RShowcasing benchtop NMR of small organic molecules
Example:Ethyl crotonate
Ethyl crotonate
Example of benchtop NMR on small organic molecules

Showcasing benchtop NMR of small organic molecules
Ethyl crotonate(C6H10ItOis2)soluble
is a colourless
Example:
Ethyl
Ethyl crotonate (C6H10OO
incrotonate
water, liquid
and is atused as2) is a colourless liquid at room temperature.
roomfortemperature.
It isIt soluble
water,and is usedasa solvent for cellulose esters as well as a plasticizer
acrylic resins.
is knowninfor
its pungent
odour.

H3C

O

CH3
H3C

a solvent for cellulose esters as well as a plasticizer
for acrylic
resins. It is known
for its pungent
Ethyl crotonate(C6H10O2odour.
) is a colourless liquid at
O
O

CH3

room temperature. It is soluble in water, and is used asa solvent for cellulose esters as well as a plasticizer
for acrylic resins. It is known for its pungent odour.

1H NMR spectrum

The 1H NMR spectrum of 25% ethyl crotonate in CDCl3 is shown in Figure 1. The spectrum was recorded

in a single scan,taking 7 seconds to acquire. All peaks and 1H-11H couplings are well resolved, and can be
1H NMR spectrum of 25% ethyl crotonate in CDClH
NMR spectrum
The
3 (v/v) is shown in Figure 1. The
assigned to the molecular structure.

spectrum was recorded in a single1scan, taking 7 seconds to acquire. All peaks and 1H-1H
The H NMR spectrum of 25% ethyl crotonate in CDCl3 (v/v) is shown in Figure 1. The
couplings are well resolved, andcan be assigned to the molecular structure.
1
1

spectrum was recorded in a single scan, taking 7 seconds to acquire. All peaks and H- H
couplings are well resolved, and can be assigned to the molecular structure.

Figure 1: Proton NMR spectrum of 25% ethyl crotonate in CDCl3.
Figure1: Proton
NMRNMR
spectrumof 25%of
ethyl
crotonatein CDCl3. in CDCl .
Figure1: Proton
spectrum
25%
ethyl crotonate
3

1H NMR RELAXATION

1H NMR relaxation
The relaxation time measurements are shown in Figures 2 - 4. Note that the relaxation
times are longest for the CH protons and shortest for the CH protons. The amplitude of the

3
1H NMR
first datarelaxation
point scales with the number of protons for the corresponding peak.

The measurements
relaxation time measurements
are shown in Figures 2 - 4. Note that the relaxation
The relaxation timeare
5.2 s for the CH3 protons.
2.7 s
3.9 s
areNotelongestthat
for the
The amplitude3.0
of stheshown in Figurestimes
2 - 4.
theCH protons and shortest
2.5 s
3.1
2.6 s
3.3peak.
s
first data point scales with the number
ofs protons
forthecorresponding
1H NMR
relaxation
relaxation times are longest for the
2.9 s
5.1 s
CH protons and shortest for the CH3
The relaxation time measurements areshown
in Figures
2and- 4.T Notethatthe relaxation(left)(right)relaxation
time
for
each
proton position of the molecule
Figure2:
ProtonT
protons. The amplitude of the first data
1
2
protons. The amplitude of thetimes arelongestfor the CH protons and shortest for the CH
3
3.0
s
5.2
s
s for each proton
3.9 s Proton T1 (left) and T2 (right) relaxation 2.7
time
point scales withfirst
thedatanumberof protons
point scaleswith the number of protons
for the corresponding peak.
2.5 smolecule.
3.1 s
2.6 s
3.3
s
positionofthefor the corresponding peak.
2.9 s
5.1 s
3.0
s
5.2
s
2.7 molecules
3.9sFigure 2: Proton T1 (left) and T2 (right) relaxation time for each proton position of the
2.5
s
3.1 s
2.6 s
3.3 s
5.1 s

2.9 s

Figure 2: Proton T1 (left) and T2 (right) relaxation time for each proton position of the molecule

Figure 3: Proton T1 relaxation time measurement of 25% ethyl crotonate in CDCl3.

Figure 3: Proton T1 relaxation time measurement of 25% ethyl crotonate in CDCl3.

