Electrostatic catalysis and inhibition in aqueous solution. Rate effects on the reactions of charged esters with a cationic steroid bearing an imidazolyl substituent

Abstract

The steroid (1) with a 17β-imidazoyl-and an 11β-ammonio-substituent catalyses the hydrolysis of aryl acetates; esters with an anionic substituent on the phenolic unit show rate enhancements, an ester with a cationic substituent shows a rate retardation, and the rate enhancement for a meta-anionic substituent is much larger than for para-anionic substituents.