NAT'L INST. OF STAND & TECH

AlllDb tiosm

NBSIR 76-1061

An Annotated Bibliography on

Proton Affinities

K. Hartman

S. Lias

P. J. Ausloos

H. M. Rosenstock

Institute for Materials Research

National Bureau of Standards

Washington, D. C. 20234

April 1976

Final

Issued July, 1976

QC

100

.U56

76-1061

1976

Prepared for Mational Heart, Lung and Blood Institute

Mational Institutes of Health

Bethesda, Md. 20014

NBSIR 76-1061

AN ANNOTATED BIBLIOGRAPHY ON

PROTON AFFINITIES

K. Hartman

S. Lias

P. J. Ausloos

H. M. Rosenstock

Institute for Materials Research

National Bureau of Standards

Washington, D. C. 20234

April 1976

Final

Issued July, 1976

Prepared for National Heart, Lung and Blood Institute

National Institutes of Health

Bethesda, Md. 20014

U.S. DEPARTMENT OF COMMERCE, Elliot L. Richardson, Secretary

Edward O. Vetter, Under Secretary

Dr. Betsy Ancker-Johnson, Assistant Secretary for Science and Technology

NATIONAL BUREAU OF STANDARDS, Ernest Ambler, Acting Director

An Annotated Bibliography on Proton Affinities

K.'Hartman, S. Lias, P. J. Ausloos, H. M. Rosenstock

Institute for Mater ialsr Research

National Bureau of Standards

Washington, D. C. 20234

Abstract

This bibliography consists of approxim-ately 150 references about

proton affinities which cover the period from 1932 through 1975. Included are experimental determinations of proton affinities in the gas phase (through

observation of proton transfer reactions, ion-molecule equilibria, and

appearance potential measurements) as well as determinations from crystal

lattice energies and other miscellaneous techniques. Also included are reviews concerned with or related to proton affinity determinations.

Key words: Appearance potential; basicity; bibliography; heat of formation;

ion-molecule equilibrium; proton affinity; proton transfer

1
Introctuc t ion

During the past twenty years, major advances have been made in the

understanding of the chemical reactions of ions in the gas phase. An

important outgrowth of this work is a growing body of information about gas

phase acidities and basicities. The scale of gas phase basicities is usually

quantified in terms of the proton affinities of the molecules. The proton

affinity is defined as the negative of the enthalpy change resulting from the

addition of a proton to a base to form the conjugate acid. This definition

was originally formulated to express the basicities of molecules in solution.

This field-'of research has developed to the point that areas of

potential scientific usefulness are becoming defined. For example, the scale

of gas phase basicities is now being used as a reference scale against which

to examine, define, and ultimately understand and control solvent effects on chemical equilibria and reactivity. A practical application of the proton

affinity scale is its usefulness for selecting appropriate reagent gases for

use in the analytical application of ion-molecule reactions known as "chemical ionization mass spectrometry" which is finding widespread

application in biochemical and biomedical studies. Finally, through proton

affinity measurements there now exists ion the rmoc hemical information which

ultimately must be brought into accord and combined with the much larger body

of ion thermochemical information derived from spectroscopic and appearance

potential measurements. In fact, this new body of proton affinity

measurements imparts for the first time a network character to ion

thermochemical information, thus posing opportunities for searching tests of

the accuracy of various experimental measurements and their interpretation in

terms of thermochemical quantities.

Scope of Bibliography

This bibliography is intended to cover the literature concerned with

gas phase proton affinities of neutral molecules from the earliest papers on the subject until the cut-off date of December 31, 1975.

In principle, there are two ways to define the scope of a bibliography on proton affinities. 0ne could include every paper whose

results directly or indirectly give information which can be related to

proton affinities, even though the authors did not specifically interpret

their results in those terms. Alternatively, one can simply limit the

bibliography to work which specifically concerns itself with proton

affinities. We have chosen the latter course even though in doing so we may

be neglecting to mention certain studies which contribute useful data. The user of this compilation will be able to locate pertinent related data

through the references listed in the papers of the bibliography. To include

all of these related papers in the bibliography itself would mean including a large fraction of the literature on appearance potential measurements of

hydro gen -cont ai ning ions. A separate comprehensive compilation of these

measurements will appear shortly. Many of these articles would be of only

peripheral interest to the subject of proton affinities.

We also include a list of review articles and papers which discuss

factors relating to proton affinities. Theoretical calculations are not

included.

Presentation of Bibliography

The main body of the bibliography consists of a numbered list of

papers, subdivided into five categories. These are: (X) experimental

determinations of proton affinities based on ion-equilibrium measurements, or

2
limits on proton affinities based on the occurrence (or non -occ urrence ) of

ion-molecule reactions, or on determinations of crystal lattice energies; (Y)

experimental determinations of proton affinities based on appearance

potential measurements; (Z) experimental determinations of proton affinities

through miscellaneous approaches unrelated to those of the first two

categories; (0) derivations of proton affinities through empirical

relationships to other quantities such as ionization potentials or core electron binding energies; (R) selected reviews and papers which present

related and background information.

For each paper we list the molecules corresponding to the proton

affinities determined in that paper. In cases where bracketing techniques or proton transfer equilibria are used to generate proton affinities, we list

not only the species whose proton affinity has been determined, but also the

reference molecules.

In addition, we present a list sorted according to chemical species.

Here again, we give both the molecule whose proton affinity is determined and

any reference species used in the determination. The order of presentation of

the molecules is that of increasing atomic number and molecular complexity.

An author index is also included.

Literature Search

Literature references were obtained initially both by a computer

search for Chemical Abstracts entries on proton affinities going back to

1970, and also by an issue -by- i ssue search of the following major journals,

going back to I960:

Journal of Chemical Physics

Journal of Physical Chemistry

Journal of the American Chemical Society

Journal of Research of the National Bureau of Standards

The International Journal of Mass Spectrometry and Ion Physics

International Journal of Chemical Kinetics

Canadian Journal of Chemistry

Chemical Physics Letters

Transactions of the Faraday Society

Additional entries were found by cross-referencing articles referred to in

reviews and papers of interest.

Acknowledgeme nt s We are grateful to Mrs. Candyce L. Schmidt for her skillful

assistance in all phases of the preparation of this document, to Mr. K. Draxl

and Mr. J. G. Koch who provided helpful information on searching and document

preparation, to Dr. L. W. Sleek for his assistance in the literature search,

and to Dr. G. W. A. Milne of the National Institutes of Health for his help

and encouragement.

3
References

Chong, S. L. , Myers, R. A. Jr., and Franklin, J. L.

,

Proton Affinity of Water, J. Chem. Phys. 56, 2427 (1972).

H2 6, HC06H, d

2

s, h2 s

Cotter, R. J., and Koskl, W. S., Reaction of D

3 6* with

D

2

: Proton Affinity of Water, J. Chem. Phys. 59_,

7 84 ( 1 573 ).

D 2 f, Hg*9

Long, J., and Munson, B. , 6n the Proton Affinity of Water,

J. Chem. Phys. 53, 1355 ( 1 970 ).

H? 0, C3 H6

, cis-2- C4 Hp . (Cfl( 3 ) 2

Cfl, HCHPt, CjH^, CH 3 «H

DePaz, M. , Leventhal, J. J., and Friedman, L. , Tandem

Mass-Spectrometer Study of D3O and Solvated Derivatives

J. Chem. Phys. 5_1, 3748 ( 1969 ).

D? 3, H2 6

Hoi tz, D. , and Beauchamp, J. L., Relative Basicity of Phosphine

and Ammonia in the Gas Phase, J. Am. Chem. Soc . 9_1_, 5913

( 1 969 ).

NH3 , PH3 , (CH3

) 2 C6, CH3

CH<3, H2 6, C2 Ha , CH4

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).

C6. N2 6, CH4 , C62 , CF4

, NCJ, N 2 , H2 , &

2

, Ar

Hemsworth, R. S. , Rundle, H. W., Bohme, D. K. , Schiff, H. I.,

Dunkin, D. B. , and Fehsenfeld, F. C,

Determination of Proton Affinity from the Kinetics

of Proton Transfer Reactions. III. The Measurement of the
Equilibrium Constant at Various Temperatures, J. Chem.

Phys. 59, 6 1 ( 197 3 ).

CH4 , C6 2 , C6, N2 ^

X8 - 71 Chupka, W. A., and Berkowitz, J., Photoioni zati on of

Methane: Ionization Potential and Proton Affinity of CH^,

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

CHA i

X9 - 65 Munson, M. S. B. , and Field, F. H. , Reactions of Oaseous

Ions. XV. Methane 1% Ethane and Methane 1% ProDane,

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

CH4 , C

2 H6

XI 0 - 5 7 Lampe, F. W. , and Field, F. H. , Reactions of Gaseous Ions.

III. Formation of Protonated Methane, J. Am. Chem.

Soc. 79, 4244 ( 1957 ).

CH4

XI 1 - 58 Tal'Pose, V. L. , and Frankevitch, E. L. , Determination

of Proton Affinity and Bond Dissociation Energy by Ion

Impact Method, J. Am. Chem. Soc. 80, 2344 ( 1958).

H2 0, CH-^€5H, CgH^^H, ^2* ^^^.» ^2^6* ^3^8* ^2^4* ^3^6

XI 2 - 69 Haney, M. A., and Franklin, J. L., Mass Spectrometric

Determination of the Proton Affinities of Various

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

CH3 NH2 , NH3 , (CH3

) 2 C6, ( CH3 )g6, PH3 , CH 3CN, CH 3 SH,

CH3CH0, C

6H6 (Benzene), CH3 0H, HC00H, HCN, HgS, HCH0,

H 26, CH 3 Cl, HI, CO, HCl, HBr, CH^

X13 - 72 Cotter, R. J., Rozett, R. VT . , and Koski, Vf. S. , Reactions of

H

2 0* and DgO* with Molecular Hydrogen. I. Proton Affinity

of Hydrogen, J. Chem. Phys. 57, 4100 ( 1972 ).

H2 , D

2
Harris, H. E. , Crowley, M. G. , Grossheim, T. P., Woessner,

P. J., and Leventhal, J. J., Binding Energy of F^, J. Chem. Phys. 59, 6181 ( 1973 ).

Leventhal, J. J., and Friedman, L. , Experimental Determination

of D- Dissociation Energy, J. Chem. Phys. 49, 1974 (1968).

Ridge, D. P., Gas Phase Proton Affinities of Several

Fluoroethylenes, J. Am. Chem. S oc . 97, 5670 ( 1975).

C2 H3 F, CH2 "CF 2

, cls-CHF*CHF, tr ans -CHF'CHF . C

2 HF 3 , H

2 0,

H2S, C2 H5

I, CH3 6H, C2 H4 , CD-gCl, C

2 H

5F, HCH0

Fennelly, P. F. , Hemsworth, P. S., Schiff, E . I., and

Bohme, D. K. , Determination of the Proton Affinity from

the Kinetics of Proton Transfer Reactions. IV. The

Equilibrium OgH* H

2

s* f» 2 and the Relative Proton

Affinity of 0

2 and H2

, J. Chem. Phys. 59, 6405 ( 1973).

0 2 , H2

Beauchamp, J. L., and Buttrill, S. E., Jr., Proton Affinities

of H2 S and H

2 6, J. Chem. Phys. 48, 1783 (1968).

