Molecular dynamics of the opening reaction of glycidic acids by ammonia. Influence of protonation and solvation.

The regioselectivity of the opening reaction of glycidic acids by ammonia is justified from semi-empirical orbital calculations associated with molecular dynamics. The reaction takes place only after protonation of the epoxide oxygen atom and solvation by water and ammonia is crucial. Steric and coulombic interactions between the carboxylate and the reactive ammonia have a major influence on the rationalization of the experimental results.