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A Mechanistic Study on the Amidation of Esters Mediated by Sodium Formamide

Author:
Ramirez, Antonio, Mudryk, Boguslaw, Rossano, Lucius, Tummala, Srinivas
Source:
Journal of organic chemistry 2012 v.77 no.1 pp. 775-779
ISSN:
1520-6904
Subject:
chemical reactions, chemical structure, esters, organic chemistry, sodium, solvents
Abstract:
Kinetic and computational studies on the amidation of esters with mixtures of formamide and sodium methoxide are described. Rate studies are consistent with a fast deprotonation of formamide followed by two reversible acyl transfers affected by solvent participation. MP2 calculations suggest that the first acyl transfer between the ester and sodium formamide is rate-determining. The transition structures leading to the formation and collapse of the first tetrahedral intermediate are calculated to be isoenergetic.
Agid:
5498693