Issue 4, 1979

The kinetics and mechanism of the mercurous ion-promoted hydrolysis of S-thio esters

Abstract

The kinetics of the mercurous ion-promoted hydrolysis of three p-substituted S-ethyl thiobenzoates have been studied. It has been established that the mercurous ion is a powerful soft acid with a strength lying between those of the mercuric and silver ions. The sequence of ester reactivity is p-MeO > p-H [double greater-than, compressed]p-NO2. The substituent effects, the values of the activation parameters, and the effects of pH changes all suggest that for the p-NO2 derivative the hydrolysis mechanism is AAc2, but that for the other two esters the mechanism is AAc1.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1979, 458-461

The kinetics and mechanism of the mercurous ion-promoted hydrolysis of S-thio esters

G. Patel and R. S. Satchell, J. Chem. Soc., Perkin Trans. 2, 1979, 458 DOI: 10.1039/P29790000458

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