Performance of the SMD and SM8 models for predicting solvation free energy of neutral solutes in methanol, dimethyl sulfoxide and acetonitrile.

Zanith, Caroline; Pliego, Josefredo

The continuum solvation models SMD and SM8 were developed using 2,346 solvation free energy values for 318 neutral molecules in 91 solvents as reference. However, no solvation data of neutral solutes in methanol was used in the parametrization, while only few solvation free energy values of solutes in dimethyl sulfoxide and acetonitrile were used. In this report, we have tested the performance of the models for these important solvents. Taking data from literature, we have generated solvation free energy, enthalpy and entropy values for 37 solutes in methanol, 21 solutes in dimethyl sulfoxide and 19 solutes in acetonitrile. Both SMD and SM8 models have presented a good performance in methanol and acetonitrile, with mean unsigned error equal or less than 0.66 and 0.55 kcal mol in methanol and acetonitrile, respectively. However, the correlation is worse in dimethyl sulfoxide, where the SMD and SM8 methods present mean unsigned error of 1.02 and 0.95 kcal mol, respectively. Our results point out the SMx family of models need be improved for dimethyl sulfoxide solvent.

SOLVATION; FREE energy (Thermodynamics); METHANOL; DIMETHYL sulfoxide; ACETONITRILE; ENTHALPY

Journal of Computer-Aided Molecular Design, 2015, Vol 29, Issue 3, p217

0920-654X

Academic Journal

10.1007/s10822-014-9814-3