Figure 2: Proton T1 relaxation time measurement of 25% ethyl crotonate in CDCl3.
Figure 3: Proton T1 relaxation time measurement of 25% ethyl crotonate in CDCl3.
Figure 4: Proton T2 relaxation time measurement of 25% ethyl crotonate in CDCl3.

Figure 4: Proton T2 relaxation time measurement of 25% ethyl crotonate in CDCl3.

Figure 4: Proton T2 relaxation time measurement of 25% ethyl crotonate in CDCl3.

Figure 3: Proton T2 relaxation time measurement of 25% ethyl crotonate in CDCl3.

2D COSY

2D COSY

The 2D COSY spectrum is shown in Figure 4. It clearly shows two spin systems (1,2) an(6,7,8). For example, the methyl group at position 1 only couples to the ethylene group aposition 2, whilst the methyl group at position 8 couples to the two CH groups at positio
6 and 7. There is no coupling of positions (6,7,8) to either 1 or 2.

2D COSY

The 2D COSY spectrum
is shown
in Figure
4. Itin Figure 4. It clearly shows two spin systems (1,2) and
The 2D COSY
spectrumis shown
clearly shows two (6,7,8).
spin systems(1,2)theand(6,7,8).
For example,
methylgroup at position 1 only couples to the ethylene group at
For example, the methyl
position
1 onlyposition group2, whilstatthe
methyl groupat position 8 couples to the two CH groups at positions
6
and
7.
There
is
no
couplingofpositionscouples to the ethylene group at position 2, whilst (6,7,8) to either 1 or 2.
the methyl group at position 8 couples to the
two CH groups at positions 6 and 7. There is no
coupling of positions (6,7,8) to either 1 or 2.

Figure 4: COSY spectrum of 25% ethyl crotonate in CDCl3. The cross-peaks andcorresponding exchanging protons are marked by colour-coded ellipses and arrows.

Figure 4: COSY spectrum of 25% ethyl crotonate in CDCl3. The cross-peaks andFigure 4: COSY spectrum of 25%
ethyl crotonate
in CDCl3protons. The cross-peaks
corresponding
exchanging
are markedandby corresponding
colour-coded ellipses and arrows.
exchanging protons are marked by colour-coded ellipses and arrows.

