Journal
JOURNAL OF PHYSICAL CHEMISTRY B
Volume 119, Issue 17, Pages 5588-5597Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jpcb.5b01291
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Funding
- Alberta Prion Research Institute, APRI [201300009, 201300023]
- University of Alberta
- National Institute for Nanotechnology
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The octanol-water partition coefficient is an important physical-chemical characteristic widely used to describe hydrophobic/hydrophilic properties of chemical compounds. The partition coefficient is related to the transfer free energy of a compound from water to octanol. Here, we introduce a new protocol for prediction of the partition coefficient based on the statistical-mechanical, 3D-RISM-KH Molecular theory of solvation. It was shown recently that with the compound-solvent correlation functions obtained from the 3D-RISM-KH molecular theory of solvation, the free energy-functional supplemented with the correction linearly related to the partial molar volume obtained from the Kirkwood-Buff/3D-RISM theory, also called the universal correction (UC), provides accurate prediction of the hydration free energy of small compounds, compared to explicit solvent molecular dynamics [Palmer, D. S.; et al. J. Phys.: Condens. Matter 2010, 22, 492101]. Here we report that with the UC reparametrized accordingly this theory also provides an excellent agreement with the experimental data for the solvation free energy in nonpolar solvent (1-octanol) and so accurately predicts the octanol-water partition coefficient. The performance of the Kovalenko-Hirata (KH) and Gaussian fluctuation (GF) functionals of the solvation free energy, with and without UC, is tested on a large library of small compounds with diverse functional groups. The best agreement with the experimental data for octanol-water partition coefficients is obtained with the KH-UC solvation free energy functional.
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