158 5 1H NMR

1H Chemical Shifts of Monosubstituted Alkanes (δ in ppm)

Substituent Methyl Ethyl 1-Propyl

C –CH3 –CH2 –CH3 –CH2 –CH2 –CH3
–H 0.23 0.86 0.86 0.91 1.33 0.91
C C C –CH=CH2 1.71 2.00 1.00 2.02 1.43 0.91
– C ––– CH 1.80 2.16 1.15 2.10 1.50 0.97
–phenyl 2.35 2.63 1.21 2.59 1.65 0.95
C C X –F 4.27 4.55 1.35 4.30 1.68 0.97
–Cl 3.06 3.47 1.33 3.47 1.81 1.06
–Br 2.69 3.37 1.66 3.35 1.89 1.06
–I 2.16 3.16 1.88 3.16 1.88 1.03
O –OH 3.48 3.71 1.24 3.59 1.59 0.94
–O–alkyl 3.24 3.37 1.15 3.27 1.55 0.93
–OCH=CH2 3.16 3.66 1.21
–O–phenyl 3.73 3.98 1.38 3.86 1.70 1.05
–OCOCH3 3.67 4.12 1.26 4.02 1.65 0.95
N
–OCO–phenyl 3.88 4.37 1.38 4.25 1.76 1.07
–OS(O)2–4-tolyl 3.70 4.07 1.30 3.94 1.60 0.95
Hal
N –NH2 2.47 2.66 1.11 2.65 1.46 0.91
–NHCH3 2.30
O –N(CH3)2 2.22 2.32 1.06
–NHCOCH3 2.79 3.26 1.14 3.18 1.55 0.96
–NO2 4.29 4.37 1.58 4.28 2.01 1.03
N –C––– N 1.98 2.35 1.31 2.34 1.70 1.08
–NC 2.85 3.39 1.28
S S –SH 2.00 2.44 1.31 2.50 1.63 0.99
–S–alkyl 2.09 2.49 1.25 2.43 1.59 0.98
–SS–alkyl 2.30 2.67 1.35 2.63 1.71 1.03
C X –S(O)CH3 2.50
–S(O)2CH3 2.84 2.94 2.80

P Si O –CHO 2.20 2.46 1.13 2.37 1.64 0.97

|| –COCH3 2.17 2.44 1.06 2.40 1.60 0.93
–CO–phenyl 2.55 2.92 1.18 2.86 1.72 1.02
Natural C –COOH 2.10 2.36 1.16 2.31 1.68 1.00
Products –COOCH3 2.01 2.32 1.15 2.22 1.65 0.98
–CONH2 2.02 2.23 1.13 2.19 1.68 0.99
Solvents –COCl 2.66 2.93 1.24 2.87 1.74 1.00
 5.1 Alkanes 159

1H Chemical Shifts of Monosubstituted Alkanes (δ in ppm, contd.)

Substituent 2-Propyl n-Butyl tert-Butyl

–CH –CH3 –CH2 –CH2 –CH2 –CH3 –CH3 C
–H 1.33 0.91 0.91 1.31 1.31 0.91 0.89
C –CH=CH2 2.06 ≈1.5 ≈1.2 0.90 1.02
C C
–C ––– C– 2.59 1.15 2.18 1.52 1.41 0.92 1.24
–phenyl 2.89 1.25 2.61 1.60 1.34 0.93 1.32
X –F 4.84 1.34 4.34 1.65 0.95 1.34 C C
–Cl 4.14 1.55 3.42 1.68 1.41 0.92 1.60
–Br 4.21 1.73 3.42 1.84 1.46 0.93 1.76
–I 4.24 1.89 3.20 1.80 1.42 0.93 1.95
O –OH 4.02 1.21 3.64 1.56 1.39 0.94 1.26
–O–alkyl 3.55 1.08 3.40 1.54 1.38 0.92 1.24
–OCH=CH2 4.06 1.23 3.68 1.61 1.39 0.94
–O–phenyl 4.51 1.31 3.94 1.76 1.47 0.97
–OCOCH3 4.99 1.23 4.06 1.60 1.39 0.94 1.45
–OCO–phenyl 5.22 1.37 1.58 N
–OS(O)2–4-tolyl 4.70 1.25 4.03 1.62 1.36 0.88
N –NH2 3.07 1.03 2.69 1.43 1.35 0.92 1.15 Hal
–NHCOCH3 4.01 1.13 3.21 1.49 1.35 0.92 1.28
–NO2 4.44 1.53 4.47 2.07 1.50 1.07 1.59
–C ––– N 2.67 1.35 2.34 1.63 1.50 0.96 1.37 O
–NC 3.87 1.45 1.44
S –SH 3.16 1.34 2.52 1.59 1.43 0.92 1.43
N
–S–alkyl 2.93 1.25 2.49 1.56 1.42 0.92 1.39
–SS–alkyl 2.69 1.64 1.42 0.93 1.32
–S(O)2CH3 3.13 1.41 1.44 S
O –CHO 2.39 1.13 2.42 1.59 1.35 0.93 1.08
|| –COCH3 2.58 1.11 1.13
C X
–CO–phenyl 3.58 1.22 2.95 1.72 1.41 0.96
C –COOH 2.56 1.21 2.35 1.62 1.39 0.93 1.23
–COOCH3 2.56 1.17 2.31 1.61 1.33 0.92 1.20
P Si
–CONH2 2.44 1.18 2.22 1.60 1.37 0.93 1.22
–COCl 2.97 1.31 2.88 1.67 1.40 0.93
Natural
Products

Solvents