -Butyl ene 161-162

cis-Butylene 163

1-Butylene 160

Butyl ened i am i ne 201

1 , 4-Butylenedi ami ne 201

Butylen i mi ne 182

t-Butylmer captan 193

tert-Butylthi ol 193

N-Butyltrifluoroacetamide

167

298
Name Index -511 -

Butyral 172

i so-Butyraldehyde

n-Butyraldehyde

Butyraldehyde (SCI)

Butyric aldehyde

n-B u ty r on i t r i le

Butyron i tr i le (SCI)

Butyrylaldehyde

Butyrylon i tr i le

BAPN 111

BA5F U

r

50 1 D 292

BASF 238 184

BFV 21-22

C.I. Azoic Coupling

Developer 1 1 Developer 13

Natural White

169

172

172

172

159

159

172

159

Component

293

292

1 2 15

107 340

Oxidation

Oxidation

37 107

75 170

76 00 0 760 1 0 76 06 0

ethyl ester (8CI9CI)

Base 1 0 292

Base 16 291

340

215

278-280

29 1 C.I. 76060 292

Cadaverine 245

Calcium (8CI9CI) 439

Camp i lit 12 Carbacry 1 99

Carbamic acid, dimethyl-,

Carbinamine 36-37

Carb i no 1 32-34

Carbolic acid 276

Carbomethene 50

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon fluoride hvdride (CF2H2) 20

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon

Carbon

Carbonic acid gas 40-42

Carbonic acid, dimethyl ester (8CI9CI) 124

Carbonic acid, ethyl methyl ester (8CI9CI)

Carbonic anhydride 40-42

Carbonocyan i di c acid, ethyl ester (9CI) 154

Carbonothi o i c acid, S-ethyl 0-methyl ester (9CI)

Ca r boxyethane 119

bi sulf i de 42

bisulphide 42

chloride ( CC12

)

14-15

d i f 1 uo r i de 16 dioxide (3CI9CI) 40-42

disulfide (8CI9CI) 42

d i su 1 pit i de 42

fluoride ( CF2

)

16 fluoride ( CF4

)

17 fluoride hydride ( CF2H2

)

hydr i de nitride (CHN) 19

monoxide (8CI9CI) 39

oxide ( CO

)

39

oxide (C02) 40- 42

sulfide ( CS2

)

42

tetrafluoride (8CI) 17 trifluoride 18

c acid gas 40- 42

18 1

235

180
Name Index

512

Caustic potash 448

Caustic soda 449

Cesium hydroxide (8CI9CI)

Chelen 70

Chloracetic acid 51

Chloracetonitrile 47

Chlorene 70

Chi o r ethyl 70

Chi o r i dum 7 0 Chlorine cyanide 13

Chlorine cyanide (C1CN) 13

p-Chloro-. alp ha. -methylstyrene

4-Chloro - . alpha. -methyl styrene

4-Chloro- 1-ami nobenzene 27 1

1 -Chloro-2-cyanoethane 103

1-

Chloro-4-i soproprenylbenzene

6-Chloro-9H-purina 203

. a 1 pha . -Chi or oacet i c acid

Chioroacetic acid 51

.alpha.-Chloroacetonitrile

Chloroaceton i tr i le 47

2-

Chloroacetonitrile 47

m-Chloroaniline 272

p-Chloroaniline 271

3-

Chloroaniline 272

4-

Chloroaniline 271

p-Chi o r obenza 1 dehyde 325

4-Chlorobenzaldehyde 325

3-

Chlorobenzenami ne 272

4-

Chl orobenzenami ne 271

Chlorobenzene 264-265

Chlorocyan 13

Chi o r ocyan i de 13

Chlorocyanide (C1CN) 13

Chi o r ocyanoqsn 13

Chloroethane 70

Chi o r oethano i c acid 51

Chlorohydric acid 440

Chloromethane 26-27

Chioromethyl cyanide 47

2-(p-Chlorophenyl)propene

2-

(4-Chlorophenyl)propene

m-Chlorophenylami ne 272

p-Chlorophenylami ne 27 1

3-

Chl o r opr opanen i t r i 1 e 103

3-Chloropropanonitrile 103

. beta.-Chloropropi oni tri le

3-Ciiloropropionitrile 103

6-Chloropurine 203

. a 1 pha . -Chi o r o py r i d i ne 204

. qamma . -Chi o ropy r i d i ne 206

m-Chloro pyridine 205

o-Chloro pyridine 204

2-

Chl o r opy r i d i ne 204

3-

Ch loro pyridine 205

4-

Chl o r cpy r i d i ne 206

C in 1 o r y 1 7 0

44 1

384

384

384

5 1

47

384

384

103
Name Index

513

Chloryl Anesthetic 70

C i nnamene 362

Cloret

i

lo 70

Clorius 365

Coal naphtha 269-270

Co 1 1 o-Buegl att 23-25

Collo-Didax 23-25

Co 1 1 o-Gr i 1 1 re i n 449

Co 1 1 o-Tapetta 449

Combi-Schutz 131-132

Cratagine 366

Cumene (8CI) 388-389

Cumol 388-389

Curafume 25

1 -Cyano- 1 -methyl ethane 158

Cyanoaceton i tr i le 96

p-Cyanobenza ldehyde 361

4-Cyanobenzaldahyde 361

Cyanobenzene 329

Cyanobromi de 1

2

1 -Cyanobutane 222

Cyanocyclopropane 153

Cyanoethane 104

. beta . -Cyanoethylami ne 111

2-Cyanoethylami ne 111

Cyanoethylene 99

Cyanogen bromide (BrCN) 12

Cyanogen bromide (8CI9CI) 12

Cyanogen chloride (C1CN) 13

Cyanogen chloride (8CI9CI) 13

Cyanogen monobromide 12

Cyanomethane 56-57

N-(Cyanomethyl)dimethylamine 168

Cyanomethylami ne 62

1-Cyanopropane 159

2-Cya nopropane 158

. gamma . -Cyanopyr i di ne 26 1 2-Cyanopyr i d i ne 263

3-Cyanopyridine 262

4-Cyanopyri di ne 26 1 Cyanotrichloromethane 43

Cyclohexanami ne ( 9CI

)

310-31 1 Cyclohexanone (8CI9CI) 299

Cyclohexatriene 269-270

Cyclohexene, 1-methyl- (8CI9CI) 352

Cyclohexylami ne C8CI) 310-311

Cycl ooxabutane 117

Cycl opentacycl oheptene 401

Cyclopentane, methylene- (8CI9CI)

Cyclopentene , 1-methyl- (8CI9CI) 295

Cyclopentene, 1,2-dimethyl- (8CI9CI)

Cyc 1 open t i m i ne 233-234

9-Cyclopentyladen i ne 408

Cyclopropane (8CI9CI) 106

Cyclopropane, (

1 -methyl etheny 1) - (9CI)

Cyclopropane, ethenyl- (9CI) 218

Cyclopropane, methyl- (8CI9CI) 164

296

353

297
Name Index

514

Cyclopropane, vinyl- (8CI) 218

Cyc 1 opr opaneca rbon i -fc r i 1 e (8CI9CI) 153

Cyclopropanecarboxyl i c acid, methyl ester (8CI9CI)

Cycl opr opanen i t r i 1 e 153

Cyclopropene (8CI9CI) 102

Cyclopropyl cyanide 153

Cyclopropyl methyl ketone 219

2-Cyclopropyl- 1 -propene 297

Cyclopropylethylene 218

Cyclopropyln i tr i le 153

2-Cycl opropyl propene 297

Cyclotetramethylene oxide 171

Cyd 396

Cymon ic acid 54

Cy pent i 1 233-234

Cyt 155

Cytidine (9CI) 396

Cytosine (8CI) 155

Cytosine riboside 396

Cytosinimine 155

p-CA 271

CCS 203

CP 28

CP 32

D 3 3 L V Dabco

Dabco 33LV

19 1 246

212-213

307-308

307-308

307-308

Decahydrotetraborane

Decanami ne 417

1-Decanamine (9CI)

n-Decylamine 417

1-Decylamine 417

Decylamine (3CI) 417

Dehydro-p-cymene 404

Demsodrox 87

Denatured ethanol

Deoxythym i d i ne 414

2’-Deoxythymi di ne Deuterium (8CI9CI)

Deuterium oxide 442

Deuterium oxide (D20)

Developer C 293

Developer H 293

Developer M 293

Developer PF 292

Devoton 120-121

Dew Pearl 215

9

4 17

82-83

4 T4

441-442

442

Di - . pi . -cyclopentad i enyl iron

Di -n-butylami ne 379

Di-n-propyl ether 313

Di -n-propylami ne 320

Di -sec-butylami ne (8CI) 380

Di -t-Butylami ne 332

D

i - tert-butyl sulfide 377

Di-tert-butylamine (8CI) 382

2,6-Di-tert-butylpyridine

D

i -2~pr openy lam i ne 300

429

403

221
Name Index

5 15

4 0 3 D

i -2-propynylami ne (8CI) 284

Di-2,4~cyclopentadien-1-yli ron

Di acety Imethane 220

Diallyl ether 300

Diallylamine (SCI) 300

1 > 6 — D i ami no-n-hexane 323

m-Di ami nobenzene 293

o-D i am i nobenzene 291

p-D i am i nobenzene 292

1 , 2~D i am i nobenzene 291

1 , 3-D i ami nobenzene 293

1 .

4-

D i am i nobenzene 292

1.4-

Di a mi nobutane 201

1 , 2~D i am i noethane 94

1 , 6~Di ami nohexane 323

1.5-

Diaminopantane 245

1 . 3 — D i ami nopropane 143

1 , 2~D i azabenzene 145

1 .

3-

Di azabenzene 146

1 . 4 — D i azabenzene 147

1

.4-

Diazabicyclo[2.2.2loctane (8CI9CI)

1 .

