Chapter 13

Nuclear Magnetic Resonance Spectroscopy

(NMR)

游聲盛 (Sheng-Sheng Yu)

成大化工系

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 What is spectroscopy?

• Spectroscopy is the study of

the interaction of
electromagnetic radiation
with matter.
• Nuclear magnetic resonance
spectroscopy is the use of the
NMR phenomenon to study
physical, chemical, and
biological properties of matter.
• You may have heard UV-Vis or
IR spectroscopy. NMR is
similar.

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 What is spectroscopy?

UV-Vis FT-IR

Mass spec

Detailed analysis on chemical structures,

stereochemistry… are often impossible.

Jacobsen, Neil E.. NMR Data Interpretation

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© 2017 Pearson Education, Ltd. Explained. Wiley.
 Possibility of a molecules C4H6O

Possible ways to determine the molecular structure:

FTIR, Raman, Mass spec… and NMR.

Jacobsen, Neil E.. NMR Data Interpretation

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© 2017 Pearson Education, Ltd. Explained. Wiley.
 NMR Spectroscopy

• You could have a whole lifetime in NMR!

• The main application is to molecular

fingerprinting: NMR is the primary tool that lets
chemists know they have the right structure.

• Quantitative analysis is also possible.

• Here, we will only review some basic principles of

NMR.

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 • How about Magnetic resonance imaging, MRI
(磁共振造影)?
• Same phenomenon, but used in a different way!

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 13-1 Introduction

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 Introduction

• Nuclear magnetic resonance spectroscopy (NMR) is

the most powerful tool available for organic structure
determination.
• It is used to study a wide variety of nuclei:
– 1H
– 13C Proton (1H) and carbon (13C) spectra are the
– 15N most common tools for organic chemistry.
– 19F
– 31P

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 13-2 Theory of Nuclear Magnetic
Resonance

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 Nuclear Spin

• A nucleus with an odd atomic number or an

odd mass number has a nuclear spin.
• The spinning, charged nucleus generates a
magnetic field called magnetic moment.

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 External Magnetic Field

• An external magnetic field (B0) applies a force to a small bar

magnet, twisting the bar magnet to align it with the external
field.
• The arrangement of the bar magnet aligned with the field is
lower in energy than the arrangement aligned against the
field.

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 Energy level

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 Proton Magnetic Moments

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 Two Energy States

• A nucleus is in resonance
when it is irradiated with
radio-frequency photons
having energy equal to the
energy difference between
the spin states.
• Under these conditions, a
proton in the alpha-spin
state can absorb a photon
and flip to the beta-spin
state.
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 E and Magnet Strength

• Energy difference is directly proportional to

the magnetic field strength.
ℎ
∆𝐸 = ℎ𝑣 = 𝛾 𝐵0 ∆𝐸 = Energy level difference between alpha
2𝜋 and beta state.
ℎ = Planck’s constant.
𝐵0 𝐵0 = Strength of the external magnetic field.
𝑣=𝛾 𝛾 = Gyromagnetic ratio. For proton, 𝛾 is 26,753
2𝜋 sec-1gauss-1.

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 Example

• A magnet generates a B0 of 7.046 Tesla.

• The gyromagnetic ratio of a proton
(γ)=2.675×108 T-1s-1.
 B0 2.675 10 -1 -1 8
v= = T s  7.046T
2 2  3.1416
=300  10 Hz 6

NMR spectrometers are often named by

= 300MHz their 1H operating frequency.

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 NMR = Low-energy spectroscopy

/nm /MHz Wavenumbers/cm-1 Probes

UV 200 1,500,000,000 50000 Electronic
Visible 500 600,000,000 20000 Electronic
Near Infrared 1000 300,000,000 10000 Vibrational
Infrared 5000 60,000,000 2000 Vibrational
Microwave Rotational
NMR 300000000 1,000 0.033 Nuclear Spin
DLS NA:  <1 NA:  Translation
Today’s biggest NMR is about 900 MHz

The energies associated with nuclear spin flips (from + to -) are much less than
the thermal energy, kT: E+ - E-  0. This is true even in high magnetic fields

Unlike vibrational & electronic

( E + −E − ) spectroscopy, most molecules
N+ −
=e kT
1 are not in the ground state. In
fact, only a tiny excess of
N− molecules is in the ground state.
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 13-2 Theory of Nuclear Magnetic
Resonance

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 Magnetic Shielding

• If all protons absorbed the same amount of

energy in a given magnetic field, not much
information could be obtained.