H2 S, H2 0, C2 H4 , C0, CgHpOH

Field, F. H. , and Lampe, F. W., Reactions of Gaseous

Ions. V. Met hane- Hydrogen Chloride and Me thane -Hydrogen

Sulfide, J. Am. Chem. Soc . 80, 5583 (1958).

HCl, H2 S

Hopkins, J. M. , and Bone, L • I., Relative Proton

Affinities of Hydrogen Sulfide and Water, J. Chem.

Phys. 58, 1473 (1973).

H2 0, H2 S

Wei. L. Y . . and Bone. L. I.. Ion-Molecule Reactions
in Methanol and Hydrogen Sulfide, J. Phys. Chem.

78, 2527 ( 1974 ).

CH3

<9H, H2 S

Chupka, W. A., and Russell, M. E.,

ol NH^ by Photo lo ni zat 1 on, J.

( 1968 ).

NH3 , H2 0

Chupka, W. A., Russell, M. E . , and Refaey, K. , TonMolecule and Chemi - ion i zat 1 on Reactions in W

2 by

Photoionizatlon, J. Chem. Phys. 48, 1518 (1968).

Beauchamp, J. L., Ion Cyclotron Resonance Spectroscopy, Ann

.

Rev. Phys. Chem. 22, 527 (1971).

CH4 , SiH4 , AsH,, HF, He, Ne, Ar, Kr, Xe, C ? H 4 , C 3 H

6

, trans-2-C4 H

8 , cls-2-C4 HgJ 1 -C 4 HQ , iso -C4 P0

. HCHfl, CH7 CH6,

C2 H

5 CH6, (CH3

) 2 C6, CH3 6H, CgHgOH, (CH3) 2 6, (C 2 H

5

) 2

<3,

< CH2 ) 2 0 ( 1 , 2 -Epoxyethane ) , ( CH2

) 3 & ( 1 , 3 - Epoxypropan e ), CH3 SH, (CH3

) 2 S

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

Ion Cyclotron Resonance Spectroscopy for the Study of

the Intrinsic Properties and Reactivity of Transition

Metal Complexes in the Gas Phase. Ion-Molecule Reactions

of Iron Pen tacarbonyl , J. Am. Chem. Soc. 9_3, 4924

( 1971 ).

NH3 , Fe(C0)5 , Hgtf, HCl

Russell, A. S. , Fontana, C. M. , and Simons, J. H . , Low Velocity Hydrogen Ion Scattering in Hydrogen, Water

and Ammonia, J. Chem. Phys. 9, 381 (1941).

H2 , NH3

Ion-Molecule Reactions

Chem. Phys. 48, 1527

Munson, M. S. B. , Proton Affinities and the Methyl

Inductive Effect, J. Am. Chem. Soc. 87., 2332 ( 1965 ).
H

2 0, C& 3 0H, (CH3

) 2 6, HCH0, CH3CH0, (CH^jCft, HC00H,

CH3 C00H, KH3 , CH3 NH2 , (CH3> 2NH, ( CH3

> 3 N

Burt, J. A., Dunn, J. L. , McEwan, M. J., Sutton, M. M.

,

Roche, A. E., and Schiff, H. T., Some Ion- Molecule

Reactions of H3 and the Proton Affinity of H 2

, J. Chen.

Phys. 52, 6062 (1970).

H2 , 0 2 , N2 , C02

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

Patt, S. L., Thermochemica I Properties and Ion-Molecule

Reactions of the Alkyl Hal ides in the Gas Phase by Ion

Cyclotron Resonance Spectroscopy, J. Am. Chem. Soc.

94, 2798 ( 1972 )

.

C3 Hfe , C 2H

5

T, CH 3 I, H

2 S, CgHgBr, CgHgCl, H

2 6, C2 H 5

F,

CH3 Br, C

2 H4 , CH3Cl, CgH2 , CH3 F, C0, HCl

Pierce, R. C, and Porter, R. F. , Ion- Molecule Chemistry

of BF 3 and HBF2 in Hydrogen, Inorg. Chem. i*, 1087

( 1975 ).

BHF2 , BF3 , CH4 , ^2

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., 11 23 ( 1970 ).

C2 H5 0N02 , C6 H 1Q ( Cyclohexene ), CH 3N0 2

Goldenf eld, I. V., Korostyshevsky, I. Z., and Mischanchuk,

B. G. , Analysis of Field Ion Energies in a Mass Spectrometer, Int. J. Mass Spectrom. Ion Phys. 13, 297 (1974).

H2 0, H2

S, NH3

, HC00H

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 ).

CAH4N3 0C5 H9

04 (Cytidlne), C

5H3 N

4 C

5 H9

e» 4

( 9 - 0-D-Ribo -
f uranosyl puri ne ) , CgH^N^CgHgtf^ (Adenosine),

CgH^Nc;6Cg H j 3

<3 4

( 2 '

, 3' - 0- Isopropyli de ne guano si ne ) , C

4 H

3 N

2 0

2 C5 H9

f, 4 (Uridine), C

5 H5N 202 C sHg0^ (Thymidine),

C 4 H

5 N 202C5 H9

6 4

(

5

» 6 " Di

n

ydro ur 1 di ne >

» C

4 H3 N

2

fl ? C

8 H

l

64

( 2

' , 3 ' - 0 - I sopropyl ide neur idi ne ) , ^io^13N 5 ( 6 -Ami no - 9 -cyclopentylpuri ne ) , C

6 F-,Ng0 ( 8-Methylguanine ), C4 Hc N

3 0 (Cytosine), C6 H

6

N

4

( 6 - Me t hyIpur 1 ne ) , C 5 HgN 5

( 6- Ami nopurine ) , C^HK Ng 0 (Guanine), C^F^NgSg

(Dithiouracil), C

g F

4 N

4 (Purine), CgF^N^e ( Hypoxanthine ) C4 H3 N2 6H ( ? "Hydroxy 3-diazine ), C

5F

f N

2

<=, 2 (Thy1111118 )* C

4K4M

2

fl 2 (Uracil), CgF-jN^Cl ( 6 - Chloropur in e ), (CH3

) 2 NH, (CH3) 3N, NH3 , CH^NH2 X34 - 73 Long, J., and Munson, B. , Proton Affinities of Some

Oxygenated Compounds, J. Am. Chem. Soc . 95, 2427 (19 7 3),

NH3 , CH3C00CH2 CH2 CH3 , C

2 H5 C00CH3 , CH3 Ce)0C 2 H5 , CH3 C60CH 3

, (CH3

) 2 C0, CH2 "C0, HC60CF2 CH 2 CH3

, i so -C^Hp. HC00C 2 H

5

, tert-C4 H

g

6H, jLso-C^Hjg, iso-C3 H 7e(H, (CH 3

) 2 0, n-C^Hy^H,

HC00CH^, CH3CH0, CF3 C00H, CgHgOH, CH3 0H, HC00H, HjS,

CF 3 C00H, FCH0 , H

2 «, C2 H4 , CH3 Cl, (C 2 H

5

) 2 «

X35 - 68 Gray, G. A., Study of Ion-Molecule Reactions and

Reaction Mechanisms in Acetonitrile by Ton Cyclotron

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

CH3 CN, N

2

, HCN, CH^0H, CH-jCH.0, (CH 3

) 2 C0, ( C,H5 ) ? 0

X36 - 69 Searles, S. K. , Dzldi6, I., and Kebarle, P., Proton

Affinities of the Alkali Hydroxides, J. Am. Chem. Soc.

91 . 281 0 ( 1969 ).

L10H, Na0H, K0H, Cs0H

X37 - 70 Holtz, D • , Beauchamp, J. L. , and Eyler, J. R. , Acidity,

Basicity, and Ion-Molecule Reactions of Phosphlne in

the Gas Phase by Ton Cyclotron Resonance Spectroscopy,

J. Am. Chem. Soc. 92, 7045 (1970 ).

PH3 , H2 6, NH3 , C2 H4 , CH4 , CH3 CH0, (CH3

) 2 C0

X3 8 - 70 McDaniel, D . H. , Coffman, N . B • , and Strong, J. M.

,

Proton Affinity of Trlme thylphosphi ne , J. Am. Chem.

9
Soc. 92, 6697 (1970).

(C2 H5

) 3

N, (CH3

) 3 P, (Ca 3

) 3 N, (CH 3) 2 NH, NH3 , PH 3

Foster, M. S., and Beauchamp, J. L. , Gas-Phase Ion

Chemistry of Azomethane by Ion Cyclotron Resonance

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

NH.3 , CH2 N9( Dlazomethane ), tra ns-CH-,NT -NCH 3

. CHjNHg

McActoo, D. J., McLaiferty, F. W. , and Bente, P. F. , III,

Ion Cyclotron Resonance Spectroscopy in Structure

Determination. II. Propyl Tons, J. Am. Chem. Soc.

94. 2027 ( 1972 ).

C3 H6 (Cyclopropane), CH3 0H, HgS

Solomon, J. J., and Porter, R. F., Chemical Ionization

Mass Spectrometry of Selected Boron Hydrides, J. Am.

Chem. Soc. 94, 1443 ( 1 972 ).

B

2 H 6» B

4H8» B

5 H9» B5 D9» B

5 H 11» B6 H 10» C

3 H6» 1 " C4 H8» H2 S

H2 6, C

2 H4 , CH4 , C 3D

6 , C

3H 4 , (CH3

) 2

C<3

Brauman, J. I., Riveros, J. M. , and Blair, L. K.,

Gas-Phase Basicities of Amines, J . Am. Chem. Soc.

93, 391 4 ( 1 971 ).

tert -C4 Hi5 NH2. neo-CgHj jNHg, iso-C3 H? NB;

. n-C 3 H 7 NH2

, C2 H5 NH2 , CH3 NH2 , NH3 , (C2 H

5

) 2 NH, (CH3

) 2 NH, (C 2 H5

) 3 N,

(CH3

) 3 N

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

Constants for Gas-Phase Ionic Reactions. Accurate Deter

mlnation of Relative Proton Affinities, J. Am. Chem.

Soc. 93, 4314 ( 1971 ).

( CH2 ) g NH ( Plperldine ), (CH3) 3 N, ( CH2

) 4 NH (Pyrrolidine),

(CH2

) 3 NH ( Trimethylenimine )

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

and Gas -Phase Ion Chemistry of Hydrogen Fluoride,

Inorg. Chem. 1±, 1229 (1975).

10
BF, M

2 , CPt 2 , CH4 Chonp, S. L., and Fr ELnkliiij J L • , Proton Affinities

of Benzene, Toluene, and the Xylenes, J. Am. Chem. Soc

.

94 . 6630 ( 1972 ).

C

6 H6 (Benzene), C

6H5 CH 3 (Toluene), C

6H 4 (CH 3

) ?

( 1 , A-Di methylbenzene ) , CgH^f CH3 ) ?