2D HOMONUCLEAR J-RESOLVED
SPECTROSCOPY
2D homonuclear
j-resolved spectroscopy
In the 2D homonuclear j-resolved spectrum the chemical shift is along the direct (f2)direction and the effects of proton-proton coupling along the indirect (f1) dimension. This
allows the full assignment of chemical shifts of overlapping multiplets, and can allow
different
peaks,toitbeismeasured.
possible
toprojection
extract along
information
In the 2D homonuclear j-resolved spectrum theotherwise unresolved
couplings
The
the f1 dimension
yields a “decoupled”
1D
protonspectrum.
Figure5 shows
the 2Dother.
homonuclear j-resolved
about
which
peaks
are
coupledtoeachchemical shift is along thedirect(f2)
direction
2D homonuclear j-resolved
spectroscopy
spectrum of ethyl
along
with
thetriplet
1D proton
spectrumas blue
For crotonate,example,boththeat 1.06ppm
andline. The verticaland the effects of proton-proton coupling along
projection
shows
how
the
multipletscollapse
into a single peak, which greatly simplifies
In the 2D homonuclear j-resolved spectrum
the chemical
shift
is
along
the
direct(f2)
the quartet at 3.96 ppm have a splitting of 7.10
the indirect (f1) dimension. This allows the fullthe 1D spectrum.
direction and the effects of proton-proton coupling along the indirect (f1) dimension. Thissuggesting
that
these
groupstoassignment ofchemical
shifts of overlapping
VerticaltracesHz,
throughthe peaks
2D spectrum
yieldarethecoupledpeak multiplicities,
as shown
allowsthe full assignmentof chemical shiftsof overlapping
multiplets,
and incantheallow
eachin other.
Theof thethemeasurement
coupling frequency
by the The
greenprojection
lines
Figure5,andenablesof proton-proton coupling
multiplets, andcan allow
otherwiseotherwise
unresolved
couplingsunresolved
to be measured.
along thef1 sizedimension
frequencies.
By
comparingthe coupling
frequencies
different
peaks, it is possible
a “decoupled”
1D projection
proton spectrum.
Figure 5 shows
the 2D homonuclear
j-resolved
providesinformation
about
thebetween
coupling
strength.
couplings to yields
be measured.
The
along
extract
information
about
which
peaks
are coupled to each other. For example, both thespectrum of ethyl crotonate, along with theto1D
protonspectrum
as
blue
line.
The
verticalFor example, the splitting of 1.53 Hz is due to thethe f1 dimension yields a “decoupled” 1D proton
tripletppm
andwhichthe quartet
3.96 ppm have a splitting of 7.10 Hz, suggesting thatprojection shows how the multiplets collapse
intoata1.06
singlepeak,greatlyatsimplifies
long
range
betweenpositionsand 8. provides
All
spectrum. Figure
shows the 2D homonuclear
these groups arecoupledto couplingeach other. The
size of thecoupling 6
frequency
the 1D5spectrum.
these
couplings
confirmthefindings
of
the
COSY
j-resolved spectrum
ofethyl
crotonate,
along
with
information
about
the
coupling
strength.
For
example,thesplitting
of
1.53
Hz
is due to the
Vertical traces through the peaks in the 2D spectrum yield the peak multiplicities, as shown
long
range
coupling
betweenpositions
6
and
8.
by
the
green
lines
in
Figure5,andenablesthemeasurementof
proton-proton
coupling
experiment in Figure 4.
the 1D proton spectrum as blue line. The verticalfrequencies. By comparing the coupling frequencies
between different
peaks,
it is possible
confirm thefindingsof the COSY experiment in Figure 4.
projection shows
how the multiplets collapseAll these couplings
to extract information about which peaks are coupled to each other. For example, both theinto a single triplet
peak,atwhich
greatly
theppm
1Dhave a splitting of 7.10 Hz, suggesting that
1.06 ppm
and thesimplifies
quartet at 3.96
spectrum. Verticaltracesthrough
the
peaks
in
theof the coupling frequency provides
these groups are coupled to each other. The size
information
about
the
coupling
strength.
For
example, the splitting of 1.53 Hz is due to the2D spectrum yield the peak multiplicities, as shown
long range coupling between positions 6 and 8.
by the green lines in Figure 5, and enables the
All these couplings confirm the findings of the COSY experiment in Figure 4.

7.10 Hz1.53 Hz6.65 Hz1.53 Hz7.10 Hz7.10 Hz1.53 Hz15.53 Hz6.65 Hz6.65 Hz7.10 Hz1.53 Hz15.53 Hz6.65 Hz15.53 Hz15.53 Hzeasurement of proton-proton coupling frequencies.
By comparing the coupling frequencies between

Figure 5: Homonuclear j-resolved spectrum of 25% ethyl crotonate in CDCl3. The
multiplet splitting frequencies for different couplings are colour-coded as in Figure 4.

Figure 5: Homonuclear j-resolved spectrum of 25% ethyl crotonate in CDCl3. The
multiplet splitting frequencies for different couplings are colour-coded as in Figure 4.

Figure 5: Homonuclear j-resolved spectrum of 25% ethyl crotonate in CDCl3. The
multiplet splitting frequencies for different couplings are colour-coded as in Figure 4.

2D HOMONUCLEAR J-RESOLVED SPECTROSCOPY
2D homonuclear j-resolved spectroscopy

2D homonuclear j-resolved spectroscopy

One unusual and often neglected feature of this experiment is that second order coupling
extra peaks and coupling partners are
One unusual and often neglected feature of thiseffects showThese
up in the indirect (f1) direction as extra peaks equidistant from the coupling
markedanddimension.
arrows inexperiment is that second order coupling effects
partners well removed byfromcolour-coded
the zero frequencyellipses
in the indirect
These peaks areOneunusualandoften
neglected
featureof
thisexperimentisthat
secondorder
coupling
often
neglected
asartefacts,but
providedirectevidenceofsecondorder
Figure 6. Note that this spectrum is based
oncoupling partners.
show up in the indirect (f1) direction as extra
effects show up in the indirect (f1) direction
as extrapeaks
fromarethe
coupling
These
extra peaks
andequidistantcoupling partners
markedby colour-coded ellipses and arrows in
the samedata as Figure
5, only
the scaling has
peaks equidistant from the coupling partners wellFigure in
6. Notethat this spectrum
is basedon thesame aredata as Figure 5, only the scaling has
partners well removed from the zero frequency
the indirect
dimension.
These
peaks
changed.
removed often
from neglected
the zero frequency
in the indirectchanged.
as artefacts, but provide direct
evidence of second order coupling partners.
dimension.
These
peaks
are
often
neglected
as
These extra peaks and coupling partners are marked by colour-coded ellipses and arrows inartefacts,Figure
but provide
evidence
6. Notedirectthat thisspectrumofissecond
based on the same data as Figure 5, only the scaling hasorder coupling
partners.
changed.