• But protons are surrounded by electrons that

shield them from the external field.

• Circulating electrons create an induced magnetic

field that opposes the external magnetic field.

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 Induced Magnetic Field

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 Shielded Protons

• A naked proton will absorb at 70,459 gauss.

• A shielded proton will not absorb at 70,459 gauss, so the
magnetic field must be increased slightly to achieve resonance.
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 Protons in a Molecule

• Protons in different chemical environments are shielded

by different amounts.
• The hydroxyl proton is not shielded as much as the
methyl protons, so the hydroxyl proton absorbs at a
lower field than the methyl protons.
• We say that the proton is deshielded somewhat by the
presence of the electronegative oxygen atom.
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 13-4 The NMR Spectrometer

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 The NMR Spectrometer

• The original continuous wave (CW) NMR spectrometer

“scans” different magnetic fields.

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 The NMR Graph

downfield upfield

• The more shielded methyl protons appear toward the

right of the spectrum (higher field); the less shielded
hydroxyl proton appears toward the left (lower field).
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 Fourier Transform NMR

• A radio-frequency pulse is given to excite all spins.

• Nuclei absorb energy and precess (spin) like
little tops.
• A complex signal is produced and then decays as the nuclei
lose energy.
• Free induction decay (FID) is converted to a spectrum.

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 Free induction decay (FID)

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 Fourier transform

Fourier transform is a
mathematical transformation
between time/space domains to a
frequency domain.

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 How does the instrument look like?

NCKU’s 700 MHz NMR

spectrometer.

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 The magnet

• Use persistent superconducting magnets to generate the B0

field

• The wire is held at a sufficiently low temperature (typically

6 K) for it to become superconducting (resistance goes to
zero).

• Generating a magnetic field without consuming any

electrical power.

• Superconducting magnets tend to be very stable and so are

ideal for NMR.

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 Sample tubes and sample preparation

• About 5–10 mg or 10 µl of the substance

are placed in the sample cell or NMR tube.

• NMR tube: A cylindrical glass tube about 17

cm long with a 5 mm outer diameter and
dissolved by the addition of about 0.5 ml of
solvent.

https://www.nmrtubes.com/secure-series.php
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 About the solvent

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 Deuterated solvents

For NMR, deuterated solvents are

preferred for two reasons.

• Lock the field (Maintaining the

same magnetic field strength).

• Reduce the proton signals from the

solvents (You have more solvent
molecules than your target
compound!)

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 13-5 The Chemical Shift

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 1H NMR

• The most popular spectra and the starting point

for more advanced analysis.

1. The range of chemical shift (化學位移).

1. Shielding and deshielding.
2. Electronegative atoms (O, N…)
3. Double bonds
2. J coupling.

3. Integrals.

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 NMR Signals

• The number of signals shows how many different kinds

of protons are present.

• The location of the signals shows how shielded or

deshielded is the proton.

• The intensity of the signal shows the number of

protons of that type.

• Signal splitting shows the number of protons on

adjacent atoms.

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 Tetramethylsilane (TMS)

• TMS is added to the sample

as an internal standard.
• Since silicon is less
electronegative than carbon,
TMS protons are highly
shielded.
• The TMS signal is defined as
0.00 ppm.
• Organic protons absorb
downfield (to the left) of the
TMS signal.
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 Chemical Shift

• The variations in the positions of NMR absorptions,

arising from electronic shielding and deshielding, are
called chemical shifts.

• The chemical shift (in ppm) is independent of the

spectrometer used.
• Most common scale is the δ (delta) scale.

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 Fourier transform

Recall our previous discussion

about FT.

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 Using propyl acetate as an example

a. 400.130821 – 400.13 MHz = 821 Hz

b. 400.131610 – 400.13 MHz = 1610 Hz
c. 400.130661 – 400.13 MHz = 661 Hz
d. 400.130378 – 400.13 MHz = 378 Hz

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 Scale the spectra

a. 821 Hz/400.13 MHz = 2.051 parts per million (ppm)

b. 1610 Hz/400.13 MHz = 4.024 ppm
c. 661 Hz/400.13 MHz = 1.651 ppm
d. 378 Hz/400.13 MHz = 0.944 ppm

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 Scale the spectra

Downfield: Shift to the left, to higher

resonant frequencies and larger ppm d
values. b
Upfield: Shift to the right, to lower
resonant frequencies and smaller ppm
values. c

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 Delta Scale

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 Variation of Chemical Shift

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 Electronegative Atoms

• More electronegative atoms

deshield more and give
larger shift values.
• Additional electronegative
atoms cause an increase in
chemical shift.