( 1 , 2 - Di met hy Ibenz ene ), C

6 H6 (CE3

) 2( 1 , 3-Dimethylbenzene ), HCflflH, CH 3 SB, (CH 3

) ? 6,

CH3 «H, C4 B4 « (Fiiran)

Chong, S. L. , and Franklin, J. L. , Beats of Formation

of Protonated Cyclopropane, Met hylcyc lopropane, and

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

C

3 B6 , CH30H, BC0<9E, C

3 H6 (Cyclopropane), t rans -2-C 4 B

Q

. C3 B^CB3

( Methylcyclopr opane ) , CgHg

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

Basicities of Ammonia, Methylamine s, Anilines, and

Pyridine from Gas-Phase Proton-Exchange Equilibria,

J. Am. Chem. Soc. 94, 512 8 ( 1972 ).

NH3 , CE 3NH2 , (CB3

) 2 NB, ( CHj ) 3 N, C6 H5 NHCB3 (N-Methylanillne >, CgHgN ( Pyridine), CgHgUHj (Aniline)

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

Relative Gas-Phase Basicities of Alkylamines. Correlation

with Solution Basicity, J. Am. Chem. Soc. 94, 4726 (1972).

NH3 , CB3 NB2 , C2 H5 NB2 , n-C 3H 7NH2 , n-C4 H

g

NH2

, iso -C 4 B

? NBr

. i.so-C3 B7NH2 , sec-C4 B9 NH2 , tert-C^H^NH^ . ( CE3 ) 2 NH,

(C 2H

5

) 2 NH » ( G"C3 H

7

) 2 NH » (a-C4 H5> 2 NH» ( iso-C^B., > 2 NH.

(CB3

) 3 N, (C2 Hc; ) 3N, (n-C3 H 7 ) 3 N

Kriemler, P., and Buttrill, S. E., Jr., Ion-Molecule

Reactions and the Proton Affinities of the Ni troal tcane s

.

I. Nit rome thane and Nitroethane, J. Am. Chem. Soc. 9.5,

1365 ( 1 973 ).

CH3 N62 , (CH3

) 2 C6, CH3 CH0, CH3 CN, C2 B5 0E, C 2 H5CH0,

C2 H 50N02 , C3 H6 , HgS, CH3 0H, CgHgtftfg

11
Pierce, P. C, and Porter, P. F. , Low-Temperature

Chemical Ionization Mass Spectrometry of Boron Hydrides

The Proton Affinities of Diborane and Tetraborane( 10 ), J. Am. Chem. Soc. £5, 38*9 ( 1 973 ).

P2 H6* B4 H10

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

Phase Ion Equilibria Studies of the Hydrogen Ion in

Wat er -Dimethyl Ether and Me thanol - Di me thyl , J. Am. Chem

Soc. 96, 3359 ( 1 974 ).

H2 6, CH3 6H, (CH3

) 2 6

Staley, P. H., and Beauchamp, J. L. , Basicities and IonMolecule Peactions of the Met hy Iphosphines in the C?as Phase by Ion Cyclotron Resonance Spectroscopy, J. Am.

Chem. Soc. 96, 6252 ( 1974).

CH^PH2 , (CH3

) 2 PH, (CH3

) 3 P, NH3 , CH3 NH2 , trans -CH^N'NCH,

( i_so-C3 H7 ) 2

0, (C2 H5

) 2 9, iso-C 3H 7 6C 2 H

5 , CF 3 CH2 KW2

, (CH3

) 2 NH, C

2H

5NH2 , (CH3

) 3 N, (C2 H5

> 3 N, (CH 3

> 2 NC 2 H5

, (C2 H

5

) 2 NCH3

Holtz, D., Beauchamp, J. L., and Woodpate, S. D .

,

Nucleophilic Displacement Reactions in the Gas Phase,

J. Am. Chem. Soc. 92, 7484 (1970).

HCl, CH3 F, CH3 Cl, C

2 H5 Cl, H

2 0

Beauchamp, J. L. , and Caserio, M. C, Ion-Molecule Reactions

of 2-Butanol by Ion Cyclotron Resonance Spectroscopy,

J. Am. Chem. Soc. 94 . 2638 (1972).

sec-C4 H

g 6H, iso -C 3 H 76H, t ert-C^H^gH

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

CgHgO* Structural Isomers by Ion Cyclotron

Resonance Spectroscopy, J. Am. Chem. Soc. 92, 1 4"77

( 1970 ).

(CH2

> 2 6 ( 1 , 2-Epoxyethane ), CH-jCHO, CH 3 0H, (CH 3

) 2 6

12
X57 - 72 Arnett, E. M., Jones, F. M. , III* Taagepera, M. , Henrterson,

W. G. , Beauchamp, J. L., Holtz, T> • , and Taft, R. W. , A Complete Thermodynamic Analysis of the "Anomalous

tfrder" of Amine Basicities in Solution, J. Am. Chen.

Soc. 94, 4724 ( 1972 ).

NH3 , CH 3NH 2

, ( CH3 ) 2 NH, (CH3

)3 N, C2 F5 NH2 , (C2Ke) ? NH,

(C 2 H

5

) 3 N, iso-C3

R

7NR2

, te rt - C^ H^NEU . (CH2

> 3 NH

( Trimethylenimlne ), ( CHg )^NH (Pyrrolidine), ( CHg ) 5 NH

( Plperidine

)

X58 - 75 French, M. , and Kebarle, P., Pyrolysis of CgH^ and other

I on-Molecule Reactions in Methane containing Traces

of Ethane, Can. J. Chem. 53, 2268 ( 1975 ).

CH4 , C

2 H6

X59 - 75 Foster, M. S., and Beauchamp, J. L., Gas-Phase Ion Chemistry

of Iron Pen tacarbonyl 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 ).

(CH3

tf) 2 C6, Fe(C6) 5 , NH 3 , (CH3

) 2 6, HCl , HgS, HCN, CF^NH,

X60 - 75 Foster, M. S., and Beauchamp, J. L. , Ion-Molecule Reactions

and Gas-Phase Basicity of Ferrocene, J. Am. Chem. Soc.

97, 4814 ( 1975 ).

( CgH5 ) 2 Fe ( Bis( cyclopentadienyl )i ron ), Pfl 3 , NH 3 ,

( iso-C3 H7

) 2

f», trans-CH3 N-NCH3 , CH3 NH2 , HgS

X61 - 73 Cheng, T. M. H . , and Lampe , F. W. , SIHg and the Proton

Affinity of Monosilane, Chem. Phys. Letters 1_9, 532

( 1973 ).

SIH^, ^2^2

X62 - 70 Eyler, J, R., Study of Ion-Molecule Reactions In Phosphlne

by Ion Cyclotron Resonance, Inorg. Chem. 9, 981 (1970).

PH3 , CH 3CH6, ( CH3 ) 2 C6

13

\
Bli.n1:, R. J. s McMahon, T. B., and Beauchamp, J. L. , OasPhase Ion Chemistry of Fluo rome than es by Ion Cyclotron

Resonance Spectroscopy. New Techniques for the

Determination of Carbonium Ion Stabilities, J. Am. Chem.

Soc. 96, 1269 ( 1974).

C2 H2 , CH3 F, CH2 F2 , CHF 3

, C6, HCl, CH4 , CF 4 , N

g

Dzldic, I, / Relative Gas-Phase Basicities of Some Amines,

Anilines, and Pyridines. An Application of Some

Bronsted Acids as Peactants in Chemical Ionization

Mass Spectrometry, J. Am. Chem. Soc. 94_, 8333 (19*72).

C? H 13 N ( 1 -Azabicyclo[ 2. 2. 2 ]octane ), C 10 H

21 NH2 , CgHgN

(Pyridine), C

5 H4NN( CH3 ) 2

( 4- Di me tbylami nopyri d i ne ), C

6H5N(CH3

) 2( N,N-Dimethylaniline), ( CH 3 )gNH,

C

6H5NPCH3

( N-Methylani line ), CgH^( NH2

) 0

( 1 , 3-Diaminobenzene ), ( C

fe H5 )^N ( Triphe nylami ne ) , CH3NH2 , C

6 H 4(NH2

) 2( 1 , 2 -Diami nobenzen e ) , C

6 H4 (NH2

) 2

( 1 , 4 -Di ami nobenzene ), ( C

& H5 ) 2NH ( Diphenylamine ),

C

6 H5 MH2 (Aniline), NH3

Taagepera, M., Henderson, W. G. , Brownlee, R. T . C,

Beauchamp, J. L., Foltz, D. , and Taft, R. W.

,

Gas-Phase Basicities and Pyridine Substituent

Effects, J. Am. Chem. Soc. 94, 1369 (1972).

C5 H4 N6CH3( 4-Methoxypyridine ), C

5H 4NCE^

( 4-Methylpyridine ), C

5 Hg N (Pyridine), C

5 H4 NCF3

( 4-Trlf luoromethylpyridlne ), C

5 H4NN1 2

( 4 - N i tropyri d i ne )

,

( CH3 ) 2 NH

Aue, 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_,

A136 ( 1975).

NH3

, ( C 2 H5 ) 3 N, CyHj-gN ( 1 - Az afolcyclo[ 2 . 2 . 2 ] oct ane ) ,

( n -C-jH-, ) 3N , Cj QHj ( 1 - Azabicyclo[ 3 . 3 . 3 ]undecane ), CH3 NH2

Bowers, M. T., and Elleman, D. D . , 6n the Relative Proton

Affinity of Argon and Deuterium, J. Am. Chem. Soc.

Ik
92 . 7258 ( 1970 )

.

, Ar

Yamdagni, R., and Kebarle, P., Gas-Phase Basicities of

Amines. Hydrogen Bonding in Proton-Bound Amine Diroers

and Proton - Induced Cyclization of a,u-Diamines, J. Am.

Chem. Soc. 95, 3504 ( 1973 ).

CR3 C0NH2 , C 4 H5 N (Pyrrole), C.gH^NHg (Aniline),

C

6H 4

( NH 2 )0CH3 ( 2-Methoxyaniline ), CgH^NHCgH^

(N-Ethylanillne ), C

6 H

5 N(CH^) 2

( N, N- Dimet hy lani li ne ) , C6 H

5

N( CH3 )C 2 H5 (N-Ethyl-N-methylaniline ), (CH 2

) 5

Nff

( Piperidine ), C

6 H5

N(

C

2 Hg

) 2

( N, N- Di et hy lani line ), NH2 CH2CH2 NR2 , NH2

( CH2

) 3 NF2

, NH2 ( CH2 ) 3 CH( NH 2 )CH 3

, NH2 ( CH2 ) 5CH( NH2 )CH3

Beggs, D. P., and Lampe, F. W. , Si Hg Formation in Ionized

Si lane -Methane Mixtures, J. Chem. Phys. 49, 4230 ( 1968).

SiH4

Henderson, W. G., Taagepera, M., Foltz, D. , Mc I ve r, R. T. , Jr.

Beauchamp, J. L., and Taft, R. W. , Methyl Substituent

Effects in Protonated Aliphatic Amines and Their

Radical Cations, J. Am. Chem. Soc. 94_, 4728 ( 1972).

NH3 , CH3 NH2 , (CH3

) 2NH, ( CH3 > 3 N, CgH^NHg, i so-C-,H7NH2. tert.-C4 H

9NH2

Holtz, D., Beauchamp, J. L. , Henderson, W. G. , and Taft,

R. W. , Basicity of Nitrogen Trifluoride in the Gas

Phase by Ion Cyclotron Resonance, Inorg. Chem. 10 . 201 ( 1971 ).

NF 3 , HCl, CH4

Betowski, L. D. , Solomon, J. J., and Porter, R. F., The

Proton Affinity of Borazlne, Inorg. Chem. 1 1

.

424

( 1972 ).