4-

Di azacyclohexane 188

Diazene, dimethyl-, (E)~ (9CI) 8 1 m - D i a z i ri e 146

p-Di azi ne 147

1 , 2~D i az i ne 145

1 , 3-D i az i ne 146

1 , 4-D i az i ne 147

Di azi r i ne 2 1 D i azomethane 2 1 borana 5 borane (B2H6) 5 borane( 6 ) (8CI9CI)

boron hexahydride

butylamine (8CI)

chlorocarbene

chloromethylene

DD

DD

DD

DD

DD

DD

DDD

DN,N-Di ethylami ne Diethylamine (8CI)

D i ethyl am i ne , N-methylD i ethylami ne, 1-methylM, N-Di ethylami nobenzene

Di ethylan i 1 i ne 415

N

,

N-D i ethylan i line

Diethylene dioxide

1 , 4~Di ethylene dioxide

Diet hy lane ether 175

Diethylene imidoxide

5

5379

14-15

14-15

cyanomethane 96

cyclopentadi enyl i ron 403

deuterium oxide 442

etary calcium 439

187

ether 189-190

ketone 225

oxide 189-190

sulfide 194

ethyl

ethyl

ethyl

ethyl

ethyl

198

198

( 8CI

)

(8CI

4 15

240

243

4 15

175

184

175

307-308
Name Index

- 516

Diethylene oxide 175

Diefchylene oximide 184

D i ethyl ened i ami ne 188

Di ethyl ene i mi ne 188

D i ethy 1 an i mi de oxide 134

D i e t hy lmethy 1 am i ne 240

,N-Diethylmethylamine 240

Di ethylphenylami ne 415

Di ethylpropylami ne 356

D i et hy 1 th i oether 194

m-Di fluorobenzene 255-256

o~Di f luorobcnzene 254

p-Di fluorobenzene 257

1 , 2~Di fluorobenzene 254

1 .

3-

Di fluorobenzene 255-256

1 , 4~Di fluorobenzene 257

Difluoroborane 3 Di fluorocarbene 16

2 .

2-

Di f luoroethanol 60

c

i

5 - 1 , 2-D i f 1 uo r oethene 49

trans- 1 , 2-Di f luoroethene 49

1 ,

1 -D i fl uo roe then e 48

2 .

2-

Di f luoroethylami ne 72

C E

) - 1 , 2 -D i f 1 uo r oet hy 1 ene 49

ci s-Di f luoroathylene 49

c i s- 1 > 2~D i f luo r oethy 1 ene 49

trans-Di f luoroethylene 49

trans-l,2-Difluoroethylene

1 ,

1 -D i fl uo r oethy 1 ene 43

Di f luoromethane 20

Difluoromethylene 16

Di f luoromethylene radical

Di f lurocarbene 16 3/4-Dihydro~2H-1 ,4-ethanoqui

1 ,6-Dihydro-6-iminopurine

3,6-Dihydro-6-iminopurine

Dihydrogen monosulfida

Dihydrogan selenide 457

Di hydrogen sulfide 454-

D i hydroox i r ene 65

Di hydrouridine 397

5 , 6 — D i hydrour i di ne 397

2 .

4-

Di hydroxy-5-methylpyr i mi

2.4-

Di hydro xypyrimi di ne

D i i sobuty lam i ne (SCI)

Di isopropyl ether 312

Diisopropyl oxide 312

Diisopropyl sulfide 316

Di i sopropylami ne (SCI) 317

Di i sopropylethylami ne 381

N , N-D i i sopropy 1 ethylam i ne 381

Dilute hydrochloric acid 440

49

16 noline

214

214

454-456

456

dine

149

378

216

Di mazi

n

D i maz i ne Dimethyl

D i methyl

D i methyl

93

93

79-80

carbonate

ether

124

84-86

419
Name Index

- 517 -

Dimethyl ketone 112-114

Dimethyl monosulfide 89

Dimethyl oxide 84-86

Dimethyl sulfide 89

Dimethyl sulfoxide 87

Dimethyl sulphoxide 87

Dimethyl thioether 89

N » N-Di methyl-m-methy lan i 1 i ne 394

Di methyl-m-tolu i di ne 394

N , N-Di methyl -m~to 1 u i di ne 394

Di methyl-tert-butylami ne 321

N, N-Di met hyl-tert-butylamine 321

N,N-Dimethyl-N-(3-aminopropyl)amine

1 .

2-

Dimethyl - 1 -cycl opentene 353

N,N-Dimethyl-1,3-diami nopropane 244

N,N-Dimethyl-1,3-propanediamine 244

N,N-Dimethy 1-1,3-pro pylenediamine

3 .

3-

Di methyl-2-butanone 308

2 , 2~Di methyl -3-butanone 308

N, N-Di met hyl-3-methylani line 394

2.

4-

Di methyl-3-thi apentane 316

N , N-D i methyl -4-am i nopyr i d i ne 351

N , N-Di methyl-4-pyr i di nami ne 351

Di methylacetami de 185

N , N-Di methylacetami de 185

Di methylacetone 225

D i methy lam i de acetate 185

D i methy lam i ne (8CI) 91-92

4-D i methylam i nepy r i d i ne 351

3-(Dimethylamino)-1-propanamine 244

3-(Dimethylamino)-1-propylamine 244

( D i methy 1 am i no ) a cet on i t r i 1 e 168

( Di methylami no ) benzene 375-376

C(Dimethylamino)methyl]trimethylsilane

3-

(Dimethylamino)propylamine 244

. gamma. -(Dimethylamino)pyridine 351

4-

( D i methylam i no ) pyr i d i ne 351

1-Dimat hylamino-3-aminopropane 244

2~Di methylami nopropane 241

. gamma .-Di methylami nopropylamine 244

Di methylan i 1 i ne 375-376

244

244

N,N-Dimethylani line

m-Dimethylbenzene

o-Dimethylbenzene

p-Dimethylbenzena

1

.2-

Dimethylbenzone

1 .

3-

Di met hylbenzene

1 .

4-

D i methyl benzene 372

2 , 2 — D i methylbutanone 308

3,3-Dimethylbutanone 303

Di methylcarbi nol 131-132

1,2-Dimethylcyclopentene

( E)-Di methyldi azene 81

Di methylene oxide 65

Di methylenedi ami ne 94

Di methylenemethane 101

Di methy len i mi ne 74-75

375- 376

373

367-368

372

367-368

373

353

324
Name Index

518

1 , 1 — D l methylethanethi ol 193

1 ,

1 -Di methylethanol 192

Di methylethoxyformami de 235

N , N~D i methy 1 ethylami ne 199

1 .

1

D i methyl ethy lam i ne 195

Di methylethylbenzene 410-411

c i s- 1 , 2~D i methyl ethyl ene 163

trans- 1 , 2 — D i methylethylene 165

1 .

1

D i methyl ethy 1 ene 161-162

D i methy 1 f o rma 1 dehy de 112-114

Di methylformami de 129

N , N-Di methylf ormami de 129

u-D i methylhydra^i ne 93

unsym-Di methylhydrazi ne 93

N , N-Di methylhydrazi ne 93

1 ,

1 -D i methylhydrazi ne 93

Di methyl i s*o propylamine 241

N,N-Dimethyl isopropylamine 241

Di methylmethane 130-131

N , N-Di methylneopentylami ne 357

Di methylphenylami ne 375-376

Di methy 1 pho sph i ne 92

.alpha. , . alpha. -Dimethylpropylamine 239

1.1-

Dimethylpropylamine 239

2.2-

Dimethylpropylamine 242

N , N~Di met hylpropylenedi amine 244

.alpha., .alpha. '-Dim ethyl pyridine 344

.alpha. , .garrma.-Dimethylpyridine 343

2, 4-Dimethyl pyridine 343

2 , 5~D i methy 1 py r i d i ne 345

2 , 6 -D i methyl py r i d i ne 344

3 , 5 — D i methylpyr i di ne 346

. alpha ., p~Di methy 1 styrene 404

. alpha ., 4 — D i methyl styrene 404

p , . a 1 pha . -D i met hy 1 sty r ene 404

1 ,

1 ' -Di methyltr i ethylami ne 381

N,N-Dimethyltrimethylenediamine 244

DimethylC2-(dimethylamino)ethyl] amine

D i mex i de 87

D i n i t r ogen monox i de 47 1 D i n i t r ogen oxi de 47 1

1 ,4-Di oxacycl ohexane 175

p-Di oxan 175

D i oxan 175

1 , 4 - D i o x a n 175

D i oxane 175

p-Dioxane C8CI) 175

1.4-

Dioxane (9CI) 175

1.4-

Dioxin, tetrahydro- 175

2 .

4-

D i oxopentane 220

2. 4

Dioxo pyrimidine 149

Di oxyethylene ether 175

Diphenyl ketone 426

D i phenyl ( ethyl ) pho sph i ne oxide 431

D i pheny lam i ne (8CI) 421

N , N- D i pheny lan i 1 i ne 437

1 ,

1 -D i phenyl ethene 430

322
Name Index

519

. alpha . , . alpha. -Diphenylethylene

unsym. -Di phenylethylene 430

Diphenylethylene 430

1 , 1 — D i phenylethylene 430

D i pheny lmethanone 426

Di phenylmethylphosphi ne oxide

Di pi rartr i 1-tropi co 87

Diplogen 441-442

Diproparqyl ether

Dipropargyl oxide

Di propargylami ne 284

Dipropyl ether 313

Dipropyl oxide 313

Dipropyl sulfide 315

Dipropyl thioether

n~Di propylami ne 320

Di propylami ne (8CI)

Direct Brown BR 293

Di rect Brown GG 293

Di spermi ne 188

Distilled water 451-453

Di thi ocarbon i c anhydride 42

430

427

277

277

315

320

Divinylene oxide

Di vi nyleni mi ne Dol i cur 87

Dromi sol 87

Dry ice 40-42

Dublofix 70

Durafur Black R

150

152

292

Durasorb 87

DDNU 430

DEK 225

DFA 421

DMA 185

DMF 129

DMF (amide)

DMFA 129

DMS 89

DMS 7 0 87

DMS 90 87

DMSO 87

DPA 421

DT 4 14

DThyd 4 14

Elayl 59

El egas 446

Embaf ume 25

129

3,6- Endom ethyl enecycl o hexene

Epoxyethane 65

1.2-

Epoxyethane 65

1.3-

Epoxypropane 117

Eraverm 188

Essence of Mirbane 268

Essence of Myrbane 268

ps-Estragole 406

Ethanal 63~65

Ethanamide 75

350
Name Index

520

Ethanamine (9CI) 90

Ethanam i ne

,

Ethanami ne,

Ethanami ne

,

Ethanami ne,

Ethanamine,

E-thanami ne

,

Ethanam i ne Ethanam i ne Ethanam i ne Ethanami ne Ethanam i ne

,

Ethanamine,

Ethanami ne. Ethane (8CI9CI) 79-80

Ethane C d i th i o i c ) ac i d , methyl ester 125

Ethane

,

Cmethylthi o

) - (9CI)

Ethane

,

bromo- (SCI9CI) 69

Ethane chloro- (8CI9CI) 70

Ethane, fluoro- (8CI9CI) 7 1 Ethane

,

iodo- (8CI9CI) 73

Ethane

,

methoxy- C 9CI

)

133

Ethane

,

nitro- (8CI9CI) 77

Ethane, 1,1 f -oxybis- (9CI) 189-190

Ethane, 1 , 1

* -thi obi s- C9CI) 194

Ethane, 2-ethoxy- 1 , 1 , 1-tri fluoro- (9CI) 157

Ethanecarboxyl i c acid 119

1 .