Figure 6: Homonuclear j-resolved spectrum of 25% ethyl crotonate in CDCl3 showing theextra peaks due to strong couplings.

Figure 6: Homonuclear j-resolved spectrum of 25% ethyl crotonate in CDCl3 showing the
FigureHomonuclear
j-resolved spectrum of 25% ethyl crotonate in CDCl3 showing
extra
peaks6:dueto strong couplings.
the extra peaks due to strong couplings.

1D 13C spectra

1D 13C SPECTRA 1D 13C spectra

The 13C NMR spectra of 25% ethyl crotonate in CDCl3 (v/v) are shown in Figure 7. The
1DCarbon experiment is sensitive to all 13C nuclei in the sample. It clearly resolves 6
13
as well
as a weaksolvent
tripletinbetween
70The
and 80 ppm.
The C NMR spectra of 25%resonances,ethyl crotonate
in CDClare shown
Figure 7.
3 (v/v)
13C DEPT experiment uses polarisation transfer between proton and carbon nuclei an
The
1DCarbonexperimentissensitive
to
all
13C
nucleiinthesample.
It
clearly
resolves
6
13
signals of CH, CH2 and CH3 groups, but the CH2
The C NMR spectra of 25% ethyl crotonate
canbe usedfor between
spectralediting.
Only
directly
to protons are visible inresonances,well as7.a The
weak1DCarbon
solvent
triplet70 appearand 80ppm.
groups
as carbons
negativepeaksattachedin the DEPT-135.
in CDCl3 areshown inasFigure
13
theseexperiments.
Sincebetween
at for167theppm
doesatnot
the DEPT spectra it mustTheC DEPTto
experimentuses
polarisationtransfer
protonandcarbonnucleiandinwhich
This
isthe
thepeakcase
peak
60showppm,
experimentis sensitive
all 13C nuclei
inthebelongtothequaternarycarbonat
position
2.
The
DEPT-90experiment
can
be
used
for
spectralediting.
Onlycarbons
directlyattached
toprotonsarevisibleinmust therefore belong to the carbon at position 2.gives only signal
sample. It clearly resolves 6 resonances, as well as
of80CH
whilst
DEPT-45
andthree
DEPT-135
give
signalsof possible
CH, CH2 and CH3 grou
these experiments.
Since
atgroups,
167 ppmdoes
notshow in thethe
DEPT
spectrait mustBythe
combining
DEPT
spectra,it isa weak solvent
triplet between
70theandpeak
ppm.
but
the
CH
groupsappearasnegative
peaks
in
the
DEPT-135.
This
is thebelongtothequaternarycarbonat
position
2.
The
DEPT-90experiment
gives
only
signal2
to confirm the peak assignment shown in Figure
7. case for the pea
The 13C DEPT experiment uses polarisation
at
60
ppm,
which
must
therefore
belongtothecarbonat
position2.
By
combining
the throf CH groups,
the DEPT-45
givesignalsof CH,
CHbelong
2 and3 groups,
Thepeaks
at 144
andCH
123
ppm
to thetransfer between
protonwhilst
and carbon
nuclei andandDEPT-135
spectra, it is possible
to confirm
thepeak
assignmentshown in Figure 7. The peaks
but forthe spectral
CH2 groups
appearas DEPT
negative
DEPT-135.
This
is thecase
the6,peak
methynegroupsat positions
7forandand the peaks
can be used
editing.
Onlycarbonspeaks in the
at
144
and
123
ppm
belongtothemethynegroupsat
positions
7 and 6, and the peaks at 1
at 60 ppm,
which mustat position
2. belong
By combining
the threegroups
at 18 and14 ppmto the methyl
atdirectly attached
to protons
are therefore
visible in belong to the carbon
and14 ppmbelong assignment
to the methylgroups at positions 8 and 1.
DEPT spectra,
it ispossible
confirm
8 shown
and 1. in Figure 7. The peaks
these experiments.
Since
the
peak atto167
ppmthe peak positionsat 144inand
ppmspectra
belong to
the methyne groups at positions 7 and 6, and the peaks at 18
does not show
the123DEPT
it mustand14
ppm
belongtothemethylgroupsbelong to the quaternary carbon at position
4. at positions 8 and 1.
The DEPT-90 experiment gives only signal of CH
groups, whilst the DEPT-45 and DEPT-135 give
7

