48000-95-9Relevant articles and documents
pKa-dependent formation of amides in water from an acyl phosphate monoester and amines
Wodzinska, Jolanta,Kluger, Ronald
, p. 4753 - 4754 (2008/09/21)
(Chemical Equation Presented) Acyl phosphate monoesters are readily prepared biomimetically activated anionic derivatives of carboxylic acids that react rapidly with amines in water to form amides. A plot of the logarithms of the rate constants for the reactions of a series of primary amines with benzoyl methyl phosphate depends on the pKa of the conjugate acids of the amines (βnuc ≈ 0.9). This provides a simple and quantitative basis for regioselective acylation with these reagents.