Density functional study of the Hoffmann elimination of (N-Cl),N-methylethanolamine in gas phase and in aqueous solution

Hoffmann elimination involving (N-Cl),N-methylethanolamine and HO− has been theoretically characterized by using DFT at the B3LYP/6-31++G∗∗ level. The role of water as a solvent was analyzed by using both discrete and hybrid discrete-continuum models. The rearrangement proceeds along a water-assisted asynchronous concerted mechanism. Population analysis helps to explain the nature of the chemical rearrangement.