B 3H 6N 3 * Borazlne ) , PH3 , CHg-C-CHg, CH3 C*CCH3 , NH 3

15
Hodges, R. V., and Beauchamp, J. L. , Basicity and Ion-Molecule

Reactions of Trimethylarsine in the Gas Phase Determined

by Ion Cyclotron Resonance Spectroscopy, Inorg. Chen.

14, 2887 ( 1975 ).

(CH3

) 3 As, NH3> CH 3 NH2 , CF 3 (CH 2 )^NH 2

Moran, T. F. , and Hamill, W. H. , Cross Sections of IonPermanent -Dipole Reactions by Mass Spectrometry,

J. Chem. Phys. 39, 1M3 ( 1963 ).

HCN, CH3 CN, C2 H5 CN, n-C3 H 7CN, n-C 4 H

g

CN

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

of Methyl Thio- and I sothiocyana te , Int. J. Mass Spectrom.

Ion Phys. j_5, 303 ( 1974).

CH^SCN, CE3 NCS

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. 9_5, 2669 ( 1973).

NH2 CH2 CH2 NH2 , n-C3 H7NH 2J NTH 2( CH 2 ) 3 NH 2 , n-C^gKHg,

NH2 ( CH2 ) 4 NH2 , n-C 5 Hxl NH2

, ( CH2 ) gNH 2

, n-C6Hj 3 KH2, NH2 ( CH2 ) 6 NH2, n-C7H1(; NH?J CH3 <3CH2 CH2 NH 2 , C 4H9 N0

( Morpholine ), ( CH 2 ) gNH ( Piper idine ), C4H 1Q N2 (Piperazine)

Solka, B. H. , and Harrison, A. G., Bitnolecular Peactions of

Trapped Ions. Part XI. Rates and Equilibria in Proton*

Transfer Reactions of CF^SHg, Int. J. Mass Spectrom.

Ion Phys. .17, 379 ( 1975 ).

CH3 SH, CH3CH0, C

2 H5 CH0, ( CH 3 ) 2 0

Schiff, H. I., and Bohme, D. K. , Flowing afterglow Studies

at York University, Int. J. Mass Spectrom. Ion Phys.

16, 167 ( 1975 ).

C0, N2 0, CH4 , C02 , N2 , H2 , 0g , Ar, Xe , N0

Gorden, R. , Jr., and Sieck, L. W., Ion-Molecule Reactions in

Isopropanol: Implications for its Radiolysis, J. Res.

16
NBS 76A, 655 (1972).

SF 6

X80 - 74 Hehre, W. J., Mclver, R. T. , Jr., Pople, J. A., and Schleyer,

P. v. P., Alkyl Substituent Effects on -the Stability of

Protonated Benzene, J. Am. Chem. Soc . 5_6_, 7162 (19^4).

CgHcCH3 (Toluene), CgHgCgHg ( Ethylbenzene ) , C 6 H

5C3 H 7

( Propylbenzene ), C^K^C^j ( Isopropylbenzen e ), C

6 H5C 4 H 9 ( Butyl benzene ) , Cg H^C^ Hq ( tert -Butylbenzene ). HC66CH3

X8 1 - 75 Vogt , J., and Beauchamp, J. L. , Reactions of CHFg with n-Donor

Bases by Ion Cyclotron Resonance Spectroscopy. The

Proton Affinity of D i f luo roca rb ene , J. Am. Chem. Soc.

92. 6682 ( 1975 ).

CF2 , CH3 CN, CH3 CE6, CH3

tfH, AsH 3

, HCHQ, HCN, H

2

«=t

X82 - 71 Hellner, L., and Sieck, L. W. , Kinetic Mass Spe ct rometr ic

Investigation of the Reactions of t-C^Hg Ions with

Some Simple Polar Molecules at Thermal Energies,

J. Res. NBS 75A. 487 ( 1971 ).

(CH3

) 2C6, iso-C4 H 0 . lso-C 3 H ? 0H, NH3 , CH 2 *C0

X83 - 59 Lampe, F. W. , and Field, F. H. , Reaction of Gaseous Ions.

VII. Methane-Hydrogen and the Proton Affinities of

Methane and Ethane, J. Am. Chem. Soc. 8_1, 3242 ( 1959 ).

CH4» C2 H6

X84 - 75 Hlraoka, K., and Kebarle, P., Information on the Proton

Affinity and Protolysis of Propane from Measurement

of the Ion Cluster Equilibrium: CgH^ CH^ - C

3 H*,

Can. J. Chem. 53. 970 ( 1975).

C3H8» C2 H6

X85 - 73 Isolani, P. C. , Riveros, J. M. , and Tledemann, P. W. , Gas

Phase Proton Affinities of Carbonyl Compounds by Ion

Cyclotron Resonance Spectroscopy, J. Chem. Soc. Faraday

17
Trans. II 69, 102 3 ( 1973).

HC60H, CH3 0H, C^HgfH, HC00CH3 , CH3 C09H, HC00C2 H5 , CH3 C00CH3 , CH3 C06C2 H5 , (CH^,)2 C0, C^H^CflCH^ , (

C

2 F

5

) ? C0,

CH3 C0SC2 H^, CH3 C00CH2 CH2CH3 , CH3C0SCH 2 CH2 CH 3

, (n-C4 Ho) 2 6,

(n-C4 H9

) 2 S, CIC06C2 H

5

X86 - 71 Porter, R. F., and Solomon, J. J., Chemical Ionization Mass

Spectrometry of Borazine, J. Am. Chem. Soc . 93, 56

( 1971 ).

B 3 H6

N 3

< Borazine >

X87 - 74 Foster, M. S., Williamson, A. D. , /ind Beauchamp, J. L.,

Photo i oni za ti on Mass Spectrometry of trans -Azome thane . Int. J. Mass Spectrom. Ion Phys. 1_5, 429 ( 1974).

trans -CH3 N-NCH3 , CHFgCHgNHg, NH3

X88 - 75 Payzant, J. D. , Schiff, H. I., a net Bohme, D. K. , Determination

of the Proton Affinity from the Kinetics of Proton

Transfer Reactions. V. The Equilibrium H* Kr * KrH*

H2 and the Relative Proton Affinity of Kr and H

2

, J. Chem. Phys. 63, 149 (1975).

H

2

, Kr

X89 - 73 Bohme, D. K. , Fennelly, P., Hemsworth, R. S., and Schiff, H.

I., Preferred Direction of Proton Transfer Between

CgHy and C0, CH& , N

20, and C 2 H4 at 300 *K, J. Am. Chem.

Soc. 95, 7512 (1973).

C2 H6

, C0, CH4 , N2 0, C

2 H4

X90 - 68 Brauman, J. I., and Blair, L. K. , Gas-Phase Acidities of

Alcohols. Effects of Alkyl Groups, J. Am. Chem. Soc.

90 . 6561 ( 1968 ).

(CH3

) 3 N, (CH3) 2 NH, CH3 NH2 , NH3

X91 - 71 Field, F. H. , and Beggs, 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).

18
°3 Ha

X92 - 64 Hunson, M. S. B. , Franklin, J. L., and Field, F. H. , High

Pressure Mass Spec trome tr ic Study of Alkanes, J. Phys.

Chem. 68, 3098 ( 1964).

C2 H6» C 3H8

X93 - 7 4 Vfyatt, 1? . H. , Holtz, D . , McMahon, T. B. , and Beauchamp, J.

L., Acidity, Basicity, and Ion-Molecule Reactions of

Arsine in the Gas Phase by Ion Cyclotron Resonance

Spectroscopy, Inorg. Chem. 1.3, 151 1 ( 1974 ).

AsH3 , PH^, H2

S, CH3CH«CH2 , CH 3 6H, CH 3 Cl

X94 - 75 Kim, J. K. , Theard, L. P., and Huntress, W. T., Jr., Proton

Transfer Reactions from H3 Ions to N2

, 02

, and C0

Molecules, Chem. Phys. Letters 32, 610 (1975).

0

2 , H2

X95 - 74 Eemsworth, R. S. , Payzant, J. D. , Schiff, H. I., and Bohme,

D. K . , Rate Constants at 297*K for Proton Transfer

Reactions with NH3 Comparisons with Classical Theories

and Exothermic ity, Chem. Phys. Letters 26 . 417 (1974).

H2 , CH4 , C6, N2 . C

2 H6 , N

2 3

X96 - 72 Kasper, S. F., and Franklin, J. L. , Ion-Molecule Reactions

in the System C62 -CH, J. Chem. Phys. 56 . 1156 (1972),

C62 , CH4

X97 - 65 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).

Er, Xe, 62

, N0, Hg0, CH^

X98 - 72 Blair, A. S. , and Harrison, A. G., Blmolecular Reactions of

Trapped Ions. V. Ionic Chemistry of Simple Oxygen-containing Molecules, Can. J. Chem. 51 , 703 ( 1972 ).

19
(CH 3

) 2 6, (CH3

) 2 C6, CH3 CHfl, (CD3) 2

tf, ( CH2 ) 2

fl (1,2-Epoxy

e -thane )

Taft, R. W. , Taagepera, M. , Summerhays , K. D., and Mitsky, J.,

Regarding Heats of Solution of Gaseous Anilinium and

Pyridinium Ions in Water and Intrinsic Basicities in

Aqueous Solution, J. Am. Chera. Soc . 95, 3811 ( 1973 ).

(CR2

) 2 NH ( Ethylenimine ), (CHg^NCH-j ( N-Me thyl pyrrol idine ) , C6 H5 NH2 (Aniline), C& Hj jNHj ( Amlnocyclohex ane ) (CH3

) 2 NH, C

5 H5 N ( Pyridine),

Dixon, D. A., Holtz, D. , and Beauchamp, J. L., Acidity,

Basicity, and Gas-Phase Ion Chemistry of Hydrogen

Selenide by Ion Cyclotron Resonance Spectroscopy, Inorg.

Chem. li, 960 ( 1972).

H2 Se, AsH3 , H2 S, HCN, Hgtf

Jelus, B. L. , Murray, R. K. , Jr., and Munson, B., Studies in

Chemical Ionization Mass Spectrometry. Secondary Alcohols

with Isobutane, J. Am. Chem. Soc. 97, 2362 (1975).

C^HjqO ( Cyclohexanone

)

Dzidl6, I., and McCloskey, J. A., Chemical Ionization Mass

Spectrometry Using Ammonia Reagent Gas. Selective

Protonation of Conjugated Ketones, 6rg. Mass Spectrom.

6, 939 ( 1972 ).

( Cfe H

5 CH"CH

)

2 C0 ( 1 , 5-Di phe nyl-1 ,4-pentadien-3-one ), C

5 K2 62 (CH3

) 2( 2,6-Dimethyl-4-pyrone ), C 27H 44fl

( 4-Cholesten-3-one ), C ?7 H44 0 ( 5 - Choi est en- 3- one ), NH

Kebarle, P., Haynes, R. N. , and Collins, J. G. , Competitive

Solvation of the Hydrogen Ion by Water and Methanol

Molecules Studied in the Gas Phase, J. Am. Chem. Soc.

89, 5753 ( 1967 ).

H2 0, CH3 6H

Stevenson, D. P., and Schissler, D. fl. , Rate of the Gaseous

Reactions, X* YH - XH* Y, J. Chem. Phys. 23, 1353

20
( 1955 ).

