Y. Petit et P. Hutin, MOLECULAR-DYNAMICS OF THE OPENING REACTIO N OF GLYCIDIC ACIDS BY AMMONIA - INFLUENCE OF PROTONATION AND SOLVATION, Bulletin de la Societe chimique de France, 133(11), 1996, pp. 1081-1094
The regioselectivity of the opening reaction of glycidic acids by ammo
nia is justified from semi-empirical orbital calculations associated w
ith molecular dynamics. The reaction takes place only after protonatio
n of the epoxide oxygen atom and solvation by water and ammonia is cru
cial. Steric and coulombic interactions between the carboxylate and th
e reactive ammonia have a major influence on the rationalization of th
e experimental results.