Proton Nuclear Magnetic Resonance Spectroscopy (1H-NMR)

If the proton is placed in an external magnetic field, the proton's magnetic moment becomes aligned with the external field (lower energy) or against it (higher energy).

No external magnetic field

With external magnetic field

Addition of energy (radio wave photons) results in nuclear spin flip:

Spin antiparallel to external field Energy

E = radio wave energy

Spin parallel to external field

Schematic NMR spectrum:

Intensity

NMR signal

downfield low magnetic field strength

upfield high magnetic field strength

Lecture Supplement: Proton NMR

External magnetic field

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Characteristic Proton NMR Chemical Shifts (ppm) RCH3 RCH2R acyclic RCH2R cyclic 0.9 1.3 1.5 RCCH RNHCH3 RCH2X (X = Cl, Br, I)
O

2.5 23 3.5

RCHO, ArCHO RNH2 ArNH2

O

9.5 11 13 35

R3CH
R R
O

1.5 2.0

ROCH3, R

3.8
OCH3

N H

59

CH3

1.8
R

R2C=CH2

5.0

ROH

15

2.0 2.3
R CH3

RCH=CR2

5.3

ArOH

47

ArCH3

2.3

ArH

6.5 - 8

RCO2H

10 13

The exact chemical shift for each proton type does not need to be memorized. This table will be provided on an exam if needed. Sample NMR spectra taken from Integrated Spectral Data Base System for Organic Compounds (www.aist.go.jp/RIODB/SDBS/menu-e.html)
1

H-NMR (ppm): 4.19 (singlet; integral = 1.0) 3.41 (singlet, integral = 3.0)

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Lecture Supplement: Proton NMR

H-NMR (ppm): 3.19 (singlet, integral = 1.0) 1.33 (singlet, integral = 1.0)

H-NMR (ppm): 3.43 (quartet, integral = 1.0) 1.68 (triplet, integral = 1.5)

H-NMR (ppm): 3.79 (septet, integral = 1.0) 1.31 (doublet, integral = 6.0)

Lecture Supplement: Proton NMR

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H-NMR (ppm): 3.39 (triplet, integral = 1.0) 1.87 (sextet, integral = 1.0) 1.03 (triplet, integral = 1.5)

H-NMR (ppm): 7.24 - 6.84 (multiplet, integral = 5.0) 5.35 (singlet, integral = 1.0)

H-NMR (ppm): 3.66 (singlet, integral = 1.0) 2.05 (singlet, integral = 1.0)

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Lecture Supplement: Proton NMR

H-NMR (ppm): 5.90 (quartet, integral = 1.0) 2.06 (doublet, integral = 3.0)

H-NMR (ppm): 5.66 (multiplet, integral = 1.0) 1.98 (multiplet, integral = 2.0) 1.16 (multiplet, integral = 2.0)

H-NMR (ppm): 7.38 - 7.00 (multiplet, integral = 1.7) 2.34 (singlet, integral = 1.0)

Lecture Supplement: Proton NMR

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H-NMR(ppm): 10.00 (singlet, integral = 1.0) 7.87 - 7.56 (multiplet, integral = 5.0)

H-NMR (ppm): 5.83 (doublet of doublets, integral = 1.0) 4.93 - 4.82 (multiple, integral = 2.0) 1.00 (singlet, integral = 9.0)

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Lecture Supplement: Proton NMR

Sample Problem #1

C10H14

Lecture Supplement: Proton NMR

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Sample Problem #2

C4H8O2

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Lecture Supplement: Proton NMR