N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
223
5.10 Sulfur Compounds
223
5.10 Sulfur Compounds
5.10.1 Thiols
1 H Chemical Shifts and Coupling Constants (δ in ppm, J in Hz)
Typical ranges of SH chemical shifts:
alk–SH
1–2
SH
2–4
The exchange with other SH, OH, NH, or COOH protons is generally so slow that
the chemical shift is characteristic and the vicinal coupling with SH protons becomes visible (5–9 Hz in aliphatic systems with fast rotation).
SH
a
b
c
d
e
H
SH
H
H
H
H
H
H
CH 3 SH
SH
SH
SH
SH
SH
SH
H
H
H
H
H
H
SH
H
H
H
H
H
7.18
3.40
7.10
7.04
3 J ab 7.9
4 J ac 1.2
5 J ad 0.6
4 J ae 2.1
3 J bc 7.5
4 J bd 1.5
2.00 1.26
1.39
1.82
1.62
3.19
1.59*
2.04*
1.51**
*; **: assignments uncertain
1.79**
1.32*
* in DMSO: 2.17
2.52
1.33
1.56
1.34
3.16
2.50
1.31
1.43
1.59
1.51
2.79
2.01
3.43
1.9
1.5
1.34
1.31
1.75
1.22
1.61
1.43
0.92
1.63
0.99
2.44
J vic 7.4
3 J ab 5.7
(in benzene)
a
b