Kinetics and mechanism of ammonolysis and alkaline hydrolysis of naphthyl acetates in aqueous medium: Part II - 6-substituted 2-naphthyl acetates

Several 6-substituted 2-naphthyl acetates have been prepared and kinetics of their ammonolysis and alkaline hydrolysis studied at 20 degrees.25 degrees and 30 degrees C at various pH values in water with 1% dioxan at a definite ionic strength. The ammonolysis is first order in [free ammonia] and the process proceeds through a simple unassisted nucleophilic substitution pathway, which includes the zwitterionic tetrahedral intermediate (T+/-). In no case, is the catalysed pathway visible. The reason for the absence of expected catalysis in the case of ester with methyl substituent is discussed.