title: pKa-dependent formation of amides in water from an acyl phosphate monoester and amines.
abstract: 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 (beta(nuc) approximately 0.9). This provides a simple and quantitative basis for regioselective acylation with these reagents.
authors.affiliation: Lash Miller and Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, ON, Canada.
authors.forename: Jolanta
authors.initials: J
authors.lastname: Wodzinska
authors.forename: Ronald
authors.initials: R
authors.lastname: Kluger
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D004952:Esters; D010710:Phosphates / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D004952:Esters; D010710:Phosphates; D014867:Water