RECENT PERSPECTIVES CONCERNING THE MECHANISM OF H3O+-PROMOTED AND OH--PROMOTED AMIDE HYDROLYSIS

The amidic unit is of fundamental importance in biological systems and to organic chemistry. Of primary concern to living systems are the acyl-transfer reactions of amides, not the least of which is the transfer to H2O, or hydrolysis. In spite of the intense effort that has <formula oriented> been devoted to the enzyme-promoted hydrolysis of amides (peptides), it comes somewhat as a surprise that the nonenzymatic hydrolytic processes were, up until recently, rather ill-defined. 1 The historical reasons for this, no doubt, stem not from lack of interest nor importance, but from the slowness of the reactions for unactivated, or “normal”, amides brought about by the inherent stability of the N-C(O) linkage that hampers the study under all but the most extreme conditions of pH and temperature. © 1992, American Chemical Society. All rights reserved.