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Kinetics and correlation analysis of reactivity in oxidation of organic sulfides by hexamethylenetetramine–bromine
Author(s) -
Choudhary Kirti,
Suri Deepa,
Kothari Seema,
Banerji Kalyan K.
Publication year - 2000
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/1099-1395(200005)13:5<283::aid-poc243>3.0.co;2-o
Subject(s) - hexamethylenetetramine , chemistry , bromine , oxidizing agent , kinetics , sulfide , reactivity (psychology) , alkyl , inorganic chemistry , medicinal chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics
The oxidation of organic sulfides by hexamethylenetetramine–bromine (HABR) to the corresponding sulfoxides is first order with respect to HABR. Michaelis–Menten‐type kinetics were observed with respect to the sulfide. It is proposed that HABR itself is the oxidizing species. Correlation analyses of the rate of the oxidation of 34 sulfides were performed in terms of various single and multiparametric equations. The best correlation was obtained with Charton's LDR and LDRS equations, the polar regression coefficients being negative. The oxidation of alkyl phenyl sulfides exhibited a very good correlation in terms of the Pavelich–Taft equation. A mechanism involving the formation of a halosulfonium cation in the slow step is proposed. Copyright © 2000 John Wiley & Sons, Ltd.