Steric effects in the nucleophilic versus general base-catalysed intramolecular carboxy-group-assisted solvolysis of esters
Abstract
Intramolecular participation by carboxylate anion in the solvolysis of the hindered ester 2-carboxyphenyl mesitoate in anhydrous methanol, occurs entirely by a nucleophilic mechanism in contrast to aspirin which previously has been shown to involve the kinetically equivalent general base mechanism.