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Oxidation of organic sulfides by peroxyl radicals; search for an adduct intermediate

Bonifacic M., Stefanic I.

Nukleonika

2000

Vol. 45, nr 1

39-44

The reaction mechanism of dimethyl sulfide oxidation by peroxyl radicals (CCl3OOź and CHCl2OOź) in aqueous/alcohol solutions has been studied by means of pulse radiolysis with optical detection in order to gain evidence for the formation of an adduct intermediate, ROO-źS(CH3)2. In the range of 300-650 nm, the only absorbing product was the one-electron oxidized species [(CH3)2S\S(CH3)2]+, and no indication of an additional absorption attributable to an adduct precursor was found. Under the condition of only 50% conversion of CHCl2OOź into the sulfide radical cation, however, addition of a small amount of I- resulted in formation of (CH3)2S\I as the only product and at a yield equal to that of CHCl2OOź radicals. This result is explained by the reaction of iodide ions with a precursor of [(CH3)2S\S(CH3)2]+ species, namely, the adduct CHCl2OO-źS(CH3)2 and is, thus, taken as conclusive, although indirect, evidence of the existence of this adduct intermediate.