Kr, CH4

XI 05 - 43 Simons, J. H., Francis, H. T. , Muschlitz, E. E . , Jr., and

Fryburg, G. C. , The Scattering of Loir Velocity Hydrogen

Ions in Water Vapor, J. Chem. Phys. 11 . 316 (1943).

H2 6

X106 - 75 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).

C

g

H5 N (Pyridine), (CH 2

) 5NH ( Piperidine ), ( CH

g ) 2 NH

( Ethylenimine ), (CH3

> 2 NH, CH-jCH-NTCjHg, (C 2 H

5

> 2 NH,

(CH 3

) 3N, (CH2) 3 NH ( Trimethylenimine ), ( CH2 ) 2 NCH3

( N-Methylethylenimine ), CjHgNHj, CHjMHj , C ^HgN

( 1 -Azabicyclo[ 1 . 1 . 0 }butane ), CH 3CN, CgH^CN, CH 36H,

(CH 2

) 26 ( 1 ,2-Epoxyethane), (CH-,) 2 6, (CgH,.)^, (CF2

) 3 6

( 1 , 3 -Epoxypropane ), (CH3

) 2C6, HgQ

X107 - 74 Staley, R. H., and Beaucharap, J. L., Relationship of Nitrogen

Lone Pair Interactions to Thermodynamic Parameters

Associated with Amine Basicities, J. Am. Chem. Soc.

96 . 1604 ( 1974 ).

(CH3

) 3

N, (C2 H5

) 3 N, C? H

13 N ( 1 - Azabicyc lo[ 2. 2. 2 ]octane ), CgHjgNg ( 1 , 4-Diazabicyc lo[ 2 . 2. 2 ]oc tane ), NH3

XI 08 - 65 Waddington, T. C. , Lattice Energies of Phosphonium Bromide

and Iodide and the Proton Affinity of Phosphlne, Trans.

Faraday Soc. 61 . 2652 (1965).

PH3

XI 09 - 55 Wendlandt, W., Proton Affinity of Phosphine in the Phosphonium

Halides, Science 122 . 831 (1955).

PH3

XI 10 • 71 GoodUffe, A. L., Jenkins, H * D. B. , Martin, S. V., and

21
Waddington, T. C. , The Proton Affinity of Gaseous

Ammonia, the Charge Distribution on the NH^ Ion and the

Lattice Energies of NH4 Cl, NH^Br, and NH4

I , Mol. Phys.

21., 761 ( 1971 ).

NH 3

Sherman, J., Crystal Energies of Ionic Compounds and

Thermoc hemi cal Applications, Chem. Pev. j 1 . 93 ( 1932 ).

NH3 , H

2

<3

Bleick, W. E . , The Lattice Energies of the Ammonium Halides

r and the Proton Affinity of Ammonia, J. Chem. Phys. 2,

160 ( 1934 ).

NH3

Kondratlev, V. N. , and SokoloV, N. D. , On the Heat of

Hydration of Ions, Zh. Fiz. Knim. 29, 1265 ( 1955 ).

H

2 0, CH3 0H, C,H56F, n-C4 Hg 0H

Vetchinkin, S« T., Psherichnov, 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, 1 269 ( 1959 ).

NH,

Altshuller, A. P., Thermodynamic Properties of the Ammonium

Ion, J. Am. Chem. Soc. 77, 34-80 (1955).

NH 3

Lias, S. G., and AusLoos, P., Ion-Molecule Reactions. Their

Role in Radiation Chemistry (American Chemical Society,

Washington, D. C. , 1975) p. 91.

C2 H6» C3H8 , C4 F 1Q

Van Raalte, 13., and Harrison, A. G. , Energetics and

22
Mechanism of Hydronium Ton Formation by Electron

Impact, Can. J. Chem. 4_L, 3118 (1963).

F2 6

Munson, M. S. B., and Franklin, J. L. , Energetics of Some

Gaseous Oxygenated Organic Ions, J. Phys. Chen. 63 . 3191 ( 1964 ).

H2

fl, CH3 6H, HCO0H, CH-jCOOH, C2 Hc C00H

Hobrock, B. G. , and Klser, R. W. , Electron Impact Spectroscopy

of Sulfur Compounds. I. 2 -Thlabutane, 2 -Th iapentane,

and 2, 3 -Di thlabutane, J. Phys. Chem. 66, 1648 (1962).

S , CH-^ SH

Hobrock, B. G. , and Klser, R. W., Electron Impact Investigations of Sulfur Compounds. II. 3 - Met hy I- 2 - Thlabutane,

4-Thia- 1 -Pentene, and 3 ,4 - Dlthl ahexane, J. Phys. Chem.

67, 648 ( 1963 ).

H2 S, CH3 SH

Haney, M. A., and Franklin, J. L. , Heats of Formation of

H^6 , H^S , and NH^ by Electron Impact, J. Chem. Phys.

50, 2028 ( 1969 )

.

H2 0, H

2

S, NH3

Franklin, J. L., Lampe, F. W., and Lumpkin, F. E. , The

Proton Affinity of Benzene, J. Am. Chem. Soc.

81 . 3152 ( 1959 ).

CgHg ( Benzene

)

Haney, M. A., and Franklin, J. L., Excess Energies in Mass

Spectra of some Oxygen- cont ain ing Organic Compounds,

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

( CH2) 2 0 ( 1 , 2-Epoxyethane

)

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

23
Formation of Some Oxygenated Ions and the Proton

Affinities of Carbonyl Compounds, Can. J. Chem. 44,

1625 (1966).

HCH0 , CH3CH6, CgHgCHfl, FC00H, CH-gCeflH, C

? H cCfl0H

Harrison, A. G . , and Keyes, F. G . , Structure of the C ? H

5 0*

Ton in the Mass Spectra of 2-Alkanols, J. Am. Chem. Soc

90, 5046 ( 1 968 ) .

CH3CH0

Godbole, E. W. , and Kebarle, P., Ionization and Dissociation

of Deuterated Ethyl and Isopropyl Acetates and Ethyl

Formate under Electron Impact, Trans. Faraday Soc. 58,

1 897 ( 1962 )

.

CH3 C06H

Wada, Y. , and Kiser, R. W. , A Mass Spectrometric Study of

Some Alky 1 - Substi tuted Phosphines, J. Phys. Chem. 68 . 2290 ( 1 964 ).

PH3

Hayhurst, A. N. , and Telford, N. R. , Proton Affinity of Wate

and the Mechanism and Kinetics of Production of H

3

fl in

Flames of Hg, ^2* ano- **2 » Chem. Soc. Faraday Trans.

I 71, 1 352 ( 1975 )*.

H2 0

Staley, R. H., and Beauchamp, J. L., Intrinsic Acid-Base

Properties of Molecules. Binding Energies of Li to

ir- and n-Donor Bases, J. Am. Chem. Soc. 97 . 5920

(1975 ).

(CH3

) 3N, C5 H5 N (Pyridine), HC0N(CH 3

) 2 , NH3 , (CH3

) 2 S,

CH3 C00CH3 , (CH3

) 2 C0, iso-C^Hg, (CH 3

) 2 ©, RC00CH3 , CH 3CN,

CH3 CH0, C6 Hfe (Benzene), CH 3 0H, C3 H

& , CH3 N0g, iso -C 3 H7

I . i_so-C3 H7Br, HCH0, HCN, iso-C3 H7 Cl . is_o-C 3 H ? F, CH3 C*CH,

H2 0, C2 H5

F, CH3 Cl, CH3 F, CHgFg, C 6Hj 2

( Cyc lohexane

)

24
Q2 - 74 Jen, J. S. , and Thomas, T. D. , Core Ionization Potentials

in Dimethyl Ether and Methyl Amine, J. Flectron

Spectrosc. 4, 43 (1974).

N 2 H4

03 - 75 Colonna, F. P., Dlstefano, G., Pignataro, S. , Pitacco, G . , and "Valentin, E., Ionization Energies of Some Amines

and Enamines and an Estimation of Their Relative

Basicity in Gaseous Phase, J. Chem. Soc. Faraday

Trans. IT 71, 1572 ( 1975).

C4 H9 N6 (Morpholine ), ( CH,, ) gNH ( Pi pe rl di ne ) , ( CH2

) 4 NH

(Pyrrolidine), C^HgNflCgHg ( N-( 1 - Cyclohexenyl )mort>holine ), (CH2

) 5 NC6 H9 (N-( 1 -Cyclohexenyl )pi perl dine ) , (CH 2

) 4MC 6F 9

( N-( 1 -Cyclohexenyl pyrrolidine ), C^gNSCgHj j ( N -Cyclohexylmorpholine ), ( CH2 ) 5 NC6 H

T 1

( N-Cyclohexylpiperidlne ), ( CHg ) 4 KC6 H 1 j

( N-Cyclohexylpyrrolidlne ), C4 HqN0C 4H7

(N-(2-Methyl-l -propenyl korphol lne ),

( CH2 ) 5 NC4 H7

( N-( 2-Methyl-l -propenyl )piperidine ),

( CH2

) 4 NC4 Hy

( N-( 2 -Methyl - 1 - propenyl )pyrrol idine ), C4 HgN6C4 H9 (N-Isobutylmorphollne, (CH 2

) 5NC 4H

g

( N-I sob ut yl pipe ri dine ), ( CH2 ) 4NC4HC

(N-I sob utyl pyrrol idine

)

04 - 75 Carroll, T. X., Smith, S. R . , and Thomas, T. D. , Correlation

between Proton Affinity and Core-Electron Ionization

Potentials for Double - Bonded Oxygen. Site of Protonation

in Esters, J. Am. Chem. Soc. 97, 659 ( 1975).

HCH0, HC00H, CH3CH0, (CH3

) 2

<9, CH3 C00CH3

, ( CH3

) 2 C0

05 - 74 Martin, R. L . , and Shirley, D. A., The Relation of Core-Level

Binding Energy Shifts to Proton Affinity and Lewis

Basicity, J. Am. Chem. Soc. 96, 5299 ( 1974 ).

NH3 , CH3NH2 , (CH3

) 2 NH, (CH3)3 N

06 - 74 Bel'skll, V. E., and Izmallov, R. I., Proton Affinity of

Atoms and Ions, Zh. 0bshch. Khim. 44, 2297 ( 1974 ).

H, He, Li, Be, B, C, N, 0, F, Na, Mg, Al, Si, P, S, Cl

,

25
Nl , Zn, Br, Kr, I, Hg

Futrell, J. H. , and Tiernan, T. 0., Ion-Molecule Reactions,

in: Fundamental Processes in Radiation Chemistry, ed.

P. Ausloos ( W il ey- Tntersc ienc e , New York, 1968) Chap. 4.

Futrell, J. H. , Ion Cyclotron Resonance Mass Spectroscooy,

in: Dynamic Mass Spectrometry, Vol. 2, edt. D. Price

( Heyden, New York, 1971 ) Chap. 3.

Stevenson, D. P., Ion-Molecule Reactions in: Mass Spectrometry

ed. C. A. McDowell (McGraw-Hill, New York, 1963) Chap. 13

Beauchamp, J. L., Ion CycloAron Resonance Spectroscopy, Ann.

T?ev. Phys. Chem. 22, 527 ( 1971 ).

Lampe, F. W. , Franklin, J. L. , and Field, F. H. , Kinetics

of the Reactions of Ions with Molecules, in: Progress

in Reaction Kinetics, Vol. 1, ed. G. Porter and B.

