MOLECULAR-DYNAMICS OF THE OPENING REACTIO N OF GLYCIDIC ACIDS BY AMMONIA - INFLUENCE OF PROTONATION AND SOLVATION

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.