Neighbouring carboxylate group participation in ester aminolysis in non-hydroxylic solvents. The n-butylaminolysis of aspirin in acetonitrile
Abstract
In acetonitrile the carboxylate group of aspirin anion has been found to assist the n-butylaminolysis of the neighbouring ester function with a mechanism changing from nucleophilic to concomitant nucleophilic and probably general base catalysis as the amine concentration is increased.