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Title: Oxidation of substituted phenyl methyl sulphides by N-chloroacetamide in acidic medium: A kinetic and mechanistic study
Authors: Perumal, S
Ganesan, M
Issue Date: Nov-1989
Publisher: NISCAIR-CSIR, India
Abstract: The kinetics of oxidation of several substituted phenyl methyl sulphides by Nschloroacetamide (NCA) yielding sulphoxides have been studied in acidic aqueous acetonitrile medium. The reaction displays first-order dependence each in [sulphide], [NCA]and [H+]. The reaction rate is not influenced by the addition of acetamide, mercuric acetate &I1dacrylamide. Presence of electron releasing substituents in the phenyl ring enhances the rate while that of opposite ones retards it. A good Hammett correlation between the rate data and a constants is obtained with a ρ-value of - 3.29 at 313K (r = 0.999). The results point to a polar mechanism involvingthe rate-limiting formation of a chlorosulphonium cation by the electrophilic attack of a protonated NCA on the sulphide sulphur. The chlorosulphonium cation presumably hydrolyses to sulphoxide in a fast step.
Page(s): 961-964
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.28A(11) [November 1989]

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