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|Title:||Oxidation of substituted phenyl methyl sulphides by N-chloroacetamide in acidic medium: A kinetic and mechanistic study|
|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.|
|Appears in Collections:||IJC-A Vol.28A(11) [November 1989]|
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