Protonation equilibria of amides and related compounds. Part II. Butyramide, N-butyrylglycine, and some carbamic acid esters

Abstract

Studies of the n.m.r. spectra of solutions of butyramide, N-butyrylglycine, methyl carbamate, ethyl carbamate, ethyl N-methylcarbamate, ethyl NN-dimethylcarbamate, and N-ethoxycarbonylglycine in aqueous sulphuric and aqueous perchloric acids reveal that the protonation behaviour of carbamic acid esters is similar to that of amides, and they are intermediate in basicity between structurally similar amides and esters.