2-

Ethanedi ami ne (9CI) 94

1 .

2-

Ethanedi ami ne, N , N , N

' , N ’ -tetramethyl- (9CI) 322

Ethanen i t r i 1 e 56-57

Ethanethioic acid, S-methyl ester (9CI) 118

Ethanethiol (8CI9CI) 88

Ethanoic acid 66-67

Ethanol (9CI) 82-83

Ethanol, 2 , 2-di fluoro- (8CI9CI) 60

Ethanol, 2,2,2-tri chloro- (8CI9CI) 52

Ethanol, 2 , 2 , 2- t r i f 1 uo r o- (8CI9CI) 55

Ethanol, 2 , 2 , 2- t r i f 1 uo r o~ , formate (9CI) 98

Ethanone, 1 - ( 3-py r i d i ny 1

) - (9CI) 331

Ethanone, 1 - ( 4-pyr i d i ny 1

) - (9CI) 332

Ethanone, 1 -cycl opropy 1 - (9CI) 219

Ethanone, 1-phenyl- (9CI) 363

2H- 1 , 4-Ethanoqui nol i ne, 3,4-dihydro- C8CI9CI) 419

Ethene (9CI) 59

Ethene oxide 65

Ethene, cyclopropyl- 218

Ethene, fluoro- C9CI) 53

Ethene, trifluoro- (9CI) 45

Ethene, 1 , 1-di fluoro- (9CI) 48

Ethene, 1 , 2-di fluoro- , (E)- (9CI) 49

Ethene, 1 , 2-di fluoro- , (Z)- (9CI) 49

Ethanone (9CI) 50

Ether 189-190

Ether chloratus 70

Ether cyanatus 104

Ether hydrochloric 70

Ether muriatic

N-ethyl- (9CI) 198

N-ethyl-N-methyl- (9CI) 240

N-ethy 1 -N-pr opy 1 - 356

N-ethyl i dene- (9CI) 133

N-methyl- (9CI) 140-141

N , N~d i ethyl- (9CI) 319

N , N-di methyl- (9CI) 199

2-fluoro- (9CI) 80

2-methoxy- (9CI) 141

2, 2-di fluoro- (9CI) 72

2.2.2-

tri fluoro- (9CI) 61-62

2.2.2-

trifluoro-N-methyl- (9CI) 110

2 , 2 , 2~tr i f luoro-N , N-di methyl- (9CI) 166

70
Name Index

52 t

189-190

7 1 122-123

82-83

79-80

88

82-83

236

Ether, ethyl isopropyl (8CI) 236

Ether, ethyl methyl (SCI) 133

Ether, ethyl 2 , 2 , 2-tr i f luoroethyl (8CI)

Ether, tert-butyl ethyl (8CI) 314

Ether, tert-butyl methyl (8CI) 237

Ethirydine 74-75

Ethoxyethane 189-190

Ethyl acetate 176-177

Ethyl acetic ester 176-177

Ethyl alcohol (8CI) 82-83

Ethyl aldehyde 63-65

Ethyl bromide 69

Ethyl carbinol 132-133

Ethyl chloride 70

Ethyl cyanide 104

Ethyl cyanoformate 154

Ethyl di methylcarbamate 235

Ethyl ethanoate 176-177

Ethyl ether (8CI)

Ethyl fluoride

Ethyl formate

Ethyl hydrate

Ethyl hydride

Ethyl hydrosulfide

Ethyl hydroxide

Ethyl iodide 73

Ethyl i sopropyl ether

Ethyl ketone 225

Ethyl mercaptan 88

Ethyl methanoate 122-123

Ethyl methyl carbonate 181

Ethyl methyl ether 133

Ethyl methyl ketone 170

Ethyl methyl sulfide 135

Ethyl monosulfide 194

Ethyl ni trate 78

Ethyl nitrile 56-57

Ethyl sulfhydrate 88

Ethyl sulfide (8CI) 194

Ethyl tert-butyl ether

Ethyl tert-butyl oxide

Ethyl thioalcohol 88

Ethyl thioether 194

Ethyl trifluoroacetate

Ethyl N , N~d i methyl ca rbamate 235

S-Ethyl 0-methyl thi ocarbonate 180

N-Ethyl-N-methylan i 1 i ne 395

N-Ethyl-N-phenylami ne 374

N- Ethyl -N , N~d i i sopropy lam i ne 381

Ethylamine (8CI) 90

Ethylamine, N-ethy 1 i dene- (8CI) 183

Ethylamine, N-methyl- (8CI) 140-141

Ethylamine, N , N-di methyl- (8CI) 199

Ethylamine, N,N, 1-trimethyl- (SCI)

Ethylamine, N , N , 1

, 1-tetramethyl- (8CI)

Ethylamine, 2-fluoro- (8CI) 80

Ethylamine, 2-methoxy- (8CI) 141

314

314

151

157

24 1 321
Name Index

522

Ethylamine, 2 , 2~di fluoro- (8CI) 72

Ethylamine, 2 , 2 , 2-tr i f luoro- (8CI) 61-62

Ethylamine, 2 > 2 , 2~tri f 1 uo r o-N-methy 1 - C8CI)

Ethylamine, 2 , 2 , 2~t r i f 1 uo ro~N , N~d i methy 1- (8CI)

N-Ethylami nobenzene 374

Ethylan i line 37 4 N-Ethylani li ne 374

N-Ethyibenzenami ne 374

Ethylbenzene 369-371

Ethyl benzol 369-37 1 Ethyldi i sopropylami ne 381

N-Ethyldi i sopropylami ne 381

Ethyldi phenylphosphi ne oxide

Ethylene (8CI) 59

oxide (8CI ) 65

tri f luor i de 45

cyclopropyl- 218

fluoro- (SCI) 53

trifluoro- (8CI)

1 .

1-

di fluoro- (8CI)

1 , 1-di phenyl1 , 2~di fluoro-,

1 .

2-

di fluoro-,

1,2-Ethylenedi amine

Ethylenedi ami ne (8CI)

Ethylenedi ami ne, Nj

Ethyleneimine

Ethylene

Ethylene

Ethylene,

Ethylene,

Ethylene,

Ethylene,

Ethylene,

Ethylene,

Ethylene,

431

45

48

430

( 8CI

)

(8CI

( 8CI

)

(E)-

(Z)-

94

94

N,N' ,N f -tetramethyl74-75

49

49

( 8CI ) N,N’-endo-Ethylenepiperazine 307-308

1 .

4-

Ethylenepi perazi ne 307-308

1 .

4-

Ethylenepi per i di ne 354-355

Ethyl en i m i ne (SCI) 74-75

Ethyl ethylene 160

Ethylformic acid 119

Ethylic acid 66-67

Ethyl i deneethylami ne 183

N-Ethy 1 i deneethylami ne 183

Ethyl i sopropylami ne 243

N-Ethyl i sopropylami ne 243

Ethylmethylami ne Ethylphenylamine

Ethylthioethane

Exhaust gas 39

E5 369-371

El 74-75

ETO 65

Fannoform 21-22

Fast Orange GC Base

Ferrocene (8CI9CI)

Ferrotsen 403

Flue gas 39

Fluorhydric acid 443

p-Fluoro-. alpha. -methylstyrene 385

4-Fluoro-. alp ha. -methylstyrene 385

1-Fluoro-4-isopropenylbenzene 385

Fluoroacetic acid 54

m-Fluoroan i 1 i ne 274

p-Fluoroan i 1 i ne 273

140-141

374

194

272

403

1 10 166

322
Name Index

3- 523

FI uoroan i 1 i ne 274

4-

F 1 uoroan i 1 i ne 273

m~Fluorobenzaldehyde 327

p- FI uo robenza 1 dehyde 328

3-

Fluorobenzaldehyde 327

4-

Fluoroberizaldehyde 323

Fluorobenzene 266-267

Fluoroethane 7

1

Fluoroethanoic acid 54

Fluoroethene 53

. beta . -Fluoroethylami ne 80

2-Fluo.roethylami ne 80

Fluoroethylene 53

Fluoroform 18 Fluoromethane 27

2-

( 4-Fluoropheny 1 ) propene 385

p-Fluorophenylami ne 273

p- FI uoro pyridine 209

2~ FI uo ropy r i d i n e 208

3-

FI uoro pyridine 207

4-

Fluoropyri di ne 209

Fluoryl 18

Formal dehyde (8CI9CI) 21-22

Formaldehyde solution 21-22

Formaldehyde, qas 21-22

Formal i n 2 1-22

Formal i th 2 1-22

Formamide, N~methyl- (8CI9CI) 76

Formamide, N , N-di methyl- (8CI9CI)

Formic acid (8CI9CI) 23-25

acid, butyl ester (8CI9CI)

cyano-, ethyl ester (8 Cl)

ethyl ester C8CI9CI)

isopropyl ester (8CI)

methyl ester C8CI9CI)

propyl ester (8CI9CI)

1 -methyl ethyl ester (9CI)

aldehyde 2 1-22

anammonide 19-20

23-25

21-22

acid,

acid,

acid,

acid,

acid,

acid,

F o r rn i c Formic

Formic

Formic

Fo rm i

c

Formic

Formic

F o r m i c Formic

Formi soton

Formol

Formonitrile 19-20

p-Formylani sole 366

p- Fo rmy 1 benzon i t r i 1 e 361

4-Formylbenzoni tri le 361

N-Formyldi methyl ami ne Formylic acid 23-25

p-Formyltoluene 364

129

Fouram i ne D 292

Fourrine D 292

Fourr i ne 1 292

Freon F-23 18

Freon 14 17 Freon 23 18

Freon 290 130-131

Freon 32 20

Freon 40 26- 27

129

232

154

122-123

179

67-69

173-174

179
Name Index

524

Freon 41 27

Freon 600 187

Fuers Rohr 449

Fumiqrain 99

Fur Black 41867 292

Fur Brown 41866 292

Fur Yellow 292

Furan (SCI9CI) 150

Furan, tetra hydro- C8CI9CI)

Furan, te-trahydro-2-methyl17 1 (8CI9CI) 226

acid

54

66-67

62

62

N-methy 1-

2 15

1 1 1

( 9CI

)

428

Furanidine 171

Furfuran 150

Furro D 292

Futramine D 292

Fyde 21-22

FC 14 17 T-Gas 65

Genetron 1132a 48

Genelron 23 18

Gcncrron 32 20

Gi fblaar po i son Glacial acet i

c

Glyci neni -fcri le

Glycincnitrile

Glyc i non i t r i le

,

Guan i n 215

Guanine (8CI)

Guanine enol 215

Guanine, 8-methyl- (8CI) 290

Guanosi ne, 2' ,3'-0-( 1-methylethylidene)-

Guanosine, 2 ’ ,

3

1 -0- i sopr opyl i dene- (SCI)

