Study of hydrogen bonding in dihydroxyacetone and glyceraldehyde using computational methods

The intramolecular hydrogen bonding in different conformers of dihydroxyacetone (DHA) and its isomer, glyceraldehyde (Gald) was investigated using Density Functional Theory (DFT), second-order Møller-Plesset (MP2) method and “Atoms in Molecules” (AIM) theory. The effect of intramolecular hydrogen bonding on the relative stability of conformers was studied. It was found that the stability of different conformers depends on the size of the ring in which hydrogen bond is formed and the hybridization of the oxygen atom of acceptor. The AIM analysis showed that some of the considered interactions are not real hydrogen bonds and therefore, there is no cooperativity in the considered conformers.