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H
3
N
CO
2
H
3
N
CO
2
K
eq
+ H
p
K
a
= 8.18
SH
S
cysteine (CSH)
ClO
2
k
1
= 1.03 × 10
8
/M/s
ClO
2
H
3
N
CO
2
S
fast
+ ClO
2
H
3
N
CO
2
O
O
S
Cl
l
o
p
p
h
y
cysteinyl-ClO
2
adduct
h
i
g
p
p
h
H
2
O
CS
HOCl
ClO
2
H
3
N
CO
2
H
3
N
CO
2
HOCl
Cl
H
3
N
CO
2
fast
O
OH
S
S
S
OH
S
O
O
cysteine sulfinic acid
(CSO
2
H)
cysteic acid
(CSO
3
H)
H
3
N
CO
2
cystine
(CSSC)
Figure 3.17.
Proposed mechanism for the initial reactions between ClO
2
and CSH and
the subsequent decay of the cysteinyl−ClO
2
adduct (adapted from Ison et al. [163] with
the permission of the American Chemical Society).
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