Hal on 1001 25

Haltox 25

Hartosol 131-132

Heavy water 442

Heavy water~d2 442

0-

Helium 465-466

p-Helium 465-466

Helium (8CI9CI) 465-466

Helium-4 465-466

Hemostyp 1 9

1

1-

Hcptanamine (9CI) 355

n-Heptylami ne 355

Heptylamine (SCI) 355

Hexaf luorobenzene 246

Hexahydro-s-tr i azabori ne 7 Hexahydroan i 1 i ne 310-311

Hexahydropyrazi ne 188

Hexa hydro pyr i di ne 233-234

Hexamethyl benzene 423

Hexaine-thylenebis(dimethylamine) 4 18

Hexamethy lenedi ami ne 323

1-Hexanamine (9CI) 318

1 , 6 -Hexaned i am i ne (8CI9CI) 323

1 , 6-Hexanedi ami ne, N , N , N

" , N ’ -tetramethyl- (8CI9CI)

Hexanon 299

Hexazane 233-234

428

4 18
Name Index

525

n-Hexylamine 318

1-Hexylamine 318

Hexylamine (8CI)

1 , 6-Hexylenedi amine

318

323

Hyadur

Hydrazi ne Hydrazi ne,

Hydr i odi

c

Hydr i odi

Hydrobromi

c

Hydrobromi

c

87

(8CI9CI)

1 , 1 — d i methyl

acid (8CI9CI)

ether 73

acid (8CI9CI)

ether 69

<+64 (8CI9CI)

447

93

Hydrochloric acid (8CI9CI)

Hydrochloric acid gas

Hydrochloric ether 70

Hydrochloride 440

Hydrocyanic acid (8CI9CI)

440

Hydrocyanic ether

Hydrofluoric acid

Hydrofluoric acid

Hydrogen (8CI9CI)

104

(3CI9CI

)

gas

1 1 440

19-20

443

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen

Hydrogen-2

Hydrosulfur i

c

ac l

arsen i de

bromide 11 bromide (HBr)

carboxyl i

c

chloride

chlor i de

cyan i de

f 1 uo r i de

fluoride

iodide

iodide ( HI

)

phosphi de

seleni de

443

449-45

1

2

1 1 d 23-25

440

CHC1) 440

19-20

443

(HF) 443

447

447

462-464

457

seleni de (H2Se) (8CI9CI)

sulfide 454-456

sulfide ( H2S ) (8CI9CI)

sulphide 454-456

441-442

acid 454-456

457

454-456

Hydrouracil, 1- . beta . -D-r i bofuranosyl- (8CI)

6 -Hydr oxy- 1 H-pu r i ne 211

Hydroxybenzene 276

( Hydroxymethyl )trichloromethane 52

6-Hydroxypur i ne 211

2-Hydroxypyr i mi di ne 148

Hypnon 363

Hypnone 363

Hypoxanthine (8CI) 211

Hypoxanthine enol 211

Hypoxanthine, 2-amino- 215

Hytrol 0 299

HFA 54

HMDA 323

Ice 451-453

Imidazole, 1-methyl- (8CI) 156

IH-Imidazole, 1-methyl- (9CI) 156

Imidole 152

397
Name Index

526

I m s o 1 A Inf i Itr i na

I odo ethane

Iodomethane

13 1 •132

87

73

28

Iron

Iron

Iron

Iren

Iron

I r on

b i 5 ( cycl open tad i en i de ) 403

carbonyl (Fe(C0)5) (SCI) 202

carbonyl (Fe(C0)5), (TB-5-11)- (9CI)

di cyclopentadi enyl 403

pent a carbonyl

bi s( . eta . 5-2

Iscobrcma 25

. beta . -I soamylene

. qnmma . ~ I soamylene

1-

Isoamylene 224-225

I sobutana 1 169

2-

Isobutanethiol 193

Isobutene 161-162

I so butyl ami ne (SCI)

Isobutylene 161-162

I Sobu tyr a 1 dehyde (SCI)

I sobuty rami de (SCI)

Isobutyric acid> methyl

Isobutyrimidic acid

Isobutyronitrile (8CI)

Isocumene 390-391

Isohol 131-132

Isonicotinic acid nitrile

Isonicotinonitrile (8CI)

I sopr opaneth i o 1 134

Isopropanol 131-132

p-I soproponylan i sole

Isopropenylbenzene

I sopr openy 1 cycl opr opane

p-Isoproponyltoluene

4-Isopropenyltoluene

2-Isopropoxypropane

Isopropyl alcohol (SCI)

Isopropyl aldehyde

Isopropyl cyanide

Isopropyl ether (SCI)

Isopropyl formate

Isopropyl mercaptan

Isopropyl methyl ketone

Isopropyl nitrile

Isopropyl sulfide (SCI)

Isopropylamine (SCI)

I sc pr opy 1 am i ne , N-ethyl202

cyclopen tadien-1-yl) -

223

224-225

196

169

186

ester (8CI) 231

1S6

26 1

406

387

404

4 04

3 12

169

158

179

134

158

137

158

26 1

297

131-132

3 12

229

3 16 243

Isopropylbenzene 388-389

Isopropyldi methylami ne 241

Iscprcpyldi phenyl pho sph i ne oxi de

I sopropyl forma Idehyde 169

I sopropylf ormami de 186

I sopropyl i dene quanosine 428

2 * , 3

' -Isopropyl i denequanosi ne

2* ,3’-0-Isopropylidenequanosine

Isopropylidenemethylene 161-162

2'»3 , -Isopropylideneuridine 422

432

423

423

202

403
Name Index

527

2

, ,3 , -0-Isopropylideneuridine 422

I sopropylthi ol 134

Isopurine, ribosyl- 405

I sothi ocyanatomethane 58

I sothi ocyan i c acid, methyl ester (8CI)

p-Isoxazine, tetrahydro- 134

Ivalon 21-22

Izal 276

Jaysol 82-83

Jaysol S 82-83

Kelene 70

Ketene (8CI) 50

Ketone, cyclopropyl methyl (8CI) 219

Ketone, methyl 3-pyridyl (8CI) 331

Ketone, methyl 4-pyridyl (8CI) 332

. beta . -Ketopr ooane 112-114

Krypton (8CI9CI) 466-467

Lauqhi ng gas 471

L euco-4 2 14 Levoxine 464

Liquefied petroleum gas 130-131

Liquefied petroleum gas 187

Lithium hydroxide (8CI9CI) 448

Lithium Hydrate 448

Lumbr i cal 188

Luprosi 1 119

. alpha alpha -Luti di ne 344

2.4-

Lutidine (8CI) 343

2.5-

Lutidine (SCI) 345

2.6-

Lutidine (SCI) 344

3,5-Lutidine (SCI) 346

Lutosol 131-132

Lysoform 21-22

LPG 130-131

LPG 187

Magnesium (8CI9CI) 467

Magnesium molecule 468

Malonic acid dinitrile 96

Malonodi n i tr i le 96

Malononitri le (8CI) 96

Manxin 416

Manx i ne 416

Mar sh gas 30-31

Mear lma id 215

Mel 1 i tene 423

Mercaptoethane 88

Mercaptomethane 34-35

2-Mercaptopropane 134

Mesi tylene (SCI) 392

Metacetone 225

Metacetonic acid 119

Metadiazine 146

Methacetone 225

Methacide 333-336

Methan-d3-ami ne, N , N-d i ( methyl -d3 ) - (9CI)

Methana 1 21-22

Methanamine (9CI) 36-37
Name Index

528 -

Methanami ne,

Methanami ne,

Methanami ne,

Mathanam i ne

,

Methanami ne

,

N-ethyl-N-methyl- 199

N-methyl- (9CI) 91-92

N , N-di methyl- (9CI) 138-139'

N,N-dimethyl-1-(tri methyl si ly 1 ) - 1,1, 1-tri f luoro-N , N-di methylMethane (8CI9CI) 30-31

Methane~d3, oxybis- (9CI) 44

Methane, bromo- C8CI9CI) 25

chloro- (8CI9CI) 26-27

cyano- 56-57

diazo- (8CI9CI) 21

di cyano- 96

difluoro- (8CI9CI) 20

ethoxy- 133

fluoro- (8CI9CI) 27

iodo- C8CI9CI) 28

i sothi ocyanato- C9CI) 58

nitro- C8CI9CI) 29

oxybis- (9CI) 84-86

( 9CI

)

109

Methane,

Methane

,

Methane

Methane

Methane,

Methane

,

Methane

Methane

Methane

,

Methane,

Methane

Methane,

Methane

Methane,

Methane,

87

17

18

237

sulfinylbis- C9CI)

tetrafluoro- (9CI)

thiobis- ( 9CI ) 89

trifluoro- (8CI9CI)