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 Location of Electronegative Atoms

• The deshielding effect of an electronegative substituent

drops off rapidly with distance.

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 Typical Values

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 Magnetic Fields in Aromatic Rings

• The induced magnetic field of

the circulating aromatic
electrons opposes the applied
magnetic field along the axis
of the ring.

• Protons in the region where

the induced field reinforces
the applied field are
deshielded and will appear at
lower fields in the spectrum
between  7–8.

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 Magnetic Fields in Aromatic Rings

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 Magnetic Field of Alkenes

• The pi electrons of the alkene generate a magnetic field that

opposes the applied magnetic field in the middle of the molecule
but reinforces the applied field on the outside where the vinylic
protons are located.
• This reinforcement will deshield the vinylic protons, making them
shift downfield in the spectrum to the range of  5–6.
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 Magnetic Fields of Alkynes

• When the terminal triple

bond is aligned with the
magnetic field, the cylinder
of electrons circulates to
create an induced magnetic
field.
• The acetylenic proton lies
along the axis of this field,
which opposed the external
field.
• The acetylenic protons are
shielded and will be found
at  2.5.
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 Deshielding of the
Aldehyde Proton

pi bond + electron-withdrawing

• Like a vinyl proton, the aldehyde proton is deshielded by the

circulation of electrons in the pi bond.
• It is also deshielded by the electron-withdrawing effect of the
carbonyl (C═O) group, giving a resonance between
 9 and 10.
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 O—H and N—H Signals

• The chemical shift of the acidic protons

depends on concentration.

• Hydrogen bonding in concentrated solutions

deshields the protons, so the signal is around
 3.5 for N—H and  4.5 for O—H.

• Proton exchanges between the molecules

broaden the peak.
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 Carboxylic Acid Proton

• Because of the high polarity of the

carboxylic acid O—H bond, the signal for
the acidic proton will be at shifts greater
than  10.
• Labile protons are often unreliable for
structural determination! 54
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 13-6 The Number of Signals

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 Number of Signals

• Methyl tert-butyl ether has two types of protons, giving

two NMR signals.
• Chemically equivalent hydrogens have the same
chemical shift. All the methyl groups of the tert-butyl
group are equivalent and they produce only one signal.
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 tert-Butyl Acetoacetate

• The spectrum of tert-butyl acetoacetate has only three

signals.
• The most shielded protons are the methyl groups of the
tert-butyl. The most deshielded signal is the methylene
(CH2) because it is in between two carbonyl groups.
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 o-xylene, accidentally equivalent protons

• o-xylene should have three signals, but only two peaks

appear on the spectrum.
• Sometimes the effect of substituent is not obvious and
the resolution of NMR spectrometer is not high enough
to differentiate peaks.
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 Solved Problem 2
Using Table 13-3, predict the chemical shifts of the protons in the following compounds.

Solution
(a) The methyl group in acetic acid is next to a carbonyl group; Table 13-3 predicts a
chemical shift of about  2.1. (The experimental value is  2.10.) The acid proton (—
COOH) should absorb between  10 and  12. (The experimental value is
 11.4, variable.)
(b) Protons a are on the carbon atom bearing the chlorine, and they absorb between  3 and
 4 (experimental:  3.7). Protons b are one carbon removed, and they are predicted to
absorb about  1.7, like the β protons in 1-bromobutane (experimental:  1.8). The
methyl protons c will be nearly unaffected, absorbing around  0.9 ppm (experimental: 
1.0).
(c) Methyl protons a are expected to absorb around  0.9 (experimental:  1.0). The vinyl
protons b and c are expected to absorb between  5 and  6 (experimental:  5.8 for b
and  4.9 for c).

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 13-7 Areas of the Peaks

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 Intensity of Signals: Integration

• The amount the integral trace rises is proportional to

the area of that peak.
• The integration will have a trace for the tert-butyl
hydrogens that is three times as large as the trace for
the methyl hydrogens. The relative area for methyl and
tert-butyl hydrogens is 1:3.
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 13-8 Spin-Spin Splitting

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 Spin-spin coupling or J coupling

• Nonequivalent protons on adjacent carbons have

magnetic fields that may align with or oppose the
external field.

• This magnetic coupling causes the proton to absorb

slightly downfield when the external field
is reinforced and slightly upfield when the external
field is opposed.

