Octanol-water partition coefficient from 3D-RISM-KH molecular theory of solvation with partial molar volume correction

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DOIResolve DOI: http://doi.org/10.1021/acs.jpcb.5b01291
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TypeArticle
Journal titleJournal of Physical Chemistry B
ISSN1520-6106
Volume119
Issue17
Pages55885597; # of pages: 10
SubjectChemical compounds; Functional groups; Molecular dynamics; Solvation; Solvents; Volume measurement; Chemical characteristic; Explicit solvent molecular dynamics; Hydration free energies; Hydrophobic/hydrophilic; Molecular theory of solvation; Octanol-water partition coefficient; Partition coefficient; Solvation free energies; Free energy
AbstractThe 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.; 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.
Publication date
PublisherACS Publications
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); National Institute for Nanotechnology
Peer reviewedYes
NPARC number21275841
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Record identifier8930d8d9-ff98-4b65-903a-a5896a1b4000
Record created2015-07-14
Record modified2016-05-09
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