Intramolecular-catalyzed sulfonamide hydrolysis. VII. The Thorpe-Ingold effect in the intramolecular carboxyl-catalyzed hydrolysis of sulfonamides

J Jager, T Graafland, H Schenk, AJ Kirby…

Index: Jager, Jan; Graafland, Teun; Schenk, Henk; Kirby, Anthony J.; Engberts, Jan B. F. N. Journal of the American Chemical Society, 1984 , vol. 106, p. 139 - 143

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Citation Number: 42

Abstract

Abstract: Rate constants and thermodynamic activation parameters have been determined for the intramolecular carboxyl-catalyzed hydrolysis of a series of 1-mono-and 1, l- disubstituted carboxy-N-methyl-N-phenylmethanesulfonamides 1-10. Alkyl and gem-dialkyl substituents favor the formation of the four-membered cyclic transition state. The effect increases with increasing number and size of the alkyl substituents and originates ...