N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
188
5 1 H NMR
Effect of Substituents on 1 H Chemical Shifts of Monosubstituted Benzenes (in
ppm)
Substituent R
Z 2
Z 3
Z 4
–CH 3
-0.17
-0.09
-0.17
–CH 2 CH 3
-0.14
-0.05
-0.18
–CH(CH 3 ) 2
-0.13
-0.08
-0.18
–C(CH 3 ) 3
0.05
-0.04
-0.18
–CF 3
0.19
-0.07
0.00
–CCl 3
0.55
-0.07
-0.09
–CH 2 OH
-0.07
-0.07
-0.07
–CH=CH 2
0.08
-0.02
-0.09
–CH=CH–phenyl (trans)
0.16
0.00
-0.15
–C– – – CH
0.16
-0.01
-0.01
–C– – – C–phenyl
0.20
-0.04
-0.07
–phenyl
0.22
0.06
-0.04
–2-pyridyl
0.73
0.09
0.02
–F
-0.31
-0.03
-0.21
–Cl
-0.01
-0.06
-0.12
–Br
0.15
-0.12
-0.06
–I
0.36
-0.24
-0.02
–OH
-0.51
-0.10
-0.41
–OCH 3
-0.44
-0.05
-0.40
–OCH 2 CH=CH 2
-0.45
-0.13
-0.43
–O–phenyl
-0.33
-0.02
-0.25
–OCOCH 3
-0.26
0.03
-0.12
–OCO–phenyl
-0.12
0.10
-0.06
–OS(O) 2 CH 3
-0.05
0.07
-0.01
–NH 2
-0.67
-0.20
-0.59
–NHCH 3
-0.73
-0.16
-0.64
–N(CH 3 ) 2
-0.60
-0.10
-0.62
–N(phenyl) 2
-0.26
-0.10
-0.34
–N + (CH 3 ) 3 I –
0.72
0.40
0.34
–NHCHO (trans to O)
-0.25
0.03
-0.13
–NHCHO (cis to O)
-0.20
0.21
-0.01
–N(CH 3 )CHO
-0.16
0.07
-0.05
–NHCOCH 3
0.15
-0.02
-0.23
–NHCSNH 2
0.14
0.07
-0.14
C
X
O
N
R
1
2
3
4
δ H i
= 7.34 + Z i