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An empirical model for solvation based on surface site interaction points.

Published version
Peer-reviewed

Type

Article

Change log

Authors

Storer, Maria Chiara  ORCID logo  https://orcid.org/0000-0002-3668-1333
Hunter, Christopher A  ORCID logo  https://orcid.org/0000-0002-5182-1859

Abstract

Surface site interaction points (SSIP) provide a quantitative description of the non-covalent interactions a molecule makes with the environment based on specific intermolecular contacts, such as H-bonds. Summation of the free energy of interaction of each SSIP across the surface of a molecule allows calculation of solvation energies and partition coefficients. A rule-based approach to the assignment of SSIPs based on chemical structure has been developed, and a combination of experimental data on the formation of 1 : 1 H-bonded complexes in non-polar solvents and partition of solutes between different solvents was used to parameterise the method. The resulting model is simple to implement using just a spreadsheet and accurately describes the transfer of a wide range of different solutes from water to a wide range of different organic solvents (overall rmsd is 1.4 kJ mol-1 for 1713 data points). The hydrophobic effect as well as the properties of perfluorocarbon solvents are described well by the model, and new descriptors have been determined for range of organic solvents that were not accessible by direct investigation of H-bond formation in non-polar solvents.

Description

Keywords

34 Chemical Sciences, 3406 Physical Chemistry, 3407 Theoretical and Computational Chemistry

Journal Title

Chem Sci

Conference Name

Journal ISSN

2041-6520
2041-6539

Volume Title

12

Publisher

Royal Society of Chemistry (RSC)
Sponsorship
Herchel Smith Fund