• All possibilities exist, so the signal is split.

This splitting of signals into multiplets is called spin-
spin splitting.

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 1,1,2-Tribromoethane

• Spin-spin splitting is a reciprocal property. If one proton splits another, the

second proton must split the first.

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 Doublet: One Adjacent Proton

• Hb can feel the alignment of

the adjacent proton Ha.

• When Ha is aligned with the

magnetic field, Hb will be
deshielded.

• When Ha is aligned against

the magnetic field, Hb will
be shielded.

• The signal is split in two and

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is called a doublet. 66
 Triplet: Two Adjacent Protons

• When both Hbs are aligned

with the magnetic field, Ha will
be deshielded.

• When both Hbs are aligned

against the magnetic field, Ha
will be shielded.

• It is more likely that one Hb

will be aligned with the field
and the other Hb against the
field. The signal will be at its
normal position.

• The signal is split in three and

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 The N + 1 Rule

• If a signal is split by N equivalent protons, it is split

into N + 1 peaks.

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 Spin-Spin Splitting Distance

• Equivalent protons do not split each other.

• Protons bonded to the same carbon will split

each other if they are nonequivalent.

• Protons on adjacent carbons normally will split

each other.

• Protons separated by four or more bonds will not

split each other.

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 Long-Range Coupling

• When the hydrogen atoms are four bonds or more

apart, spin-spin splitting is not normally observed.
When it actually does occur, it is called long-range
coupling.

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 Splitting for Ethyl Groups

• The hydrogens on the CH3 are affected by the two neighboring hydrogens on
the adjacent CH2 group. According to the N + 1 rule, the CH3 signal will be split
into (2 + 1) = 3. This is a triplet.
• The hydrogens on the CH2 group are affected by the three hydrogens on the
adjacent CH3 groups. The N + 1 rule for the CH2 signal will be split into (3 + 1) =
4. This is called a quartet.
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 Splitting for Ethyl Groups

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 Leaning of a Multiplet

• Another piece of information: Leaning.

• A multiplet “leans” toward the signal of
protons responsible for splitting.

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 Splitting for Isopropyl Groups

• The hydrogen on the CH has six adjacent hydrogens. According to

the N + 1 rule, the CH signal will be split into (6 + 1) = 7. This is
called a septet.
• The two CH3bs are equivalent, so they give the same signal. They
have one adjacent hydrogen (CH), so their signal will be N + 1, 1 +
1 = 2 (doublet).
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 Typical isopropyl group pattern

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 Solved Problem 3
Propose a structure for the compound of molecular formula C4H10O whose proton NMR spectrum
follows.

Solution
The molecular formula C4H10O indicates no elements of unsaturation. Four types of hydrogens appear
in this spectrum, in the ratio 2:1:1:6. The singlet (one proton) at  2.4 might be a hydroxy group, and
the signal (two protons) at  3.4 corresponds to protons on a carbon atom bonded to oxygen. The 
3.4 signal is a doublet, implying that the adjacent carbon atom bears one hydrogen.

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 Solved Problem 3 (Continued)
Solution (Continued)
(Since we cannot be certain that the  2.4 absorption is actually a hydroxy group, we might consider
shaking the sample with D2O. If the 2.4 ppm absorption represents a hydroxy group, it will shrink or
vanish after shaking with D2O.)
The signals at  1.8 and  0.9 resemble the pattern for an isopropyl group. The integral ratio of 1:6
supports this assumption. Because the methine proton of the

isopropyl group absorbs at a fairly high field, the isopropyl group must be bonded to a carbon atom
rather than an oxygen.

Our two partial structures add to a total of six carbon atoms (compared with the four in the
molecular formula) because two of the carbon atoms appear in both partial structures. Drawing the
composite of the partial structures, we have isobutyl alcohol:

This structure must be rechecked to make sure that it has the correct molecular formula and that it
accounts for all the structural evidence provided by the spectrum (Problem 13-23).
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 Coupling Constants

• The coupling constant is the distance between

the peaks of a multiplet (in Hz).

• Coupling constants are independent of

strength of the external field.

