Rapid evaluation of the interaction energies for carbohydrate-containing hydrogen-bonded complexes via the polarizable dipole–dipole interaction model combined with NBO or AM1 charge

Abstract

The polarizable dipole–dipole interaction model, which explicitly involves the permanent dipole–dipole interaction, the van der Waals interaction, the polarization contribution and the covalency interaction, has been proposed in our lab for N–H⋯OC and C–H⋯OC hydrogen-bonded complexes containing amides and peptides. In this paper, the polarizable dipole–dipole interaction model is further developed and applied to hydrogen-bonded complexes containing ribose, deoxyribose, fructose, glucose, maltose and sucrose. We regard the chemical bonds O–H, C–H and C–O in ribose, deoxyribose, fructose, glucose, maltose and sucrose molecules as bond dipoles. The magnitude of the bond dipole moment varies according to its environment. The parameters needed are first determined from the training dimers. The polarizable dipole–dipole interaction model is then applied to a series of carbohydrate-containing hydrogen-bonded complexes. The calculation results show that the polarizable dipole–dipole interaction model not only can produce the equilibrium hydrogen bond distances compared favorably with those produced by the MP2/6-31+G(d,p) method and can produce the interaction energies in good agreement with those yielded by the high quality counterpoised-corrected MP2/aug-cc-pVTZ method, but is much more efficient as well, demonstrating that the polarizable dipole–dipole interaction model and the parameters determined are reasonable and useful.