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Kinetics and mechanism of oxidation of indole by HSO − 5
Author(s) -
Meenakshisundaram Subbiah,
Sarathi N.
Publication year - 2007
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20215
Subject(s) - chemistry , persulfate , nucleophile , indole test , electrophile , kinetics , reactivity (psychology) , catalysis , polymerization , photochemistry , reaction mechanism , medicinal chemistry , oxygen , organic chemistry , medicine , physics , alternative medicine , polymer , pathology , quantum mechanics
Mechanistic studies on the oxidation of indole [IND] by HSO − 5in aqueous CH 3 CN medium (80:20 v/v) have been carried out, and the reaction is characterized by the rate law −d[HSO − 5 ]/dt = k [IND][HSO − 5 ]HSO − 5and SO 2− 5are probably the respective electrophiles in acidic and basic mediums. Nucleophilic attack of the ethylenic bond on the persulfate oxygen is envisaged to explain the reactivity. The reaction fails to initiate polymerization, and a radical mechanism is ruled out. Thermodynamic parameters very much suggest a bimolecular process. No significant catalytic activity is observed for the reaction system in the presence of Ag + , Cu 2+ , and heteroaromatic N‐bases. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 39: 46–51, 2007