Investigations on substituent and solvent effects on solvolysis reactions - Part IX. The influence of polar substituents on the imidazole catalyzed hydrolysis of 2,4-dinitrophenyl acetates in water

The imidazole catalyzed hydrolysis of polar substituted 2,4-dinitrophenyl a cetates in water has been investigated at different temperatures. The obser ved rates correspond to the bimolecular nucleophilic addition of the imidaz ole at the carboxylic carbon atom followed by a very fast hydrolysis of the N-acetylimidazole in water. The influence of polar substituents in the aci d moiety of the ester molecule on the hydrolysis reaction can be described by an electrostatic dipole-dipole interaction in the same way as the neutra l hydrolysis of polar substituted ethyl acetates.