N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
183
5.4 Alicyclics
183
5.4 Alicyclics
1 H Chemical Shifts and Coupling Constants of Saturated Alicyclic
Hydrocarbons (δ in ppm, J in Hz)
2 J gem -13.7
3 J ab 1.0
4 J ac -0.3
3 J ad,cis 1.8
3 J ad,trans 4.6
3 J bc
2.8
2 J gem,a -12.8
3 J ab,cis 9.3
3 J ab,trans 5.7
2 J gem,b -16.1
3 J bc
2.3
4 J bd
-2.3
5 J be,cis 2.1
5 J be,trans 3.0
3 J cd
5.8
3 J ab 5.1
5 J ac 0.5
5 J ad 1.4
4 J ae 1.3
3 J af 2.0
4 J bc -0.2
4 J bd -0.4
4 J be 2.0
2 J cd 0.1
3 J ab 9.7
4 J ac 1.0
5 J ad 1.1
3 J bc 5.1
0.20
1.51
5.66
6.53
5.67
5.79
2.12
1.50
1.75
5.79
2.08
6.23
5.89
6.43
2.27
6.28
5.69
1.99
1.60
1.79
2.80
5.95
2.57
0.92
7.01
1.44
1.94
At -100 °C
H ax 1.12
H eq 1.60
2 J gem -4.3
3 J cis 9.0
3 J trans 5.6
3 J ab ≈10
3 J bc 1.5
3 J ab ≈10
3 J bc 3.7
In derivatives:
2 J gem -3 to -9
3 J cis 6 to 12
3 J trans 2 to 9
Throughout:
J cis > J trans
In derivatives:
2 J gem -8 to -18
3 J cis 5 to 10
3 J trans 5 to 10
In derivatives:
3 J ab 1.5 to 2.0
3 J bc 0.5 to 1.5
In derivatives:
2 J gem -10 to -17
3 J cis
4 to 12
3 J trans 2 to 10
4 J cis ≈ 0
4 J trans ≈ -1
In derivatives:
2 J gem -11 to -14
3 J ax,ax 8 to 13
3 J eq,ax 2 to 6
3 J eq,eq 2 to 5
Generally:
J eq,ax ≈ J eq,eq +1
3 J ab 1.3
4 J ac -1.5
3 J bc 5.0
4 J bd 1.1
5 J be 2.0
3 J cd 1.9
H
H
a
a
a
a
a
b
b
c
c
e
d
d
b
c
d
e
f
a
a
b
b
b
c
d
e
e
d
d
c
c
a
b
c
d
b
c