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KMID : 1059519940380060442
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Journal of the Korean Chemical Society
1994 Volume.38 No. 6 p.442 ~ p.448
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Kinetics and Mechanism of Nucleophilic Addition of Sodium Thiophenoxide to α-(n-Butyl)-N-Phenylnitrone Derivatives
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Lee Kwang-Il
Lee Suck-Woo
Kwak Chun-Geun
Kim Young-Ju
Rho Seung-Il
Lee Gi-Chang
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Abstract
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The rate constants of the nucleophilic reaction of α-(n-butyl)-N-phenylnitrone and its derivatives have been determined by ultraviolet spectrophotometry at 25℃ and a rate equation which can be applied over a wide pH range was obtained. Final product of the addition reaction was α-phenylthiobutylidene-aniline. Base on the rate equation, genernal base effect, substituent effect and final product, plausible mechanism of addition reaction have been proposed. Below pH 3.0 the reaction was inititated by the addition of thiophenol, and in the range of pH 3.0∼10.0, proceeded by the competitive addition of thiophenol and thiophenoxide anion. Above the pH 10.0, the reaction proceeded through the addition of a thiophenoxide anion.
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