Study of intramolecular hydrogen bonding in ortho-substituted acetanilide compounds using computational methods

摘要

The intramolecular hydrogen bonding formation in ortho-substituted compounds of Acetanilide, ortho-hydroxy Acetanilide and ortho-vitro Acetanilide, was investigated using Density Functional Theory (DFT), Moller-Plesset second-order (MP2) method and "Atoms in Molecules (AIM)" theory. It was found that in each case, the cis isomer is more stable than the trans isomer and ortho-vitro Acetanilide forms a stronger hydrogen bond than ortho-hydroxy Acetanilide. The effects of hydrogen bonding on structural parameters of the considered systems were studied using Becke's functional (B3LYP) and at the ab initio MP2 level in conjunction with different basis sets and suitable structural factors. The results are in agreement with the results of AIM theory.