Catalysed hydrolysis of an acyl-activated anilide in buffered solutions

Abstract

The hydrolysis of N-(4-nitrophenyl) dichloroacetamide is catalysed by buffer reagents acting as general acids and bases. The dihydrogen phosphate, dihydrogen arsenate, and hydrogen carbonate ions are abnormally effective as general-acid catalysts, and the carbonate ion is probably abnormally effective as a general base. The results of this study do not lend support to the concept of bifunctional catalysis, and are discussed in terms of hypothetical energy–reaction-co-ordinate profiles for proton transfer.