Estimation of the intramolecular O-H···O═C hydrogen bond energy via the molecular tailoring approach. Part I: aliphatic structures.

A simple and universal method for the estimation of the intramolecular hydrogen bond (HB) energy (E(HB)) in hydroxycarbonyl aliphatic compounds is proposed by the application of the molecular tailoring approach (MTA) based on calculations at the second-order Møller-Plesset MP2 level. The calculation of EHB can be realized by the one optimization and three single point calculations of the energy for each compound with carbonyl and hydroxyl groups involved in HB. The intramolecular hydrogen bond energies estimated for 153 structures (of 102 compounds) ranged from 1.