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Title: Kinetics and mechanism of the oxidation of organic sulphides by quinolinium bromochromate
Authors: Dhariwal, Varsha
Yajurvedi, Deeksha
Sharma, Pradeep K
Issue Date: May-2006
Publisher: NISCAIR-CSIR, India
IPC Code: Int. Cl.8 C07B33/00
Abstract: The oxidation of thirty-four sulphides by quinolinium bromochromatc (QBC) has been found to result in the formation of the corresponding sulphoxides. The reaction is first order with respect to both QBC and the sulphide. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form: kobs = a + b [H+]. The oxidation has been studied in 19 different organic solvents. An analysis of the solvent effect by Swain's equation shows that both the cation- and anion-solvating powers of the solvents play an important role in the oxidation. The rates of oxidation meta - and para-substituted phen yl methyl sulphides have been correlated with Charton's LDR equation. The rates of the ortho-compounds show excellent correlation with the LDRS equation. The oxidation of alkyl phenyl sulphides is subject to both polar and steric effects of the alkyl groups. The polar reaction constants are negative indicating an electro n-deficient sulphur centre in the slow step. A mechanism involving formation of a sulfurane intermediate in the slow step has also been proposed.
Page(s): 1158-1164
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections: IJC-A Vol.45A(05) [May 2006]

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