C-13 NMR Spectroscopy

CHM 320 La Salle University

C-13 Spectrum of m-Nitroacetophenone

O CCH3

NO2

1H NMR Spectrum of Ethylbenzene

CH2CH3

Typical ppm (d) Ranges in C-13 NMR

Relaxation Times

Coupling Constants are Large

J Values measured in Hz

HC

CCH2CH2CH2CH3

HC

CCH2CH2CH2CH3

CH3CH2OCCH2CCH3

CH3CH2OCCH2CCH3

H2C=C=CHCH2CH2OH

CO2H

H3C H3C

O N CCH3

Silverstein, p. 212

Silverstein, p. 215

H3C H3C

OCH3 N CH OCH3

O H3C C C HC O H NHCCH3

O CF3COCH3

Predicting Chemical Shifts

Predicted Chemical Shifts of Ca and Cb

b a

Ca = (-2.5) + 4(9.1) + 9.4 + 2(-2.5) + 3(-1.5) + (-8.4) = ppm 25.4 base 4o(1o)
o 4 (2o)

Cb = (-2.5) + 2(9.1) + 5(9.4) +(-7.2) + (-2.5) = ppm 53.0 o base 2o(4o) 2 (3o)

2,2,4-Trimethylpentane
d 53.28, 31.10, 30.16, 25.51, 24.73

Chemical Shift Prediction with Functional Groups

Use Base Value From Table 4.5

Using Table 4.5 and 4.6 OH OH 34.7 + 41 = 75.7 OH 22.8 + 41 = 63.8 13.9 + 48 = 51.9 ppm

You can Choose Which Base Value from Table 4.5 to Use
OH OH OH OH

34.7 + 41 + (-5) + 3(9.4) + (-2.5) + (-7.2) = ppm 89.2 o C-3 -OH -OH 2o(3o) 2 (4o) 36.9 + 41 + (-5) + 2(9.4) + (-2.5) 88.8 ppm = C-3 -OH -OH 2o(3o)

Spectrum at 75 MHz and 150 MHz