Methanecarbon i tr i le 56-57

Methanecarboxami de 75

Methanecarboxyl i c acid 66~67

Methanethiol (8CI9CI) 34-35

Mathanoic acid 23-25

Methanol (8CI9CI) 32-34

Methanone, diphenyl- (9CI) 426

p-M ethoxy- .alpha. -methylstyrene

4-M ethoxy-. alpha. -methyl styrene

2-Methoxy- 1 -am i nobenzene 347

1

Methoxy-2-ami noethane 141

2-

Methoxy-2-methylpropane

m-Methoxyan i 1 i ne 349

o-Methoxyan i 1 i ne 347

p-Methoxyan i 1 i ne 348

2-

Methoxyan i 1 i ne 347

3-

Methoxyan i 1 i ne 349

4-

Methoxyan i 1 i ne 348

p-Methoxybenzaldehyde

4-Methoxybenzaldehyde

4-Methoxybenzenam i ne 348

Methoxybenzene 337

4-Methoxybenzeneami ne 2-Methoxyethanami ne 141

.beta. -Met hoxyethylamine

Methoxyethylami ne 141

2-Methoxyethy lam i ne 141

Methoxymethane 84-86

2-(p~Methoxyphenyl)propene

2- (p-Methoxyphenyl) propylene

p-Methoxypheny lam i ne 348

. beta . -Methoxypy r i di ne 289

. gamma . -Methoxypyr i d i ne 285

2-Methoxypyr i di ne 287-288

406

406

366

366

348

141

406

406

324
Name Index

3- 529

Methoxypyr i d i ne 289

4-

Methoxypyr i di ne 285

Methyl . beta . -pyr i dy 1 ketone 331

Methyl acetate 120-121

Methyl alcohol 32-34

Methyl aldehyde 21-22

Methyl benzenecarboxylate 365

Methyl benzoate 365

Methyl bromide 25

Methyl carbonate 124

Methyl carbonate ((Me0)2C0) 124

Methyl chlor i de 26-27

Methyl cyanide 56-57

Methyl cyclopropanecarboxylate 221

Methyl cyclopropyl ketone 219

Methyl cyclopropylcarboxylate 221

Methyl ether (SCI) 84-86

(Methyl ether)-d6 (8CI) 44

Methyl ethyl ether 133

Methyl ethyl ketone 170

Methyl ethyl sulfide 135

Methyl fluoride 27

Methyl formate 67-69

Methyl hydride 30-31

Methyl hydroxide 32-34

Methyl iodide 28

Methyl i sobutyrate 231

Methyl isopropyl ketone 229

Methyl i sothi ocyanate 58

Methyl ketone 112-114

Methyl mercaptan 34-35

Methyl methanoate 67-69

Methyl monosulfide 89

Methyl mustard oil 58

Methyl nitrite 30

Methyl phenyl ether 337

Methyl phenyl ketone 363

Methyl pivalate 309

Methyl propanoate 178

Methyl propionate 178

Methyl propylate 178

Methyl sulfide (8CI) 89

Methyl sulfocyanate 58

Methyl sulfoxide (8CI) 87

Methyl tert-butyl ether 237

Methyl tert-butyl ketone 308

S - Methyl thioacetate 118

Methyl thiocyanate 58

Methyl thi o i socyanate 58

Methyl tri fluoride 18

Methyl tr i f luoroacetate 97

Methyl trimethylacetate 309

Methyl 2-methylpropanoate 231

Methyl 2-methyl prop i onate 231

Methyl 3-pyridyl ketone 331

Methyl 4-pyridyl ketone 332

p-Methyl-. alpha. -methyl styrene 404
Name Index

530

4-Methyl-. alpha. -methylstyrene 404

N-Methyl-. delta. -valerolactam 301

Methyl -d3 ether 44

N-Methyl-N-ethylami ne 140-141

N-Methyl-N-ethylan i 1 i ne 395

m-Methyl-N » N-di met hylani line 394

2-Methyl- 1-butene 224-225

1-

Methyl- 1 -eye 1 opentene 295

2-

Methyl - 1 -pentene 306

1-

Methyl- 1 -phenyl ethylene 387

2-

Methyl- 1-propene 161-162

1-Methyl-1,2-dihydro-2-pyridinone

1-Mathyl~2( 1H)-pyri di none 286

1

Methyl-2 ( 1 H

) -pyr i done 286

2-

Methyl-2-ami nopropane 195

3-

Methyl-2-butanone . 229

2-

Methyl-2~butene 223

3-

Methy 1-2-butene 223

2-Methyl-2-methoxypropane 237

( E

) -3~Methyl-2-pentene 304

trans-3-Methyl-2-pentene 304

2-Methy 1-2-pentene 305

2-flethyl-2-phenylpropane 4 10-41 1 N-Methyl-2-pi per i di none 301

1-Methyl-2-pi per i di none 301

N-Methyl-2-p i per i done 301

1-

Methyl-2-pi per i done 301

2-

Methyl-2~propanethi ol 193

2-

Methy 1-2-propanol

3-

Methy 1-2-propylamine

1 -Methyl -2 -pyr i di none N-Methyl-2-pyri done

1-Met hy 1-2- pyri done

4-

Mathyl~3-pentene

1-Mathyl-4-i sopropenylbenzene 404

4-Methyl~4-pentene 306

Methylacetaldehyde 115-116

Methylacetylene 100

Methylami ne (8CI) 36-37

(Methylami no )acetoni tri le 111

(Methylam i no ) benzene 339

N-Methyl am i noaceton i tr i le 111

192

286

286

305

196

286

Methylami noethane

m-Met hylani line

p-Methylani 1 i ne N-Methy lan i line

3-

Methylan i line

4

Me thy lan i line

N-Methylazi r i di ne 1-Methylaziridine

p-Methylbenzaldehyde

4-Methylbenzaldehyde

m-Methylbenzenami ne p-Methylbenzenami ne N-Methylbenzenami ne

3-

Methylbenzenami ne

4-

Methylbenzenami ne

140-141

341-342

340

339

341-342

340

128

128

364

364

341-342

340

339

341-342

340

286
Name Index

53 1 Methyl benzene 333-336

Methylbenzol 333-336

Methylbutanone 229

Methylcarbi nol 82-83

. alpha . -Methylcyclohexene 352

1 -Methyl cyclohexene 352

1-Methylcyclopentene 295

Methy lcycl opropane 164

5-Methyldeoxyuri di ne 414

Methyl d i ethy lam i ne 240

N~Methyldi ethylami ne 240

Methyldi phenylphosphi ne oxide

Methylene cyanide 96

Methylene difluoride 20

Methylene oxide 21-22

. alpha. -Methylene-diphenylmethane

Methylene, dichloro- (8CI9CI)

Methylene, difluoro- (8CI9CI)

Methylenecyclopentane 296

Methylenedi n i t r i 1 e 96

1 -Methylethanethi ol 134

Methylethylami ne 140-141

N-Methylethylami ne 140-141

1-Methylethylami ne 137

Methy let hylene 107-103

N-Methyl ethyl en i mi ne 128

1 -Methyl ethy len i mi ne 128

Methyl formami de 76

N-Methylformami de 76

8-Methyl quan i ne 290

N-Methyl i mi dazole 156

1 -Methyl i mi dazole 156

Methylmethane 79-80

Methy 1 o 1 32-34

Methylolpropane 191

2-(p-Methylphenyl)propene

Methylphenylami ne 339

N-Methylphenylami ne 339

Methylphosphi ne 38

N-Methylpi peri di ne 311-312

1-

Methylpi per i di ne 311-312

2-

Methylpropanal 169

2-Methylpropanamide 186

1

Methy 1 propanam i ne 200

2-

Methyl propane nitrile 158

2-Methyl propene 161-162

. alpha. -M at hylpropionaldehyde

404

2-Methylpropi onaldehyde

2-Methylpropionitri le

1-

Methylpropylamine

2-

Methylpropylami ne 6-Methylpur i ne 275

.alpha. -Methyl pyridine

•beta. -Met hylpyridine

.gamma. -Methyl pyridine

p-Methylpyr i di ne 281

2-Methyl pyr i d i ne 283

200

196

169

153

283

282

281

427

430

14-15

16

169
Name Index

532

3-Methylpyridine 282

4-Methylpyr i di ne 28 1 N-M ethyl pyrrol i di ne 234-235

1-M ethyl pyrrolidine 234-235

.alp ha. -Methylstyrene 387

. alpha. -Methylstyrol 387

2-Methyltetrahydrofuran 226

N-M ethyl tetrahydropyrrole

(Methylthio)ethane 135

o -Methyl toluene 367 -368

5-Methyluraci 1 216

M i a z i n e 146

M i r b a n e oil 268

Molecular hydrogen 449-451

Molecular oxygen 47 1 -472

Mono-n-butylamine 197

Mono-n-hexylami ne 318

Mono-n-propylami ne 139-140

Monoal lylami ne 126

Monoamylami ne 238

Monobenzylamine 338

Mo nobromo ethane 69

Monobromcmethane 25

Monobutyl amine 197

Monocarbon difluoride 16

Nonochlorethane 70

Monochloroacetonitri le 47

Monochlorobenzene 264-265

Monochloroethane 70

Monochl o r oethano i c acid 5 1 Monochloromethane 26-27

Monochl o romethyl cyanide 47

Monoethylami ne 90

Monof luoroacet i c acid 54

Monofluorobenzene 266-267

Monofluoroethane 71

Monofiuoroethylene 53

Mo no hydroxybenzene 276

Mo nohydroxyme thane 32-34

Monoi odoethane 73

Mcnoi sobutylamine 196

Monoi sopropylamine 137

Monomethylami ne 36- 37

234-235

N-Monomethy Ian i 1 i ne 339

Monomethylf ormami de 76

Monophenol 276

Monopropylamine 139-140

Monopyrrole 152

Morbicid 21-22

Morpholine (8CI9CI) 184

Morton EP- 16 1 E 58

Muriatic acid 440

Muriatic ether 70

My o col 409

Myrmicyl 23-25

MCB 264-265

MEK 170
Name Index

533

Nadone 299

Nako H 292

Naphtol AS~KG 340

Naphtol A5-KGLL 340

Narcotile 70

Natural Pearl Essence

Naturon 215

Nebularine 405

Neopentylami ne (SCI) 242

cotinic acid nitrile

co t i non i t r i 1 e (8CI)

N

N

NNN

NN

N

N

N

NN

N

N

N

N

N

N

NN

N4-Nitro pyridine 210

Nitrosyl radical 469

Nitrous acid, methyl ester

215

262

262

obe oil

trie acid,

trie oxide

trie oxide

t r o - S i 1 t robenzene

trobenzo

1

trocarbol

troethane

t r ogen

trogen

trogen

trogen

trogen

trogen

trogen

trogen

trogen- 1

4

tromethane

365

ethyl ester (8CI9CI)

469

(NO) 469

458-46 1 268

268

29

77

(8CI9CI) 470

f luori de 445

fluoride ( NF3 ) (8CI9CI)

gas 470

monoxide 469

oxide (NO) (8CI9CI) 469

oxide (N20)

tri fluoride

470

29

(8CI9CI

)

445

445

47 1

(8CI9CI)

Ni trous oxi de 47 1 Norbornene 350

2-Norbornene (8CI) 350

Norbornylene 350

2-Norbornylene 350

Norcamphene 350

Norfenchene 350

Norleucamine 238

Norvalami ne 197

Nucleocardyl 409

NSC 65423 405

Obep in 366

Oil of Mi rbane

Oil of Myrbane

Olef i ant gas 59

Optal 132-133

Orange GC base

Orsin 292

Orthamine 291

Orthodiazine 145

0 rthohydrogen 449-451

Osmosol extra 132-133

1 - Oxa-4-aza cyclohexane

Oxacycl obutane 117

268

268

272

184

78

30
Marne Index

534

Oxacycl ohexane 228

Oxacyclopentadi ene 150

Oxacycl opentane 171

Oxa cyclopropane 65

Oxane 65

Oxane 228

2H- 1 , 4-0xazi ne, tetrahydro4H- 1 , 4-0xazi ne, tetrahydroOxetane (9CI) 117

Ox i doethane 65

Oxirane (9CI) 65

Oxirene, di hydro- 65

.alpha.-Oxodiphenylmethane

. alpha . -Oxodi lane 426

Oxolane 1 7 1 Oxole 150

Oxomethane 21-22

6-0xopur i ne 211

2-0xopyr i mi di ne 148

Qxybenzene 276

1 ,

1 ' -Oxybi spropane 313

Oxyfuma 65

Oxyfume 12 65

Oxygen (8CI9CI) 471-472

Oxygen fluoride 444

Oxygen molecule 471-472

Oxygen-16 471-472

Oxymathylene 21-22

Paradiazine 147

Paraform 2 1-22

Parahydrogen 449-451

Pearl Essence 215

Pelagol D 292

Pelagol DR 292

Pelagol Grey D 292

Peltol D 292

Pentaborane 10 Pentaborane CB5H9) 10 PentaboraneC 9) (8CI9CI) 10 Pentacarbonyl iron 202

2 , 4-Pentadi one 220

Pentaf luorobenzene 247

1.2.3.4.5-

Pentafluorobenzene

Pen-tamethy 1 ene oxide 228

Penfame-thylenedi ami ne 245

Pentama-thylen i mi ne 233-234

n-Pentanal 227

Penfanal (9CI) 227

1-Pentanami ne (9CI) 238

1 .

