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Kinetic studies on the reactions of 3-isothiazolones with 2-methyl-2-propanethiol

โœ Scribed by John O. Morley; A. Jayne Oliver Kapur; Michael H. Charlton

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
265 KB
Volume
39
Category
Article
ISSN
0538-8066

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โœฆ Synopsis

Abstract

The kinetics of the ringโ€opening reactions of the 3โ€isothiazolones (1aโ€“d) with aqueous 2โ€methylโ€2โ€propanethiol has been explored at pH 4. The results strongly suggest that the reaction is second order in thiol and third order overall. Extrapolation of the kinetic data gives thirdโ€order rate constants that lie in the order (1a) > (1b) > (1c) > (1d) in line with the known biological activity of these derivatives. The mechanism of the reaction is thought to involve attack by one thiol at the sulfur atom of the isothiazolone with the concomitant hydrogen bonding of a second thiol to the amide nitrogen. Calculations of the structure and electronic properties of the isothiazolones at the RHF 6โ€31G** level are supportive. ยฉ 2007 Wiley Periodicals, Inc. Int J Chem Kinet 39: 254โ€“260, 2005

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