Vb. Gawandi et al., Role of solute structure on the stability of the OH-adduct of substituted organic sulfides and its transformation to a radical cation, CHEM P LETT, 314(5-6), 1999, pp. 451-458
The sulfur-centered OH-adduct (lambda(max) = 360 nm) of 4-(methylthio)butan
ol transforms (k = 1 X 10(6) s(-1)) to a sulfur-centered dimer radical cati
on (lambda(max) = 485 nm) in basic solution. The rate of transformation is
accelerated in acidic solution and only the dimer radical cation is observe
d at pH = 1. The transformation of the OH-adduct of 3-(methylthio)propanol
is fast even in basic solution and only the intra-molecular radical (lambda
(max) = 410 nm) is observed at pH > 5 and the dimer radical cation (lambda(
max) = 480 nm) at pH = 1. The OH-adduct of 3,3'-thiodipropionamide (lambda(
max) = 350 nm) undergoes transformation (k = 1.4 X 10(5) s(-1)) to an intra
-molecular radical cation (lambda(max) = 370 nm). The formation of the OH-a
dduct and its transformation to a solute radical cation could not be observ
ed with 2-(methylthio)ethanol and 2,2'-thiodiethanamide. (C) 1999 Elsevier
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