5-

Pentanedi ami ne C8CI9CI)

2 , 4-Pentanedi one (8CI9CI)

184

184

426

247

245

220

222

225

Pentanen i tr i le (9CI)

3-Pentanone (8CI9CI)

1-

Pentene, 2-methyl- (8CI9CI)

2-

Pentene, 2-methyl- (8CI9CI)

2-Pentene> 3-methyl-,

n-Pentylami ne

(E)- (8CI9CI)

238

306

305

304
Name Index

535

1 -Pentylami ne 238

tert-Pentylami ne (8CI) 239

Pentylamine (8CI) 238

Perf luoroacet i c acid 46-47

Perf luoroammoni a 445

Perf luorobenzene 246

Perf luoromethane 17 Petrohol . 131-132

Phene 269-270

Phenethylene 362

Pheni c aci d 276

Phenol

Phenyl

Phenyl

Phenyl

Phenyl

Phenyl

Phenyl

Phenyl

Phenyl

Phenyl

Phenyl

(8CI9CI

)

alcohol

chlor i de

cyani de

f luor i de

hydrate

hydr i de

hydrox i de

ketone

methyl ether

-265

276

276

264-

329

266-267

276

269-270

276

426

337

387

293

291

292

methyl ketone 363

1-

Phenyl-1-methylethylene

2-

Phenyl- 1 -propene 387

Phenylamine 278-280

N-Phenylan i 1 i ne 421

1-Phenylbutane 412-413

1 > 2-Phenylenedi ami ne 291

1 .

3-

Phenyl ened i ami ne 293

1 .

4-

Phenylenedi ami ne 292

m-Phenylenedi ami ne (8CI)

0-

Phenylenedi ami ne (8CI)

p-Phenylenedi ami ne (8CI)

Phenylethane 369-371

1-

Phenylethanone 363

Phenylethene 362

Phenylethylene

Phenyl ic acid

Phenylic alcohol

Phenylmethanal

Phenylmethane

(Phenylmethyl)amine

N-Phenylmethylamine

N-Phenylpi peri dine

1-Phenylpi peri dine

1 - Phenyl propane

2-

Phenylpropane

2-Phenyl propene

.beta.-Phenylpropylene

N-Phenylpyrrolidine

1-Phenylpyrrolidine

. alpha. -Phenylstyrene

Phenyltrimethylmethane

Phosphine CPH3) 462-464

Phosphine (8CI9CI) 462-464

Phosphine oxide, (

1 -methyl ethyl ) di phenylPhosphine oxide, butyldi phenyl- 435

362

276

276

330

333-336

338

339

420

420

390-391

388-389

387

407

407

387

430

410-411

( 9CI

)

432
Name Index

536

decanyldi phenyl- 438

di phenylpropyl- 433

ethyldi phenyl- (8CI9CI)

i sobutyldi phenyl- 434

i sopropyldi phenyl- (8CI)

methyldi phenyl- (8CI9CI)

neopentyldi phenyl- 436

dimethyl- (8CI9CI) 92

methyl- (8CI9CI) 38

trimethyl- (8CI9CI) 142

462-464

oxide,

oxide,

oxide,

oxide,

oxide,

oxide,

oxide.

Phosphi ne Phosphi ne

Pho sph i ne Phosphi ne Phosphi ne Phosphine

Phosphine

Phosphi ne,

Phosphi ne

,

Phosphine,

Phosphorus trihydride

Piazine 147

.alp ha. -Pi coline 283

. beta . -P i co 1 i ne 282

. qamma . -P i col i ne 281

431

m-P i col i ne

o-P i col i ne

p-P i co 1 i ne

2 - P i c o 1 i n e

3 — P l coline

4-Picoline

P i co 1 i n i

c

282

283

28 1 (8CI) 283

( 8CI ) 282

(8CI) 281

acid nitrile

Picolinonitrile

P i mel i c ketone

Pimelin ketone

P i nacol i

n

P i nacol i ne Pinacolone

P i perazi d i ne

1,4-Pi perazi ne Piperazine

Piperidine

Piperidine,

Piperidine,

Piperidine,

2-Piparidinone,

2-P i per i done , 1

263

( 8CI 263

)

299

299

308

308

308

183

188

(8CI9CI) 188

(8CI9CI) 233-234

1-methyl- (8CI9CI)

1-

phenyl- (8CI9CI)

2-

methoxy- 302

1-methyl- (9CI)

methyl- (8CI)

P i per sol 188

P i r od 149

Pivalic acid, methyl ester (8CI)

Potassa 448

Potassium hydrate 448

Potassium hydroxide (8CI9CI)

Praval 439

311-312

420

30 1 30 1

309

448

10 1

Prolami ne Pronarcol

Propadi ene

1 , 2-Propadi ene Propaldehyde

n-Propan-1-ol

n-Propan-2-o

1

Propanal (9CI)

Propanal, 2-methyl- C9CI) 169

Propanamide, 2-methyl- (9CI) 186

1

P ropanam i ne (9CI) 139-140

2-

Propanami ne (9CI) 137

2-Propanami ne, N-( 1-methylethyl )- C9CI)

182

189-190

10 1

( 9CI

)

1 15-1 16 132-133

131-132

1 15- 1 16

317

432

427
Name Index

537

2-Propanam i ne , N-( 1 » 1-di methylethyl )-2~methyl- C9CI)

2-Propanami ne, N-ethyl- (9CI) 243

2-Propanami ne, N-ethyl-N-( 1 -methylethyl )- (9CI) 38 1 1-Propanami ne, N-propyl- (9CI) 320

1-

Propanami ne, N,N-diethyl- (9CI) 356

2-

Propanami ne» N , N~d i methyl- (9CI) 241

1-

Propanami ne, N / N~d i propyl - (9CI) 399

2-

Propanami ne/ N / N / 2~tr i methyl- (9CI) 321

1-Propanami ne/ N z N z 2 z 2-tetramethy 1- (9CI) 357

1-

Propanami ne/ 2-methyl- (9CI) 196

2-

Propanami ne/ 2-methyl- (9CI) 195

1-Propanami ne/ 2-methyl -N- ( 2-methyl propyl ) - (9CI)

1-Propanami ne/ 2 f 2 — d i methyl- (9CI) 242

1-Propanami ne/ 3 z 3 / 3~t r i f luoro- (9CI) 108

n-Propane 130-131

Propane (8CI9CI) 130-131

. a 1 pha ./. gamma . -Propane oxide 117

1, I'-oxybis- ( 9CI ) 313

1, I’-thiobis- ( 9CI ) 315

1 / 3-epoxy- 1 1

7

Propane/ 2-ethoxy- (9CI) 236

Propane/ 2-ethoxy-2~methyl- (9CI) 314

Propane/ 2-methoxy-2-methyl~ (9CI) 237

Propane/ 2z2'-oxybis- (9CI) 312

Propane/ 2 z 2 ' -thi obi 5- (9CI) 316

Propane/ 2 / 2 ’ -th i ob i £[ 2-methyl- (9CI) 377

1 / 3-Propanedi ami ne (8CI9CI) 143

1 / 3-Propanedi ami ne/ N / N-d i methyl - (8CI9CI) 244

1 / 3-Propanedi ami ne f N , N / N

' / N ' -tetramethyl- (8CI9CI)

Propanedi n i tr i le (9CI) 96

Propanen i tr i le (9CI) 104

Propanethi ol

Propane

Propane

Propane

2-methyl- (9CI) 158

3~am i no- ( 9CI

)

1 1 1 3-chloro- ( 9CI

)

103

134

(8CI9CI) 134

(8CI9CI) 134

2-methyl- (8CI9CI) 193

( 9CI ) 119

methyl ester (9CI) 178

2-methyl-/ methyl ester ( 9CI

)

231

Propanoic acid/ 2 , 2 — d i methyl- z methyl ester (9CI)

n-Propanol 132-133

1-

Propanol (9CI) 132-133

2-

Propanol (9CI) 131-132

2-Propanol/ 2-methyl- (9CI) 192

Propanone 112-114

2-Propanone (9CI) 112-114

2-Propanonez acetyl- 220

Propargyl ether 277

Propargylami ne 105

2-P ropen- 1 -am i ne (9CI) 126

2-Propen- 1-ami ne/ N-2-propenyl- (9CI) 300

2-Propen- 1-ami ne/ N z M — d

i -2-propenyl- (9CI) 398

Propene (8CI) 107-108

1-Propene (9CI) 107-108

Propene/ 2-cyclopropyl- (8CI) 297

382

378

358

309
Name Index

538

Propene, 2-methyl- (8CI) 161-162

1-Propene, 2-methyl- (9CI) 161-162

1-Propene, 2-phenyl- 387

1-Propene, 3,3'-oxybis- (9CI) 300

Propenen i tr i le 99

2~P ropenen i tr i le C9CI) 99

Propine 100

Prop i onal 115-116

Propi onaldehyde (8CI) 115-116

Propi one 225

Propionic acid (8CI) 1 19

Propionic acid, methyl ester (8CI) 178

Propionic aldehyde 1 15-116

Propionic nitrile 104

Propi oni tri le (8CI) 104

Propi oni tri le, 3-amino- (8CI) 1 1 1 P r op i on i t r i 1 e , 3-chloro- (8CI) 103

Propi ononi tri le 104

Propol 131-132

n-Propyl acetate 230

Propyl acetate 230

1-Propyl acetate 230

n-Propyl alcohol 132-133

sec-Propyl alcohol 131-132

Propyl alcohol (8CI) 132-133

Propyl carbinol 19 1 Propyl cyan i de 159

Propyl ether (8CI) 313

n-Propyl formate 173-174

Propyl formate 173-174

Propyl hydride 130-131

n-Propyl mercaptan 134

Propyl mercaptan 134

Propyl methanoate 173-174

Propyl monosulfide 315

Propyl sulfide (8CI) 3 15

Propyl tr i f luoroacetate 217

Propylaldehyde 115-116

n-Propylam i ne 139-140

sec-Propylamine 137

1-Propylami ne 139-140

2-Pro pylamine 137

Propylamine (8CI) 139-140

Propylamine, N-tert- butyl-1, 1-dimethyl- ( 8CI

)