• Multiplets with the same coupling constants

may come from adjacent groups of protons
that split each other.
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 Values for Coupling Constants

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 Proton NMR for p-Nitrotoluene

a
b

• para-Nitrotoluene has two pairs of equivalent aromatic protons

a and b. Since the coupling constant for ortho hydrogens is
approximately 8 Hz, the peaks of the signal will be separated by
around 8 Hz. Good indication for ortho and meta isomers!
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 Vinylic Coupling Constants

b
a

a b

• There are two vinylic protons in 4,4-dimethylcyclohex-2-ene-1-

one, and they are cis.
• The coupling constant for cis coupling is approximately 10 Hz, so
the peaks should be separated by that amount.
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 Chemical Shift of unsaturated carbonyl
compound

Observed at very high ppm (~7)

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 Vinylic Coupling Constants

a b

• The 15 Hz coupling constant suggesting trans configuration.

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 13-9 Complex Splitting

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 Complex Splitting

• Signals may be split by

adjacent protons that are
different from each other
with different coupling
constants.
• Example: Ha of styrene is
split by an adjacent Hb
trans to it (J = 17 Hz) and
an adjacent Hc cis to it (J =
11 Hz).

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 1H-NMR Spectrum of Styrene

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 Splitting Tree for Styrene

Not quartet,
but doublet of
doublets!

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 1H-NMR Spectrum of 1-iodopropane

• Signal for Hb looks more complicated than expected. Jab and Jbc are similar, but not
the same!

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 13-10 Stereochemical
Nonequivalence of Protons

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 Stereochemical Nonequivalence

• If the replacement of each of the protons of a —CH2

group with an imaginary “Z” gives stereoisomers, then
the protons are nonequivalent and will split each other.
For ethanol, replacing each
methyl proton by an
imaginary Z groups leads to
the same compound. ie,
these protons will not split
each other.!

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 Diastereotopic Vinylic Protons

• Replacing the cis hydrogen gives the cis diastereomer, and

replacing the trans hydrogen makes the trans diastereomer.
• Because the two imaginary products are diastereomers, these
protons are called diastereotopic protons.
• Diastereotopic hydrogens are capable of splitting each other.

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 Stereochemical relationships
in a cyclic system

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 Diastereotopic Protons for saturated system

• The two protons on the —CH2Cl group are

diastereotopic; their imaginary replacements give
diastereomers.
• Diastereotopic protons are usually vicinal to
stereocenters (chiral carbons).
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 Newman projection

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 1H-NMR Spectrum of 1,2-Dichloropropane

• Proton NMR spectrum of 1,2-dichloropropane shows distinct

absorptions for the methylene protons on C1.
• These hydrogen atoms are diastereotopic and are chemically
nonequivalent.
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 13-11 Time Dependence of NMR
Spectroscopy

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 Time Dependence

• Molecules are tumbling relative to the magnetic

field, so NMR is an averaged spectrum of all the
orientations.

• Example:
– Axial and equatorial protons on cyclohexane
interconvert so rapidly that they give a single signal.

– Proton transfers for OH and NH may occur so quickly

that the proton is not split by adjacent protons in the
molecule.

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 Cyclohexane

Very fast at room temperature!

• Peak splitting of axial and equatorial protons is not

observable at room temperature (only one peaks!)

• The conformation change can be slowed down by

performing NMR experiment at low temperature. (Varying
temperature experiment!)

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Organic chemistry, fifth ed. by Paula Yurkanis Bruice.
 Hydroxyl Proton in a
Pure Sample

• Ultrapure samples of ethanol show splitting.

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 Hydroxyl Proton in an
Impure Sample

• Fast exchange rate: No splitting.

• Moderate exchange rate: Peak
broadening.
• Slow exchange rate: Splitting.

• Ethanol with a small amount of acidic or basic impurities will not

show splitting.
• Bases and acids catalyze the exchange of OH protons.
• Each OH proton becomes attached to a large number of different
ethanol molecules and experiences all possible spin arrangement!
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 N—H Proton

• The acidic proton on the nitrogen has a moderate rate

of exchange.
• The peak may be broad.

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 Identifying the O—H
or N—H Peak

• Chemical shift of dissociable protons will depend on

concentration and solvent. (NOT reliable for structural
elucidation!)
• To verify that a particular peak is due to O—H or N—H, shake
the sample with D2O to exchange the H for a D.
• The deuterium is invisible in the proton NMR, so the original
signal for the OH will disappear.

R—O—H + D—O—D R—O—D + D—O—H

R—NH2 + 2 D—O—D R—ND2 + 2 D—O—H

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 13-12 Carbon-13 NMR
Spectroscopy

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 Carbon-13 NMR

• Why do we care? Consider a carbonyl group!

