N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
219
5.9 Nitrogen Compounds
219
5.9.3 Nitrites and Nitrates
1 H Chemical Shifts (δ in ppm)
5.9.4 Nitrosamines, Azo and Azoxy Compounds
1 H Chemical Shifts (δ in ppm)
H
NO 2
H
H
H
H
H
H
O NO 2
N
N
O
NO
7.84
7.57
7.63
a
b
c
d
e
NO 2
H
H
H
NO 2
NO 2
NO 2
H
H
H
H
H
H
4.91
2.26, 2.12
1.88, 1.70
1.85
1.28
4.38
2.23
1.38
1.85
1.67
1.62
4.43
2.60
8.27
7.60
7.73
5.87
6.55
2.96
3.76
1.15
1.52
0.97 1.75
1.75 0.93
1.39
3.53
4.07
1.39
4.89
4.26
7.12
4.78
1.41 4.71
1.37
5.19
1.59
4.39
1.06
4.52
1.39
0.96 1.72
1.78
1.37
a
a
b
b
c
c
d
e
3 J ab 8.4
4 J ac 1.2
5 J ad 0.4
4 J ae 2.4
3 J bc 7.5
4 J bd 1.5
3 J ab 7.9
4 J ac 1.3
5 J ad 0.6
4 J ae 2.0
3 J bc 7.4
4 J bd 1.4
3 J ab 7.0
3 J ac 14.6
2 J bc 1.4
Owing to hindered rotation around the N–NO bond, corresponding protons in cis
and trans positions have different chemical shifts in the neighborhood of the N=O
group.
In general: δ cis < δ trans for α-CH 3 , α-CH 2 , and β-CH 3
δ cis > δ trans for α-CH
N
N
O
N
N
O
O NO 2
O NO
O NO
O NO
O NO 2