Propylamine, N,M -diethyl- (8CI) 356

Propylamine, N,N,2,2 -tetramethyl- (8CI) 357

Propylamine, 3 , 3 , 3~tr i f luoro- (8CI) 108

n-Propylbenzene 390-391

Propylbenzene 390-391

1-Pro pylbenzene 390-391

Propylene 107— 108

1-Propylene 107— 108

1 , 3~P r opyl ene oxide 1 17

1, 3-Pro pylenedi amine 143

1, 3-Pro pylenimine 127

Propylic alcohol 132-133

Propylic aldehyde 115-116

400
Name Index

539

1 -Propylmercaptan 134

2-Propylmercaptan 134

Propylni tr i le 104

2-Propyn- 1-ami ne (9CI) 105

2-Propyn- 1-ami ne, N-2-propyny 1 - (9CI) 284

2-Propyn- 1-ami ne, N , N~d i -2-propynyl- (9CI) 386

Propyne (8CI) 100

1-Propyne (9CI) 100

1-

Propyne, 3»3'-oxybis- (9CI) 277

2-

Propynyl ether (8CI) 277

2-Propynylami ne (8CI) 105

Prozo in 119

Prussic acid 19-20

Pseudoacetic acid 119

Pseudobutylbenzene 410-411

Pseudoestragole 406

Pure oxygen 471-472

9H~Puri n- 1-ami ne, 9-cyclopentyl- (9CI) 408

Puri n-6( 1H)-one 211

9H~Pur i n~6 ( 1 H

) -one 211

Pur i n~6 ( 3H ) -one 211

1H-Purin-6-amine C9CI) 214

9H-Pur i n~6 -am i ne , 9- . beta . -D-r i bofuranosyl- 409

Puri n-6-ol 2 1 1 3H-Purin-6-ol 211

9H-Purin-6-ol 211

6H~Puri n-6~one, 1,7-dihydro- (9CI) 211

6H-Pur i n-6-one , 2~ami no- 1 , 7-di hydro- (9CI) 215

6H~Pur i n-6-one, 2~ami no- 1 , 7 — d i hydro~8-methyl- (9CI)

Purine r i bonucleosi de 405

Purine riboside 405

Purine, 6-chloro- (8CI) 203

IH-Purine, 6-chloro- C9CI) 203

Purine, 6-methyl- (8CI) 275

IH-Purine, 6-methyl- (9CI) 275

9H~Purine, 9-.beta.-D-ribofuranosyl- (8CI9CI) 405

Puri nosi ne 405

Putresci n 201

Putresci ne 201

2H-Pyran, tetrahydro- (8CI9CI) 228

Pyrazine (8CI9CI) 147

Pyrazine hexahydride 188

Pyrazine, hexahydro- 188

Pyridazine (8CI9CI) 145

4-Pyr i di nami ne, N , N~d i methyl- (9CI) 351

Pyridine (8CI9CI) 212-213

Pyridine, hexahydro- 233-234

Pyridine, 2- ( tr i f luoromethyl ) - (8CI9CI)

Pyridine, 2-chloro- (8CI9CI) 204

Pyridine, 2-fluoro- (8CI9CI) 208

Pyridine, 2-methoxy- (8CI9CI) 287-288

Pyridine, 2-methyl- C9CI) 283

Pyridine, 2,4-dimethyl- (9CI) 343

Pyridine, 2,5-dimethyl- (9CI) 345

Pyridine, 2,6-bi s( 1 , 1-di methylethyl )- (9CI)

Pyridine, 2 , 6-di -tert-butyl- (8CI) 429

Pyridine, 2,6-dimethyl- (9CI) 344

258

429

290
Name Index

- 540 -

Pyri di ne,

Pyridine,

Pyridine,

Pyridine,

Pyridine,

Pyridine,

Pyri dine.

Pyridine,

Pyri d i n e

,

Pyridine,

Pyri dine.

Pyridine,

Pyri dine.

3-(trifluoromethyl)- (8CI)

3-chloro- (8CI9CI) 205

3-fluoro- (8CI9CI) 207

3-methoxy- (8CI9CI) 289

3-

methyl- (9CI) 282

3,5-dimethyl- (9CI) 346

4-

( di methylami no ) - C8CI)

4-(tri fluoromethyl)- (8CI9CI)

4-chloro- (8CI9CI)

4-fluoro- (8CI9CI)

4-methoxy- (8CI9CI)

4-methyl- (9CI)

4-nitro- (8CI9CI)

2-

Pyri di necarboni tri le (9CI)

3-

Pyri di necarboni tri le (9CI)

4-

Pyri di necarboni tri le (9CI)

2 ( 1 H

) -Pyr i di none , 1-methyl- (9CI)

2 ( 1 H ) -Pyr i done , 1-methyl- (8CI)

3-

Pyridyl methyl ketone 331

4-

Pyri dyl methyl ketone 332

2-

Pyridyl nitrile 263

3-

Pyri dylcarboni tri le

Pyrimidine (8CI9CI) 146

2 .

4-

Pyr i mi di nedi ol 149

2.

4-

Pyri midinedione 149

206

209

281

210

263

262

26 1

262

259

351

260

285

286

286

2,4( 1H,3H)-Pyrimidinedione (9CI) 149

2,4( 1H,3H)-Pyrimidinedione, di hydro-1-. beta. -D-ribofuranosyl- 397

2,4C1H,3H)-Pyrimidinedione, 1-(2-deoxy-.beta.-D-erythro-pentofuranosyl

4 14

2 , 4 ( 1 H , 3H ) -Pyr i m i di ned i one , 5-methyl- (9CI) 216

2-Pyri mi di nol 148

2-Pyri mi di none 148

2 ( 1 H

) -Pyr i mi d i none (8CI9CI) 148

2( 1H)-Pyr i mi di none, 4-amino- (9CI) 155

2( 1H)-Pyr i mi di none, 4~ami no- 1- . beta . -D-r i bofuranosyl- 396

2( 1H)-Pyrimi done 148

2-Pyri mi done 148

Pyroacetic ether 112-114

Pyrobenzol 269-270

Pyrobenzole 269-270

Pyrod 149

Pyrrol 152

Pyrrole (8CI) 152

1 H-Pyr role (9CI) 152

Pyrrole, tetrahydro- 182

Pyrrolidine (8CI9CI) 182

Pyrrolidine ring 182

Pyrrolidine, 1-methyl- (8CI9CI) 234-235

Pyrrolidine, 1-phenyl- (8CI9CI) 407

PRO 131-132

Quinuclidine (8CI) 354-355

R 23 18

R 290 130-131

Renal PF 292

.beta.-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy- 409

. beta . -D-Ri bofuranosi de, adenine-9 409

. beta . -D-Ri bofuranosi de, cytosine-1 396
Name Index

- 541 -

. beta . -D-R i bof uranos i de , -thymine-1 2-deoxy- 414

.beta.-D-Ribofuranoside, 2 > 4 ( 1H,3H)-pyrimidinedione~1

9-( .beta.-D-Ribofuranosyl)purine 405

9-.beta.-D-Ribofuranosyladenine 409

1-. beta. -D-Ribofuranosyl cytosine 396

9- . beta . -R i bof urano sylpur i ne 405

l-.beta.-D-Ribofuranosyluracil 393

Ri bosylpuri ne 405

Rohrputz 449

Rchrrei n i ger Rofix 449

Salzsaeure 440

Sandesin 409

Santoflex LC 292

Sarc i ne 211

Sarcosi noni tr i le 111

Sark i n 211

Sark i ne 211

Selane 457

Selenium hydride 457

Sextone 299

Silane (8CI9CI) 465

Silicane 465

Silicon hydride (SiH4) 465

Silicon tetrahydride 465

Sodium hydrate 449

Sodium hydroxide (8CI9CI) 449

Solvent ether 189-190

Somipront 87

Spirit of Hartshorn 458-461

Stella Polaris 215

Stink damp 454-456

Styrene (8CI) 362

. alpha . -methyl- (8CI) 387

p-chloro- . alpha . -methyl- C8CI) 384

p-fluoro- . alpha . -methyl- (8CI) 385

p-methoxy- . alpha . -methyl- 406

p, . alpha . -di methyl- (8CI) 404

362

362

Styrene

Styrene

Styrene

Styrene

Styrene

,

Styro

1

Styro 1

e

Styrolene 362

Styropol SO 362

Sulfide, ethyl methyl

Sulfinylbismethane

Sulfur fluoride (SF6)

fluoride ( SF6

)

hexaf luori de

Sulfur

Sulfur

Sulfur

Sulfur

Sulfur

( 8CI ) 135

87

(8CI) 446

(OC-6-11)- ( 9CI

)

446

446

hydride 454-456

oxide ( SO 3 ) 473

trioxide (8CI9CI) 473

Sulfureted hydrogen 454-456

Sulfuric anhydride 473

Sulfuric ether 189-190

Superlysof orm 21-22

SD Alchol 23-hydrogen 82-83

S03 473

SQ 9453

Tak i neocol

87

131-132

393
Name Index

542

Tecsol 82-83

Terabol 25

Terephthala ldehydon i tr i le (8CI) 361

Tereton 120-121

Tert ra 1 D , 292

TetraboraneC 10) C8CI9CI) 9 Tetraborane(8 ) 8

1 . 2 . 3 .

4-

Tetraf luorobenzene 249

1 . 2 . 3 .

5-

Tetraf 1 uorobenzena 250

1 , 2 > 4 , 5-Tetraf luo robenzene 248

1 . 2 . 4 .

6-

Tetraf luorobenzene 250

1 . 3 . 4 .

5-

Tetraf luorobenzene 250

2 . 3 . 4 .

5-

Tetraf luorobenzene 249

2 . 3 . 5 .

