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Effect of sulfuric acid on reactions of peroxymonosulfate ion with sulfides and thiol esters

✍ Scribed by Clifford A. Bunton; Anurag Kumar

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 85 KB
Volume: 11
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(1998110)11:11<803::aid-poc70>3.0.co;2-a

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✦ Synopsis

Peroxymonosulfate ion, HSO 5 À, as Oxone in aqueous H 2 SO 4 , oxidizes sulfides [MeSC 6 H 4 X(p), X = Me, H, NO 2 ] to sulfoxides and converts aryl thiobenzoates [PhCOSC 6 H 4 X(p), X = Me, H] and thiol phosphorus(V) esters [Ph 2 POSPh, (EtO) 2 POSPh, Ph 2 POSEt, Ph(EtO)POSEt] into the acids and sulfonate ions. Second-order rate constants increase with increasing concentration of H 2 SO 4 (10-53 wt%), owing to the high polarity of the medium rather than to acid catalysis. The rate increases fit the Grunwald-Winstein equation based on Y OTs solvent parameters derived from rate effects on S N 1 solvolyses.

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