7

6

4

6

2

2

8

1

4

Figure 7: Carbon spectra of 25% ethyl crotonate in CDCl3 (v/v).

Figure 7: Carbon spectra of 25% ethyl crotonate in CDCl3 (v/v).
Figure 7: Carbon spectra of 25% ethyl crotonate in CDCl3.

81

HETCORHETCORsignal along the direct dimension and the proton
Similar to the 2D COSY experiment, which detects
signal along the indirect dimension. The HETCOR
proton-proton coupling partners, a series ofSimilar to the 2D COSY experiment, which detects proton-proton coupling partners, aspectrum of 25% ethyl crotonate in CDCl3 isheteronuclear 2D NMR experiments have been
series of heteronuclear 2D NMR experiments have been devised to detect coupling
shown in Figure 8, with the 1D proton and carbon
devised to detect coupling partners of different
partners of different nuclei. The Heteronuclear Correlation (HETCOR) experiment is used
spectra from Figures 1 and 7 as vertical andnuclei. The Heteronuclear Correlation (HETCOR)
to correlate proton resonances to the carbons directly bonded to those protons. The
horizontal traces. The peaks in the 2D spectrum
experiment is used to correlate proton resonances
HETCOR experiment detects the carbon signal along the direct dimension and the proton
show which proton is bonded to which carbon.
to the carbons directly bonded to those protons.
signal along the indirect dimension.
The HETCOR experiment detects the carbon

The HETCOR spectrum of 25% ethyl crotonate in CDCl3 (v/v) is shown in Figure 8, withthe 1D proton and carbon spectra from Figures 1 and 7 as vertical and horizontal traces.
The peaks in the 2D spectrum show which proton is bonded to which carbon.

Figure 8: HETCOR spectrum of 25% ethyl crotonate in CDCl3 (v/v).

Figure 8: HETCOR spectrum of 25% ethyl crotonate in CDCl3.

HMQC
HMQC
The HMQC spectrum of 25% ethyl crotonate in
Another heteronuclear 2D correlation experiment
Another heteronuclear
2D correlation
experimentis theHeteronuclear Multiple Quantum
CDCl
is the Heteronuclear
Multiple Quantum
Coherence
3 is shown in Figure 9, with the 1D proton and
Coherence (HMQC)
to HETCOR,
it is usedfrom
to correlate
carbon spectra
Figuresproton
1 and 7 as horizontal(HMQC) experiment.
Similar toexperiment.
HETCOR, itSimilar
is usedresonancestothecarbons
directly
bondedtothoseprotons.
However,in peaks
the HMQC
and vertical traces. The
in the 2D spectrum
to correlate proton resonances to the carbons
experimentthecarbonsignalappearsalong
theindirectdimension,
andtheprotonsignalcarbon.
show which proton is bonded to which
directly bonded to those protons. However, in
along
the
directdimension.
the HMQC experiment the carbon signal appears
HMQC
spectrumandof 25%
ethyl crotonate
along the The
indirectdimension,
the proton
signal in CDCl3 (v/v) is shown in Figure 9, with the
1D
protonandcarbonspectrafrom
Figures
1 and 7 as horizontal and vertical traces. The
along the direct dimension.

peaks in the 2D spectrum show which proton is bonded to which carbon.

Figure 9: HMQC spectrum of 25% ethyl crotonate in CDCl3 (v/v).

Figure 9: HMQC spectrum of 25% ethyl crotonate in CDCl3.

