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Quantum chemical approach to estimate physicochemical compound properties: Application to substituted benzenes
Author(s) -
Schüürmann Gerrit
Publication year - 1995
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620141209
Subject(s) - solvation , thermodynamics , partition coefficient , chemistry , vapor pressure , quantitative structure–activity relationship , intermolecular force , quantum chemical , solubility , computational chemistry , molecule , organic chemistry , physics , stereochemistry
Estimation models for Henry's law constant ( H ), water solubility ( S w ), vapor pressure ( P v ), and octanol/water partition coefficient ( K ow ) of nonelectrolytes are derived from basic thermodynamic equations. The resultant regression equations require only two molecular descriptors, which are available from chemical structure through semiempirical quantum chemical calculations: free energy of solvation (δ G s ), and molecular contact surface area (CSA). Results are presented for a set of 17 benzenes with experimental data taken from literature, yielding squared correlation coefficients r 2 adj (adjusted for degrees of freedom) between 0.83 and 0.95. The discussion includes limitations from currently available continuum solvation models to calculate δ G s , aspects of potential error compensation, and the suitability of this approach to understand macroscopic compound properties in terms of calculated quantities that represent distinct types of intermolecular interactions.