Solvation of chromone using combined Discrete/SCRF models

Abstract

The solvation of chromone has been investigated using three different combined Discrete/SCRF models. Four chromone–H 2O complexes and one chromone–4H 2O complex were obtained from geometry optimizations at the HF/6-31G(d) level. Three SCRF methods (PCM/6-31G(d), PCM/AM1 and SM2/AM1) were applied to such complexes in order to: (1) evaluate the reliability of the combined Discrete/SCRF models; (2) investigate the effects of the explicit water molecules on the free energy of solvation; and (3) analyze the characteristics of the different solvation sites of chromone. The results show that explicit solvent molecules exert a large influence on the free energy of solvation of a given molecular system providing some information about the solvation sites. Thus, the interaction of the carbonyl oxygen of chromone with the explicit water molecules is stronger than interaction provided by the ether oxygen, providing the complexes with the former interaction a more hydrophobic free energy of solvation than those with the latter. On the other hand, the comparison of the free energies of solvation for solutes with explicit water molecules in the first hydration shell and the free energies of solvation of the molecular system computed in an all-continuum approach reveals that the combined Discrete/SCRF models constitute a very reasonable strategy.