HMBC

HMBC

HMBC
The HMQC experiment shown on the previous page was designed to correlate protons andcarbons which are connected through a one bond coupling. To obtain long-range protonThe
HMQC
experimentshown
on
the previous
page
was designed
towhichcorrelate
protonsvia
andcarboncorrelations
two orto
threebondcarbons
couplings,
theHeteronuclear
are throughconnected
a long-rangeMultiple Bond
The HMQC experiment shown on the previous
Correlation(HMBC)
experimentcan belong-range
used.Like inprotonthe HMQC experiment the carbon
carbonswhich
areconnected
throughaone
bond
coupling.
Toobtaincoupling. The couplings between molecular
page was designed to correlate protons andalong the indirect
dimension, andthe proton
signal along the direct
carbon correlations through two orsignal
threeappears
bond couplings,
the Heteronuclear
MultipleBondpositions look similar to the ones found from thecarbons which are connected through a one
bonddimension.
Correlation (HMBC) experiment can be used.Like in the HMQC experiment the carbon
COSYofspectrum,
but the HMQC
additionallycoupling. To obtain long-range protoncarbon
The HMBC andspectrum
25%signal
ethyl crotonate
CDCl3 (v/v)
is shown inshows
Figure 10, withsignal appears along the indirect dimension,
the proton
along theindirect
the 1D proton andcarbon spectrafrom Figurescarbons,
1 and 7 as whichhorizontal
andvertical traces.
couplings
toquaternaryarenotcorrelations through
two
or
three
bond
couplings,
dimension.
The peaks in thevisible
2D spectrum
show
which
protons
areForconnected
to whichcarbons via a
in
the
COSY
or
HMQC.
example,there
the Heteronuclear
Multiple
Bond
Correlation
The HMBC spectrum of 25% ethyllong-range
crotonatecoupling.
in CDClTheis shown
in Figure
10, with
3 (v/v)
couplings
betweenmolecular
positions look similar to the onesaremultibondand
couplings
from the carbon at(HMBC) experimentcan beLikein thethe 1D proton
andused.
carbonspectrafrom Figures
andclear
7spectrum,
as horizontal
verticaltraces.
foundfrom the1COSY
but the HMQC
additionallyshows couplings to quaternary
position4
tothe
protonsat
positions
7 andthere
2, are clear
HMQC experimentthecarbonsignalappears
The peaks in the 2D spectrum show
whichwhich
protons
connected
whichorcarbons
carbons,
are arenot visible
in thetoCOSY
HMQC.via
Foraexample,
markedasblue
in Figure10.
along the indirect
dimension,
andprotonsignal couplings
long-range
coupling.
Thethecouplings
betweenmolecular
positionslooksimilarones
multibandfrom
thedark
carbonat position
4totothetheprotons at positions 7 and 2,
markedas dark bluein Figure shows
10.
found
from the COSY
spectrum,but
the HMQC
additionallycouplings to quaternaryalong the direct
dimension.
The HMBC
spectrumwhich
are not
visiblein theCOSY or HMQC. For example, there are clearof 25% ethylcarbons,
crotonatein CDCl
shown
in Figure
3 ismultibandfromspectra
the carbon
at position 4 to the protons at positions 7 and 2,
10, with the 1D
protoncouplingsand carbon
frommarked
as
dark
blue
in
Figure10.
Figures 1 and 7 as horizontal and vertical traces.
The peaks in the 2D spectrum show which protons

Figure 10: HMBC spectrum of 25% ethyl crotonate in CDCl3 (v/v).

Figure 10: HMBC spectrum of 25% ethyl crotonate in CDCl3 (v/v).

Figure 10: HMBC spectrum of 25% ethyl crotonate in CDCl3.

R

Specifications• Frequency: 42.5 MHz Proton, 10.8 MHz Carbon• Resolution: 50% linewidth < 0.7 Hz (16 ppb)
• Lineshape: 0.55% linewidth < 20 Hz• Dimensions: 58 x 43 x 40 cm• Weight: 55 kg• Magnet: Permanent and cryogen free
• Stray field: < 2 G all around system

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have made. This makes their undergraduate experiment more applicable to both research and industry settings andincreases their enthusiasm for Chemistry.”
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