Stevens ( Pergamon, New York, 1961 ) Chap. 3.

Mc Daniel, E. W. , Cermak, V., Dalgarno, A., Ferguson, E. E.,

and Friedman, L. , Ion-Molecule Reactions ( Wi le y- In ter

science, New York, 1970 ).

Lias, S. G., and Ausloos, P., Ion-Molecule Reactions. Their

Role in Radiation Chemistry (American Chemical Society,

Washington, D. C. , 1975 ).

Ferguson, E. E., Ion-Molecule Reactions, Ann. Rev. Phys. Chem.

26, 1 7 ( 1975 ).

Bowers, M. T. , and Su, T. , Thermal Ion-Molecule Reactions,

Adv. Electron. Electron Phys. 34, 223 ( 1973 ).

Arnett, E. M., Gas-Phase Proton Transfer - a Breakthrough

for Solution Chemistry, Acc . Chem. Res. 6, 404 ( 1973 ).

Friedman, L. , and Reuben, B. G. , A Review of Ion-Molecule

Reactions, Adv. Chem. Phys. 1_9, 33 ( 1971 ).

Kebarle, P., Ions and Ion- Solvent Molecule Interactions in

the Gas Phase, in: Ions and Ion Pairs in Organic

26
Reactions, Vol. 1, ed. M. Szwarc ( Wiley- Interscience,

New York, 1972) Chap. 2.

Rl 3 - 59 Lampe, F. W. , and Field, F. H. , Reactions of Ions with

Molecules in the Gas Phase, Tetrahedron 7, 189 ( 1959).

Rl 4 - 62 Talrose, V. L. , Ion Molecule Reactions in Gases, Pure Appl

.

Chera. 5, 455 (1962).

Rl 5 - 75 Ausloos, P., ed. , Interaction between Ions and Molecules,

NAT6 Advanced Study Institutes Series (Plenum, New York,

1975 ).

Rl 6 - 60 Purup, J., Les Reactions Entre Ions Positifs and Molecules

En Phase Gaseuse. Application a la Chi mi e des Rayonnement

s

( Gauthier-Villars, Paris, 1960 ).

Rl 7 - 72 Franklin, J. L., ed. , Ion Molecule Reactions, Vols. 1 and 2 (Plenum, New York, 1972).

Rl 8 - 66 Ausloos, P. J., ed. , Ion-Molecule Reactions in the Gas Phase,

Advances in Chemistry Series, Vol. 58 (American Chemical

Society, Washington, D. C, 1966).

R19 - 73 Bell, R. P., The Proton in Chemistry (Cornell University Press,

Ithaca, N. Y . , 1973).

27
Molecule Index

H2 X6-71, Xll-58, X13-72, X14-73, X17-7 3j X23-68,

X26-41, X28- 7 0 1 X30-75, XS8-75, X94-75,

X95-74

^2 XI 3-7 2, X14-73, X15-68, X6^-70

He X24-71, 06-74

Li 06-74

Be Q6-74

B 06-74

B 2 H6 X41-72, X50-73

B 4 Hg X41-72

B 4 H 1Q X50-73

B

5 H9 X41-72

B

5D9 X41-72

BgHjj X41-72

B

6 H 1Q X41-72

06-74

CH4 X6-71, X7-73, X8-71, X9-65, X10-57, Xll-58,

X12-69, X24-71, X30-75, X37-76, X41-72,

X44-75, X58-75, X63-74, X71-71, X78-75,

X83-59, X89-73, X95-74, X96-72, X97-65,

X104-55

28
C2 H2 X29-72, X61-73, X63- 7 4

C2 H4 X3-70, X5-69, Xll-58, X16-75, X18-68, X24-71,

X29-72, X34-73, X37-"'0, X41-72, X89-73

C 2 H

6 X9-65, Xll-58, X46-72, X58-75, X83-59, X84-75,

X89-73, X92-64, X95-74, X116-75

CH 2 -C-CH 2 X41-72, X72-72

CH3C*CH 01-75

C 3 H6 X3-70, Xll-58, X24-71, X29-72, X*l-72, X46-72,

X49-73, X93-74, 01-75

C 3D6 X41 -72

C3 H6

( Cyclopropane

)

X46-72

C 3 H8 Xll-58, X84-75, X91-71, X92-64, X116-75

CH3C «CCH3 X72-72

1 -C4H 8 X24-71, X41-72

cls -2-C4H Q X3-70, X24-71

trans -2 -C^Hg X24-71, X46-72

is_o-C AHg X24-71, X34-73, X82-71, Ol -75

C3 H5CH3

( Methylcyc lopropane

)

X46-72

C4 H 10 X116-75

lso-C 5H 10 X34-73

C6 H6

( Benzene ) X12-69, X45-72, Y6-59, 01-75

29
C6 H 10

(Cyclohexene ) X31 -70

C

6 H12

(Cyclohexane) 01-75

C6 H5 CH3

( Toluene

)

X45-72, X80-74

C6 H5C 2 H5

( Ethylbenzene

)

X80-74

C 6 H4 (CH3 ) 2

( 1, 2 -Di met hylbenz ene

)

X45-72

^6^4^ ^2

( 1,3 -Dime thylbe nzene ) X45-72

C6 H4 (CH3 ) 2

( 1 ,4-Dimethylbenzene

)

X45-72

C6 H5 C 3 H7

{ Propylbenzene

)

X80-74

C6 H5C 3 H7

( Isopropylbenzene

)

X80-74

C6 H5 C4 H9

( Butylbenzene

)

X80-74

C6 H5 C4 H9

( tert -Butylbenzene ) X80-74

06-74

X6-71, X28-70, X35-68, X44-75, X63-74, X78-75,

X95-74

NH- X5-69, X12-69, X22-68, X25-71, X26-41,

X27-65, X32-74, X33-^5, X34-73, X37-70,

X38-70, X39-72, X42- 7 1, X4^-72, X48-72,

X52-74, X57-72, X59-75, X60-75, X64-72,

X66-75, X70-72, X 72 - 7 2 , X73-75, X82-71,

30
X87-74, X90-68, X102-72, X107-74, X110-71,

Xlll-32, X112-34, X114-59, X115-55, Y5-69,

01-75, 05-74

N

2 H4 C2-74

B

3 H6N3

( Borazine ) X72-^2, X86-^l

HCN X12-69, X35-68, X59-75, X74-63, X81-75,

X100-72, 01-75

CH 3NH2 X12-69, X27-65, X33-75, X39-72, XA2-71,

X47-72, X48-72, X52-74, X57-72, X59-75,

X60-75, X64-72, X66-75, X70-72, X73-75,

X90-68, X106-75, 05-74

CH-,CN X12-69, X35-68, X49- _7 3, X74-63, X81 -75

X106-75, 01-75

( CH2 ) 2 NH

( F + hylenimine ) X99-73, X106-75

C 2 H5NH2 X42-71, X48-72, X52-74, X57-72, X70-72, X106-75

(CH3 ) 2 NH X27-65, X33-75, X38-70, X42-71, X4?-72, X48- _'2,

X52-74, X57-72, X64-^2, X65-72, X70-72, X90-68,

X99-73, XI 06-75, 05-74

C2 H5CN X74-63, X106-75

C

3 H5 N

( 1 -Azablcyclo[ 1 .1 .0]bu-tane ) X106-75

( CH2 ) 2 NCH3

( N-Methylethylenimine ) X106-75

( CH2

) 3 NH

( Trimethylenlmine ) X43-71, X57-72, X106-75

a-c3H 7NH 2 X42-71, X48-72, X76-73

iso-C 3H7 NH2 X42-71, X48-72, X57-72

31
(CH3

) 3N X27-65, X33-75, X38-70, X42-7], X43-71, X^^-~'2 S X48-72, X52-74, X57-72, X70-72, X90-68,

XlOe-^S, X107-74, 01-75, 05-74

C 4 H5 N

( Pyrrole

)

X68-73

a -C 3H 7CN X74-63

CH3CH-NC 2 H5 X106-75

( CH2) 4 NH

( Pyrrol id ine

)

X43-71, X57-72, 03-75

X48-72, X76-73

sec-C4 H^NH2 X48-72

iso -C 4 H

? NH2 X48-"7 2

ter_t-C4 H9 KH2 X42-71, X48-72, X57-72, X70-72

( C

2 H5 ) 2 NH X42-71, X48-72, X57-72, X106-75

(CH3

) 2NC 2H

5 X52-74

C

5 H5N

( Pyridine

)

X47-72, X64-72, X65-72, X99-73, XI 06-75, Ol -75

a-c4H9CN X74-63

( CH2

) 4 NCF3

( N-Methylpyrrolldine

)

X99 -73

( CH2) 5 NH

( Piperidine) X43-71, X57-72, X68-73, X76-73, X106-75, 03-75

j J NH 2 X76-73

X42-71

(C 2H5

) 2NCH3 X52-74

32
C 5 H4 NCH3

( 4-Methylpyridlne

)

X65 -7 2

C

6 H5NH2

( Anil ine

)

X47-72, X64-72, X68-73, X99-73

C6 H 1

1

NH2

( Aminocyc lohexa ne ) XS9 -73

a-c6H 13KH 2 X76-73

( n-C3 H7

) 2 NH X48-72

( iso -C3 H7) 2NH X48-72

( C

2H5 ) 3 N X38-70, X42-71, X48-72, X52-74, X57-72,

X66-75, X107-74

C 6 H5 NHCH3

( N-Methylanlline

)

X47-72, X64-72

C7 H 13 N

( 1 -Azabicyclo[2 .2.2 ]octane ) X64-72, X66-75, X107-74

u-c7h 15 nh2 X76-7 3

C

6 H

5 NHC2 H5

( N-Ethylaniline ) X63-73

C6H5N(CH3

) 2

( N.N-Dimethylanlline) X64-72, X68-73

(CH2

) 4NC4 H7

(N-( 2 -Methyl -1 -pro penyl ) pyrrol 1 dine ) 03-75

(CH2

) ANC4H9

( N-Isobutylpyrrolidlne ) 03-75

(n-C4HQ ) 2 NH X48-72

C6 H5N(CH3 )C2 H5

( N -Ethyl -N -me thylani line ) X68-73

33
( CH2 ) 5 NC4 R7

( N -( 2 -Methyl-1 -propenyl )piperidlne ) 03-75

( CH2

) 5 NC4 H9

( N'Isobutylpiperldine ) 03-75

(n-C3 H?