6-

Tetraf luorobenzene 248

Tetraf luoromethane 17 Tetrahydro-p-oxazi ne 184

Tetrahydro- 1 , 4-oxazi ne 184

Tetrahydro~2-methylfuran 226

Tet rahydro-2H~pyran 228

Tetrahydro-2H- 1 , 4-oxazi ne 184

Tetrahydrofuran 171

Tetrahydropyran 228

Tetrahydropyrrole 182

Tetrahydrosyl van 226

N , N , N

1 ,N'-Tetramethyl-1,2-diaminoethane 322

NjNjN'jN'-Tetramethyl-l^-ethanediamine 322

N , N , N ' ,N'-Tetramethyl-1,3-diaminopropane 358

N,N,N' ,N'-Tetramethy 1-1, 3-pro pa nediamine 358

N , N , N ' ,N T -Tetramethyl-1,4-butanediamine 383

N,N,N’,N'-Tetramethyl-1,4-diaminobutane 383

N , N , N ' ,N’-Tetramethyl-1,6-diaminohexane 418

N,N,N , ,N f -Tetramethyl-1,6-hexanediamine 418

2,2,4,4-Tetramethyl-3-thiapentane 377

NjN.N’jN'-Tetramethylbutanediamine 383

.alpha. , .delta. -(Tetramethyldiamino)butane 383

Tetramethyldi ami nobutane 383

Tet ramethyl d i am i no ethane 322

Tetramethylene oxide 171

Tet ramethyl ened i am i ne 201

Tetramethylenimine 182

NjN/N’jN'-Tetramethylethanediamine 322

N , N , N ' ,N'-Tetramethylethylenediamine 322

NjNjNVN'-Tetramethylhexamethylenediamine 418

Tetramethylprcpanedi ami ne 358

Tetramethylputresc i ne 383

NjNjN'.N'-Tetramethyltetramethylenediamine 383

N,N,N' ,N'-Tetramethyltri met hylenedi amine 358

Tet role 150

2-Thiabutane 135

4-Thi aheptane 3 15

3-Thi apantane 194

2-Thi apropane 89

Th i ocyan i c acid. methyl ester (8CI9CI) 58

Thi oethano

1

88

Thioethyl alcohol 88

Thioethyl ether

Thymi din 414

194
Name Index

54 3 Thymidine (8CI9CI) 414

Thymin (purine base) 216

Thymine (8CI) 216

Thymi ne-2-desoxyr i bosi de 414

Thymi nedeoxyr i bosi de 414

4-Tolualdehyde 364

p-Tolualdehyde (8CI) 364

p-Tolualdehyde, . alpha .,. alpha .

,

Toluene (8CI) 333-336

3-

Tolui di ne

4-

Tolu i di ne m-Tolui di ne p-Toiui di ne m-Tolui di ne. Toluol

p-Toluyl aldehyde

p-Tolyl aldehyde

p-Tolylamine 340

2-p-Tolylpropene

Trapex 58

Trapexide 58

Tri (methyl-d3)amine

Tri-n-butylamine

Tri-n-propylamine

Tri -2-pro pynylamine

Tr i al lylami ne (8CI)

s-T r i azaborane

. a lpha . -t r i f luoro- (8CI)

341-342

340

( 8CI ) 341-342

( 8CI ) 340

N > N-di methyl- (8CI)

333-336

364

364

404

394

95

425

399

( 8CI

)

398

7

386

1 , 3 , 5 , 2 , 4 , 6-Tr i azatr i bor i ne , hexahydro- 7 Tr i bor i netr i ami ne 7 Triboron nitride 7 Tr i butylam i ne (8CI) 425

Tr i chlorethanol 52

Tri chloroacetoni tr i le 43

. beta . -Tr i chloroethanol 52

Tr i chloroethanol 52

2, 2, 2-Tri chloroethanol 52

2 , 2 , 2~Tr i chi oroethyl alcohol 52

Tr i chloromethyl cyanide 43

Tr i ethylami ne (8CI) 319

Tr i ethylami ne , 1 ,

1 ' -di methyl- (8CI) 38 1 Tr i ethylenedi ami ne 307-308

.alpha. , .alpha. , .alpha.-Trifluoro-p-tolualdehyde

Tr i f luoroaceti c acid 46-47

Tr i f luoroami ne 445

Tr i f luoroammon i a 445

sym-Tr i f luorobenzene 252-253

1 . 2 .

4-

Tr i f luorobenzene 251

1 , 2 , 5~Tr i f luorobenzene 251

1 , 3 , 4-Tri f luorobenzene 251

1 , 3 , 5-Tri f luorobenzene 252-253

Tr i f luoroborane 4 Tr i f luoroboron 4

4 . 4 .

4-

Tr i f luorobutylami ne 167 , Tr i f luoroethano i c acid 46-47

2 , 2 , 2~Tr i f luoroethanol 55

Tr i f luoroethene 45

. beta beta .,. beta . -Tr i fluoroethyl alcohol 55

360

360
Name Index

- 544 -

2 , 2 , 2~Tr i f luor oethyl alcohol 55

2 , 2 , 2~Tri f luoroethyl -formate 98

(2,2,2-Trifluoroethyl)dimethylamine

Tr i f luo roethylami ne 61-62

2

,

2 , 2~Tr i f luoroethylami ne 61-62

Tr i f luoroethylene 45

Tr i f luoromethane 18

p-(TrifIuorcmethyl)benzaldehyde 360

4-(Trifluoromethyl)benzaldehyde 360

2~(Tr i f luoromethyl )pyri di ne 258

4

- ( T r i f 1 uo r omethy 1 ) py r i d i ne 260

3 , 3 , 3~Tr i f 1 uo ropropylami ne 108

Trimethyl(dimethylaminomethyl)silane

T r i methylami ne (8CI) 138-139

Tri methylami ne~d9 (8CI) 95

Tr i methylami ne, ( tr i methyl 5 i lyl ) - (8CI)

Tr i methylami nomethane 195

m,N,N-Trimethylaniline 394

N , N , 3~Tr i methylan i 1 i ne 394

Tr i methylar sen i c 136

Trimethylarsine 136

sym-Tr i methylbenzene 392

1 ,3, 5-Trim ethylbenzene

Trimathylcarbinol 192

Trimethylene 106

Trimethylene (cyclic)

Trimethylene oxide (SCI)

Tr i tnethy lened i ami ne 143

T r i methyl en i mi ne 127

Tr i mcthylethylene 223

1 , 1 , 2~Tr i methylethylene 223

Tr i methylmethanol 192

Tr i methyl phenylmethane 410-411

392

106

1 17

Trimethylphosphine

Trimethylphoephorus

Tr i phenylami ne (8CI)

Triproparqylamine

Tripropylamine (SCI)

Tri 5-n-butylamine

T r i t o x 4 3 Tropex 58

Tutane 200

THF 171

THP 228

TMEDA 143

142

142

437

386

399

425

Unsymmetr i cal di methylhydrazi ne 93

Ura 149

Uracil (SCI) 149

Uraci 1, l-.beta.-D-ribofuranosylUranium (8CI9CI) 474

Uranium I (238U) 474

Uranium-238 474

Urd 393

U r i d i n 3 9 3

. beta . -Ur i d i ne 393

Uridine (8CI9CI) 393

Uridine 2 ' , 3 ' -aceton i de

166

324

324

393

422
Name Index

545

227

227

222

227

Uridine, 2

' -deoxy-5-me-thy 1- 414

Uridine, 2' , 3 ' -0-( 1-methylethylidene)-

Uridine, 2 ' , 3 ’ -0- i sopropy 1 i dene- (8CI)

Uridine, 5,6-dihydro- (9CI) 397

Ursol D 292

Uv i Ion 188

UDMH 93

Valamine 196

Valeral 227

n-Valeraldehyde 227

Va 1 era 1 dehyda (8CI)

Valerianic aldehyde

Valeric acid aldehyde

Valeric aldehyde 227

Va 1 eron i tr i 1 e (8CI)

Valerylaloehyde 227

Ventox 99

Versnel ler NL 63/10 375-376

Vinegar acid 66~67

Vinegar naphtha 176-177

Vinyi cyanide 99

V i nyl f luor i de 53

Vinylbenzene 362

Vinylbenzol 362

Vi nylcyclopropane 218

V i nyl cycl propane 218

Vinylidene difluoride

Vinylidene fluoride 48

Vitamin B4 214

VCN 99

Water (8CI9CI) 451-453

Water vapor 451-453

Watei—d2 (9CI) 442

Watei—2H2 442

Water, heavy (D20) (8CI)

C9CI)

422

48

442

White caustic

Wood alcohol

Wood ether

Worm-A-Ton

Wurmi razi

n

WN 12 58

Xenon (8CI9CI)

1 .

2-

Xylene

1 .

3-

Xylene

1 .

4-

Xylene

m-Xylene (8CI)

o-Xylene (8CI)

p-Xylene (8CI)

p-Xylene-d6

m-Xylol 373

o-Xylol 367-368

p-Xylol 372

Zoba Black D 292

449

32-34

84-86

188

188

475

367-368

373

372

373

367-368

372

359

422
U.S. DEPT. OF COMM.

BIBLIOGRAPHIC DATA

SHEET

1. PUBLICATION OR REPORT NO. NBSIR 79-1777

2.Gov*L Accession No.

W‘

‘ -V v

' ‘ • ..

'Vv

3. Recipient's Accession No.

4. TITLE AND SUBTITLE

A Compendium of Gas Phase Basicity and Proton Affinity

_illeasnraments

5. Publication Date July 1979

^.Performing Organization Code

7. AUTHOR(S) N. Hartman, S. Lias, P. Ausloos, H. M. Rosenstock

S. S. Schroyer, C. Schmidt, D. Martinsen, & G. W. A. Milne

8. Performing Organ. Report No.

9. PERFORMING ORGANIZATION NAME AND ADDRESS

NATIONAL BUREAU OF STANDARDS

DEPARTMENT OF COMMERCE

WASHINGTON, DC 20234

i^ f^lecLT-ask/Work Unit No.

11. Contract/Grant No.

12. SPONSORING ORGANIZATION NAME AND COMPLETE ADDRESS (Street, City, State, ZIP)

same as above.

13. Type of Report & Period Covered April 1979

14. Sponsoring Agency Code

15. SUPPLEMENTARY NOTES

|

1 Document describes a computer program; SF-185, FIPS Software Summary, is attached.

16. ABSTRACT (A 200^word or leas factual summary of moat significant information. If document includes a significant bibliography or

literature survey, mention it here.) Literature values of experimental measurements, calculations and estimations of gas

phase basicities and proton affinities are presented. Where appropriate they are recalculated to common values for the proton affinity of ammonia and

the heat of formation of the proton. The annotated information is ordered by

molecular formula following the Hill System. Indices are given to permit location

of information of by numerical value of the measurement (s) , the compound formula,

name and synonym, and CAS Registry Number. The literature coverage is essentially

complete through 1977.

17. KEY WORDS (six to twelve entries; alphabetical order; capitalize only the lir&t letter of the first key word unless a proper name;

separated by semicolons)

. 18. AVAILABILITY Unlimited 19. SECURITY CLASS

(THIS REPORT)

21. NO. OF

PRINTED PAGES

| | For Official Distribution. Do Not Release to NTIS UNCLASSIFIED

562

P j Order From Sup. of Doc., U.S. Government Printing Office, Washington, DC

20402, SD Stock No. SN003-003-

20. SECURITY CLASS

(THIS PAGE)

22. Price

jCXj Order From National Technical Information Service (NTIS), Springfield,

VA. 22161 UNCLASSIFIED

$16.25

USCOMM-DC