Organic sulfur mechanisms. 35. Mechanisms of hydrolysis and related nucleophilic displacement reactions of alkanesulfonyl chlorides: pH dependence and the …

JF King, JYL Lam, S Skonieczny

Index: King; Lam; Skonieczny Journal of the American Chemical Society, 1992 , vol. 114, # 5 p. 1743 - 1749

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Citation Number: 41

Abstract

Abstract: pH-rate profiles, primary kinetic isotope effects, deuterium substitution patterns, and pH-product ratios in the presence of added nucleophiles provide evidence for the following overlapping set of mechanisms for the hydrolysis of methanesulfonyl chloride (1)(in 0.1 M KCl at 25" C):(a) pH I 1-6.7, reaction with water by direct nucleophilic attack on the sulfonyl chloride;(b) pH 1 6.7-11.8, rate-determining attack by hydroxide anion to form sulfene (2), ...