) 3 N X48-72, X66-75

C

6 E5 N(C2 H5

) 2 (N.N-Dlethylanillne) X68-73

(CH2

) 4 NC 6 H9

( N -( 1 -Cyclohexenyl )pyrroli dine ) 03-75

(CH2

) 4 NC6 H„

( N-Cyclohexyl pyrrolidine ) 03-75

C

10H19 N

( 1 -Azabic yclo[ 3.3.3 ]undecane ) X66 -7 5

D.-C 10 H 21 NH 2 X64-72

(CH2

) 5 NC6 H9

(N-( 1 -Cyclohexenyl )piperldlne ) 03-75

(CH2

) 5 NC6 H n

( N -Cyc lohexylpi peridine ) 03-75

(C6H5

) 2 NH

( Diphenylatnine ) X64-72

(C 6H5

) 3 N

( Triphenylamine ) X64-72

CH 2N2

( Dia zonae thane ) X39-7 2

trans -CHgN-NCH-, X39-72, X52-74, X60-75, X87-74

NH2CH2CH2 NH2 X68-73, X76-73

NH 2(CH2

) 3 NH2 X68-73, X76-73

34
C 4 H 10 N

2 (Piperazine) X76-73

NH2(CH2

) 4 NH2 X76-73

KR 2(CH2

) 5 NH 2 X76-73

NH2(CH2

) 3 CH( NH2)CH-, X68-73

C

6 H4( NH2

) 2

( 1 , 2 -D iam inob enzene ) X64-72

C6 H4( NH2 ) 2

( 1 ,3-Diaminobenzene ) X64-72

C6 H4( NH2 ) 2

( 1 , 4 -D iam i nob enzene ) X6&-72

C6 H 12 N2

( 1 ,4-Diazabicyclo[2.2.2 ]oc+ane ) X10 7-74

NH 2(CH2

) 6NH 2 X76-73

C

5 H4 NN( CH3 ) 2 (4-Dimethylaminopypictlne ) X64-72

NH2 ( CH2 ) 5 CH( NH2 )CH3 X68-7 3

C

5 H3 N4CH3

( 6 -Me -thyI purine ) X33-75

C5 H5 N5

( 6 -Amlnopuri ne ) X33-75

C l

0

H 1

3

N5

( 6 -Amino -9 -cycl opentyl purine ) X33-7 5

0 06-74

62 X6-71, X17-73, X28-70, X78-75, X94-75, X97-65

H

2 6 Xl-72, X2-73, X3-70, X4-69, X5-69, Xll-58,

X12-69, X16-75, X18-68, X20-73, X22-68, X25-71,

35
X27-65, X29-72, X32-74, X34-73, X37-70, X41-72,

X51-74, X54-70, X59-7S, X81-75, X97-65,

X100-72, X103-67, X105-43, X106-75, Xlll-32,

Yl-63, Y2-64, Y5-69, Ol - 75

D

2

e> X2-73, X4-69

C6 X6-71, X7-73, X12-69, X18-6B, X29-72, X63-^4,

X^S-^S. X89- _'3, X95-74

ce. X6-71, X7-73, X28-70, X44-75, X78-75, X96-72

N6 X6-71, X78-75, X97-65

N2 6 X6-71, X7-73, X78-75, X89-73, X95-74

Li 0H X36-69

HCH6 X3-70, X12-69, X16-75, X24-71, X27-65, X34-73,

X81-75, Y8-66, 01-75, 04-^5

CH 30H X3-70, Xll-58, X12-69, X16-75, X21-7A, X24-71,

X27-65, X34-73, X35-68, X40-72, X45-72,

X46-72, X49-73, X51-74, X56-70, X81-75,

X85-73, X93-74, X103-67, X106-75, XI 13-55,

Y2-64, 01-75

CH2

-Cf« X34-73, X82-71

CH 3CH0 X5-69, X12-6S, X24-71, X27-65, X34-73, X35-68,

X37-70, X49-73, X56-70, X62-70, X^7-75,

X81-75, X98-72, Y8-66. Y9-66, 01-75, 04-75

(CH2 ) 2

f»

( 1

, 2-Epoxyethane

)

X24-71, X56-70, X98-72, X106-75, Y7-69

C2 H5 6F Xll-58, X18-68, X24-71, X34-73, X49-73,

X113-55, Y8-66

(CH3 ) 2 0 X12-69, X24-71, X27-65, X34-73, X45-72, X51

74

X56-70, X59-75, X77-75, X98-72, X106-75,

01-75, 04-75

36
( CD 3

) 2 6

C2 H5CH6

X98-72

X24-71, X77-75, X85-73, Y8-66

( CH3) 2 C0 X3-70, X5-69, X12-69, X24-71, X27-65, X3*-

X35-68, X37-70, X41-72, X49-73, X62-70,

X82-71, X85-73, X98-72, X106-75, 01-75, O*

(CH2 ) 3 0

( 1

, 3-Epoxyprooan e

)

X24-71, X106-75

H-C3 H7 6H X34 -73

is*>-C 3 H70H X34-73, X55-72, X82-71

C4 H4 0

( Furan

)

X45-72

C2 HgC0CH3 X85-73

n-C4H96H XI 1 3-55

sec -C^H^OH X55-72

teri-C4H9 0H X34-73, X55-72

(c 2H5

) 2 e X24-71, X34-73, X35-68, X52-74, X106-75

(C 2H5 ) 2C0 X85-73

iso-C3H70C2 H5 X52-74

C6 H 10 G

( Cyclohexanone

)

X101 -75

( i so -C3H-, ) 20 X52-74, X60-75

( n-C4 H9

) 2 0 X85-73

(

C

6H5CH-CH) 2 C0

( 1 ,5-Diphenyl -1 , 4 -pentadl en-3 -one ) X102-72

37
C27H4 46

( A -Cholesten-3 - one ) XI 0? -72

C 27H*4 0

( 5 -C ho I es t en - 3 - o n e ) X102-72

HC06H Xl-^2, X12-69, X27-65, X32-74, X34-73,

X45-72, X46-72, X85-73, Y2-64, Y8-66, 04-75

CH3 C66H X27-65, X34-73, X85-73, Y2-64, Y8-66, Y10-62

HC00CF- X34-73, X80-74, X85-73, 01-75

C O HCC(30H Y2-64, Y8-66

HC00C 2 H

5 X34-73, X85-73

CH3C00CH3 X34-73, X85-73, 01-75, 04-75

HceecH2 cH2CH 3 X34-73

CH3C06C 2 H

5 X34-73, X85-73

C2 H

5C60CH 3 X34-73

CH3 C06CH2 CH2 CH3 X34-73, X85-73

C

5 H

262 (CH 3

) 2

( 2, 6-Diroethyl -4 -pyrone ) X102-72

( CH3 0 ) 2 C0 X59 -75

CH3C0NH 2 X68-7 3

HC0N( CH3

) 2 01-75

CH36CF2 CH2 NH2 X76-73

c4 H9

Ne*

( Morphol ine

)

X76-73, 03-75

C 5 HA N0CH3

C 4 *Methoxypyr idlne

)

X65-72

38
C6 H4( NH2 )6CH3

( 2 -Methoxyanili ne

)

X68-73

C 4 H8 N*C4 H7

( N -( 2-Methyl-l -propenyl )morpholine ) 03-7 5

C4 H8 N6C4 H9

( N-Isobutylmorpholine

)

03-75

C 4 H

8N6C6 H9

( N -( 1 -Cyc lohe xe nyl )morphol in e ) 03-75

C 4 H

Q N6C6 H 11

( N-Cyclohexylmorpholine ) 03-75

C 4 H3N 2 6H

( 2 -Hydro xy-1 ,3-dlazi ne ) X33-75

c4 h5n 36

( Cytosine

)

X33-75

c5 h4 n4 6

( Hypoxant nine

)

X33-75

C5 H5 N5 6

( Guan ine

)

X33-75

c6 h7n5 o

( 8-Methylguanine

)

X33-75

CH3 N62 X31-70, X49-73, 01-75

C

2 H5 N62 X49 -7 3

C 4 H4N2 6

2

( Urac il ) X33-75

C 5H4 NN62

( 4-Nitropyridlne

)

X65-72

C5 H6 N2 6 2

( Thymine

)

X33-75

39
C

2 H5

0N<3 2 X31-70, X49-73

C5 H3N4C5 H9

04

( <3 -/9-D-Pibofuranosyl purine ) X33-75

c 5H4N5c5 H9 ed

(Adenosine) X33-75

C 5H5 N 202 C 5H9 63

(Thymidine) X33-75

C4 HAN3 6C5 H964

(Cyiridine) X33-75

C 5H4N56C 8H13 04

( 2 *

a 3' -0 -T so propyl idenegua nosine) X33-75

C4 H3N 2 0

2C 5 H9 6 4

(Uridine) X33-75

C 4 H5N2 0 2 C 5 Hg 04

( 5, 6-Dihydrourldlne ) X33-^5

C4 H3 N 2 62 C 8 H13 04

( 2',3'-6-Isopropylldeneurldlne ) X33-75

06-74

HF X24-71, X44-75

BF 3 X30-75

CF 2 X81-75

CF 4 X6-71, X 63-74

NF 3 X71-71

BHF2 X30-75

CH3F X29-72, X54-70, X63-74, Ol -75

C2 H3F X16-75

1+0
C

2 H5F X16-75, X29-72, 01-75

iaa-c3 H7

F 01-75

CH2F

2 X63-74, 01 -75

CH 2 -CF 2 X16-75

cis-CHF'CHF X16-75

trans-CHF "CHF X 1 6-^5

CHF3 X63-74

C

2 HF 3 X16-75

CHF 2CH2 NH2 Xe^-74

CF 3CH2 NH2 X52-74

CF 3( CH2

) 3 NH2 X73-^5

C 5 H4 NCF 3

( 4 -Trlfluoromethylpyrldine ) X65-72

CF 3 C66H X34-73

Ne X24-71

Na 06-74

Na6H X36-69

Mg 06-74

Al 06-74

Si 06-74

S1H4 X24-71, X61-73, X69-68

P 06-74

Hi
PH 3 X5-69, X12-69, X37-^o, X38-70, X60-^5, X62-70,

X72-72, X93-74, X108-65, X109-55, Yll-6*

CH3PH2 X52-74

(CH3

) 2 PF X52-74

(CH3

) 3 P X38-70, X52-74

S 06-74

H2 S Xl-72, X12-69, X16-75, X18-68, X19-58, X20^73,

X21-74, X29-72, X32-74, X34-73, X40-72, X41 -72,

X49-73, X60-75, X93-74, X100-74, Y3-62, Y4-63,

r Y5-69

D

2 S Xl-72

SF 6 X7S-7 2

CH3SH X12-69, X24-71, X45-72. X77-75, Y3-62, Y4-63

(CH3

) 2 S X24-71, 01-75

<a~C4 H9> 2 S X85-73

CH3 SCN X75-74

CH3NCS X75-74

CH3C6SC2 H5 X85-73

CH3C0SCH2 CH2CH3 X85-^3

CI 06-74

HCl X12-69, X19-58, X25-71, X29-72, X54-70,

X59-75, X63-74, X71-71

CH3Cl X12-69. X29-72, X34-73, X54-70, X93-74, 01-75

CD3Cl X16-75

1+2
C

2 H5C1

iaa-c3 H7ci

C5 H3 N4Cl

( 6 -Chloropurine

)

CIC06C 2H 5

Ar

K6H

(C 5H 5

) 2Fe

(Bis( cyclopentadienyl )iron

)

Fe<ce ) 5

Ni

Zn

AsH3

( CH3) 3As

HgSe

Br

HBr

CH 3Br

C 2 H5Br

iso -C-jH-.Br

Kr

I

HI

X29-72, X54-70

01 -75

X33-75

X85-73

X6-71, X24-71, X67-70, X78-75

X36-69

X60-75

X25-71, X59-75

06-74

06-74

X24-71, X81-75, X93-74, X100-72

X73-75

X100-72

06-74

X12-69

X29-72

X29-72

01-75

X24-71, X88-75, X97-65, X104-55, 06-74

06-74

X12-69
CH3

I X29-72

C 2 H5I X16-75, X29-^2

isp-C^H-,1 01-75

Xe X24-71, X78-75, X97-65

CsQH X36-69

Hg 06-74

1*4
Au-thor Index

Al"tshuller, A. P.