• Carbon-12 (12C) has no magnetic spin.
• Carbon-13 (13C) has a magnetic spin, but is
only 1% of the carbon in a sample.
• The gyromagnetic ratio of 13C is one-fourth of
that of 1H.
– 13C NMR has much lower sensitivity than 1H NMR!

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 Carbon Chemical Shifts

• Table of approximate chemical shifts values for 13C-

NMR: Most of these values for a carbon atom are about
15–20 times the chemical shift of a proton if it were
bonded to the carbon atom.
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 Combined 13C and 1H Spectra

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 Differences Between 1H and
13C Technique

• Resonance frequency is about one-fourth that

of hydrogen, 15.1 MHz instead of
60 MHz.

• Peak areas are not proportional to the number

of carbons.

• Carbon atoms with more hydrogens absorb

more strongly.
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 Proton decoupling

• The 13C peak is not split by nearby nuclei in the molecule because
of the dilute (low abundance) nature of 13C. Nearby hydrogen
atoms (1–3 bonds away from ) are 100% abundant and will split the
peak.

• This splitting would make the spectrum very complex and

overlapping, so we remove it with a process called proton
decoupling.
• While the FID is recorded, the protons are gently irradiated with a
radio frequency signal at their resonant frequency, causing them to
rapidly flip between the “up” (aligned) and “down” (opposed)
states.
• From the point of view of any nearby nucleus, the splitting effect of
the protons is averaged to a blur, as if the proton were neither “up”
nor “down”, and this removes the splitting effect.
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 Proton decoupled 13C NMR

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 Off-Resonance Decoupling
13C-NMR

• 13C
nuclei are split only by the protons attached
directly to them.
• The N + 1 rule applies: A carbon with N number of
protons gives a signal with N + 1 peaks.
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 DEPT 13C NMR

• DEPT (Distortionless Enhanced Polarization

Transfer) provides the same information as
off-resonance decoupling.
• Easier to run with Fourier-transform
spectrometers
• Each 13C nucleus is magnetically coupled to
the protons bonded to it.

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 Information from 13C DEPT

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 13-13 Interpreting Carbon NMR
Spectra

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 Interpreting 13C NMR

• The number of different signals indicates the

number of different kinds of carbon.
• The location (chemical shift) indicates the
type of functional group.
• The splitting pattern of an off-resonance,
decoupled spectrum indicates the number of
protons attached to the carbon.

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 Take δ-valerolactone as an example

Off resonance-
decoupled

Usually, same
Broadband- information
decoupled can also be
obtained by
DEPT spectra.

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 Take δ-valerolactone as an example

173 ppm falls in the common range of carbonyl

groups. Off-resonance spectrum also confirms
that no protons attach to this carbon.

70 ppm is common chemical shift for carbon

bonded to an electronegative element
(oxygen). It is also a triplet in Off-resonance
spectrum (CH2)

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 30 ppm is common chemical shift for carbon bonded to an
carbonyl group. It is also a triplet in Off-resonance spectrum
(CH2)

The two signals at 22 ppm and 19 ppm are carbons without

any deshielding groups. The one at 22 ppm may be close to an
oxygen.

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 Interpreting 13C NMR

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 Short summary!

• The molecular formula, C5H8O2, indicating two elements of unsaturation.

• We have identified one unsaturation as the carbonyl groups.
• No double or other carbonyl, the remaining unsaturation must be a ring!

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 13-14 Nuclear Magnetic
Resonance Imaging

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 Magnetic Resonance
Imaging (MRI)

• Nuclear magnetic resonance imaging is a

noninvasive diagnostic tool.
• “Nuclear” is omitted because of the public’s
fear that it would be radioactive.
• A computer puts together “slices” to get
3-D images.
• Tumors are readily detected.

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 MRI Image

• Watery tissues, fatty tissues, and bone can be

identified by their relaxation times (Important, but
not covered in this class!). These difference
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 Take away of Chapter 13
• What is the NMR phenomenon? 1H and 13C NMR.

• Meaning of chemical shift?

– Shield nuclei
– Electron-withdrawing groups
– pi bonds

• The integral of 1H NMR?

• What is peak splitting (J coupling)? What kind information can you obtain?

• Stereochemical Nonequivalence of Protons

NMR is one of tool you can use to identify unknown
• Time dependence of NMR? compounds. Often, we use multiple tools together
(Mass spec, IR, NMR..)
• 13C NMR
– Proton decoupled The “problem-solving strategy” on page 697 is very
– DEPT 13C NMR useful!
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