Rapid evaluation of the interaction energies for O–H···O hydrogen-bonded complexes

Abstract

Rapid and accurate evaluation of the O–H···O interaction energies is important because the O–H···O hydrogen bonds are ubiquitous in biosystems. In this paper, the polarizable dipole–dipole interaction model is applied to O–H···O hydrogen-bonded complexes containing water, N-methylacetamide, methanol, ribose, deoxyribose, glucose, etc., to estimate the hydrogen bond structures and the interaction energies. We regard the chemical bonds O–H, N–H, C–H, C=O and C–O in water, N-methylacetamide, methanol, ribose, deoxyribose and glucose molecules as bond dipoles. The magnitude of the bond dipole moment varies according to its environment. Six O–H···O hydrogen-bonded dimers are first chosen as training dimers to determine the parameters needed. Then, the polarizable dipole–dipole interaction model together with the parameters determined is applied to a series of complexes where the binding is dominated by O–H···O interaction. The calculation results show that the polarizable dipole–dipole interaction model produces the hydrogen bond structures compared favorably with those produced by the MP2/6-31 + G(d,p) method and produces the interaction energies in good agreement with those yielded by the high-quality counterpoise-corrected MP2/aug-cc-pVTZ method, suggesting that the polarizable dipole–dipole interaction model and the parameters determined in this work are reasonable. Based on the calculation results obtained, the nature of the O–H···O interactions in these complexes are further discussed.