Arne-t-t, E. M.

Aue, D. H.

Ausloos, P.

Beauchamp, J* L.

Beggs, D. P.

Bell, P. P.

BeVskil, V. E. Bente, P. F . , III

Berkowltz, J.

Betowskl, L. K.

Blair, A. S.

Blair, L. K.

Bleick, W. E.

Blint, P. J.

Bohme, D . K.

Bone, L. I.

Bowers, II. T.

Brauman, J . I

Br lees, J. P.

Brown lee, P. T. C.

Burt, J. A.

But-trill, S. E. , Jr.

Carroll, T. X.

Caserio, M. S.

Cermak, V.

Cheng, T. M. H. Chong, S. L.

Chupka, W. A.

Co ffoan , N. B.

Collins, J. G.

X115-55

X57-72, R10-73

X43-71, X48-72, X66-75, X76-73, X106-75

X116-75, P7-75, R15-75

X5-69, X18-68, X24-71, X25-"M, X29-72, X37-70,

X39-72, X44-71, X52-74, X54-^0, X55-72, X56-70,

X57-72, X59-75. X60-75, X63-74, X65-72, X70-72,

X71-71, X73-75, X81-75, X87-74, X93-74, X100-72,

X107-74, 01-^5, R4-^l

X69-68, X91-71

R19-73

06-74

X40-72

X8-71

X72-72

X98-73

X42-71, X90-68

XI 12-34

X63-74

X6-71, X7-73, X17-73, X78-75, X88-75, XS9-^3 3 X95-74

X20-73, X21-74

X43-71, X48-72, X66-75, X67-70, X76-73,

X106-75, R9-73

X42-71, X90-68

X47-72

X65-72

X28-70

X18-68, X31-70, X49-73

04-75

X55-72

R6-70

X61 -73

Xl-72, X45-72, X46-72

X8-71, X22-68, X23-68

X38-70

X103-67
Colonna, F. P. Cotter, R. J.

Crowley, M. G.

Dalgarno, A.

DePaz, M.

Distefano, G.

Dixon, D. A. Dunbar, R. C.

Dunkln, D. B.

Dunn, J. L.

Durup, J.

Dzidi6, I.

03-^5

X2-73, X13-72

X14-73

R6-70

X4-69

03-75

X100-7?

X56-70

X7-73

X28- 7 0

R16-60

X36-69, X64-72, X102-72

Ell em an , D . D

.

Eyler, J. P.

X67-70

X37-70, X62-70

Fehsenfeld,, F. C.

Fennelly, P. F. Ferguson, E. E.

Field, F. H.

Fontana, C. *f, Foster, M. S.

Francis, H. T.

Frankevitch, E. L

F r a nk lin, J. L.

French, M.

Friedman, L.

Fryburg, G. C.

Futrell, J. H.

X7-73

X17-73, X89-73-

R6-70, R8-75

X9-65, X10-57, X19-58, X83-5<=, X91-71, X92-64,

X97-65, R5-61, R13-59

X26-41

X25-71, X39-72, X44-71, X59-75, X60-75, X87-74

XI 05-43

XI 1 -58

Xl-72, X12-69, X45-72, X46-72, X92-64, X96-72,

Y2-64, Y5-69, Y6-59, Y7- 69 ," R5- 6 1 . R17-72

X58-75

X4-69, X15-68, R6-70, Rll-71

XI 05-43

Pl-68, R2-71

Godbole, E . W.

Goldenfeld, I . V. Goodliffe, A. L.

Gorden, R., Jr.

Gould, R. F.

Gray, G. A.

Grimsrud, E. P.

Grossheim, T. R.

Y10-62

X32-74

XI 10-71

X79-72

R 18-66

X35-68

X51 -74

X14-73

Hamill, W. H. X74-63

1+6
Haney, M. A.

Harris, H. H.

Harrison, A. G.

Hayhurst, A. N.

Haynes, R. N.

Hehre, W. J.

Hellner, L.

Hemsworth, R. S.

Henderson, W. G.

Hiraoka, K.

Hobrock, B. G.

Hodges, R. V.

Holtz, D.

Hopkins, J. M.

Huntress, W. T. , Jr.

Isolani, P. C.

Ivko, A.

Izmailov, R. I.

Jelus, B. L.

Jen, J. S.

Jenkins, H. D. B.

Jones, F. M. , III

Kasper, S. F.

Kebarle, P.

Keyes, B. G.

Kim, J K . Kiser, R. W. Kondratiev, V. N.

Eoroa tyshevsky, I, Z.

Koski, W. S. Kr iemler, P.

Lampe, F. W.

Leventhal, J, J.

Lias, S. G.

Long, J.

Lumpkin, H. E.

X12-69, Y5-69, Y7-69

X14-73

X">7-75, X98-73, Yl-63, Y8-66, Y9-68

Zl -75

X103-67

X80-74

X82-71

X7-73, X17-73, X89-73, 95-7*

X57-72, X65-72, X?0-^2, X71-71

X51-74, X84-75

Y3-62, Y4-63

X73-^5

X5-69, X29-72, X37-70, X54-70, X57-7?, X65-72,

X70-72, X71-71, X93-74, X100-72

X20-73

X94-75

X85-69

Y8-66

06-74

X101-75

02-74

XI 1 0-71

X57 -7 2

X96-72

X36-69, X47-72, X51-74, X58-75, X68-73, X84-75,

X103-67, Y10-62, R12-72

Y9-68

X94-75

Y3-62, Y4-63, Yll-64

XI 13-55

X32-74

X2-73, X13-72

X31-70, X49-73

X10-57, X19-58, X61-73, X69-68, X83-59, Y6-59,

R5-61, R13-59

X4-69, X14-73, X15-68

X116-75, R7-75

X3-70, X34-73

Y6-59

•1+7
Martin, R. L.

Martin, S. V.

McActoo, D. J.

McAllister, T.

McCloskey, J. A.

McBanlel, D. H. McDaniel, E. 'W. McEwan, M. J.

Mclver, R. T., Jr.

McLaflerty, F. W.

McMahon, T. B.

Mlschanchuk, B. G.

Mitsky, J.

Moran, T. F.

Muneon, M. S. B.

Murray, R. K., Jr.

Muse hlitz, E. E . , Jr,

Myers, R. A., Jr.

Patt, S. L.

Payzant, J. D.

Pierce, R. C.

Pignataro, S.

Pitacco, G.

Pople, J. A.

Porter, R. F.

Pshenichnov, E. A.

05-74

XI 10-71

X40-72

X75-74

X33-75, X102-72

X38-70

56-70

X28-70

X70-72, X80-74

X40-72

X63-74, X93-74

X32-74

X99-73

X74-6 3

X3-70, X9-65, X27-65, X34-^3 # X92-64, X9?-65,

X101-75, Y2-64

X101 -75

X105-43

XI -72

X29-72

X88-75, X95-74

X30-75, X50-73

03-75

03-75

X80-74

X30-75, X41-72, X50-73, X72-72, X86-71

XI 14-59

Refaey, K.

Reuben, B. G.

Ridge, D. P.

Rlveros, J. M.

Roche, A. E.

Rozett, R. W.

Rundle, H. W.

Russell, A. S.

Russell, M. E.

X23-68

Rl 1 -71

X16-75

X42-71, X85-69

X6-71, X28-70

X13-72

X7-73

X26-41

X22-68, X23-68

Schiff, H. I.

Schissler, D. 6.

Schleyer, P. v. R,

X6-71, X7-73, X17-73, X28-70, X78-75, X88-75,

X89-73, X95-74

X104-55

X80-74

U8
Searles, S. K.

Sherman, J.

Shirley, D. A.

Sleek, L. W.

Simons, J. H.

Smith, S. P. Sokolov, N. D.

Solka, B. H. Solomon, J. J.

Staley, P. H.

Stevenson, D. P.

Strong, J. M.

Su, T.

Summerhays, K. D< Sutton, M. M.

Taagepera, M.

Taft, R. W.

Tal'Pose, V. L. Theard, L. P.

Thomas, T. D.

Tiedemann, P. W.

Tiernan, T. 0.

X36-69

XI 1 1 - 32

05-74

X79-72, X82-71

X26-41, X105-43

04-75

X113-55, X114-59

X77-75

X41-72, X72-72, X86-71

X52-74, X107-74, 01-75

X104-55, R3-63

X38-70

R9-73

X99-73

X6-71, X28-70

X57-72, X65-72, X70-72, X99-73

X57-72, X65-72, X70-72, X71-71, X99-

Xll-58, R14-52

X94-75

02-74, 04-75

X85-69

Rl -68

Valentin, E,

Van Raalte, D.

Vetchinkin, S. T Vogt, J.

03-75

Yl-63, Y8-66

XI 14-59

X81-75

Wada, Y.

Waddlngton, T.

Webb, H. M.

Wei, L. Y.

Wendlandt, W,

Williamson, A.

Wilson, M. S.

Woessner, P. J,

Woodgate, S. D. Wyatt, R. H.

Yl 1 -64

X108-65, XI 1 0-7

l

X43-71, X48-72, X66-75, X76-73, X106

X21 -74

XI 09-55

X87-74

X33-75

X14-73

X29-72, X54-70

X93-74

Yamdagni, R, X47-72, X68-73

^9
5

i
NBS-114A (REV. 7-73)

U.S. DEPT. OF COMM. BIBLIOGRAPHIC DATA

SHEET

1. PUBLICATION OR REPORT NO. NBSIR 76-1061

2. Gov't Accession

No.

3. Recipient's Accession No.

4. TITLE AND SUBTITLE

An Annotated Bibliography on Proton Affinities

5. Publication Date Jul V 1976

6. Performing Organization Code

7. AUTHOR(S)

Kwi Hartman, Sharon Lias, Pierre Ausloos, and Henry Rosenstock

8. Performing Organ. Report No.

9. PERFORMING ORGANIZATION NAME AND ADDRESS

NATIONAL BUREAU OF STANDARDS

DEPARTMENT OF COMMERCE

WASHINGTON, D.C. 20234

10. Project/Task/Work Unit No. 3162420

11. Contract/Grant No.

12. Sponsoring Organization Name and Complete Address (Street, City, State, ZIP)

National Institute of Health

Bethesda, Maryland 20014

13. Type of Report & Period CoveredFinal

14. Sponsoring Agency Code

15. SUPPLEMENTARY NOTES

16. ABSTRACT (A 200-word or less [actual summary ol most significant information. If document includes a significant

bibliography or literature survey, mention it here.)

This bibliography consists of approximately 150 references about proton affinities

which covers the period from 1932 through 1975. This includes experimental

determinations of proton affinities in the gas phase (through observation of

proton transfer reactions, ion-molecule equilibria, and appearance potential

measurements) as well as determinations from crystal lattice energies and other

miscellaneous techniques. Also included are reviews concerned with or related

to proton affinity determinations.

17. KEY WORDS (six to twelve entries; alphabetical order; capitalize only the first letter of the first key word unless a proper name; separated by semicolons)

Basicity; bibliography, appearance potential; heat of formation; ion-molecule

equilibrium; proton affinity; proton transfer

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