QSPR models for polychlorinated biphenyls: n-Octanol/water partition coefficient

Abstract

The logarithmic n-octanol/water partition coefficient (log K_ow) is an important property for pharmacology, toxicology and medicinal chemistry. Quantitative structure-property relationship (QSPR) model for the lipophilic behaviour (log K_ow) of the data set containing 133 polychlorinated biphenyl (PCB) congeners is analyzed using the conceptual density functional theory based global reactivity parameter such as electrophilicity index (ω) along with energy of lowest unoccupied molecular orbital (E_LUMO) and number of chlorine substituents (N_Cl) as descriptors. A reasonably good coefficient of determination (r² = 0.914) and the internal predictive ability (r²_cv 0.909) values are obtained indicating the significance of the considered descriptors in the property analysis of PCBs. Further, the developed method has widespread applicability from chemical reactivity to toxicity analysis and in studies related to various physicochemical properties in the series of dioxins and other polyaromatic hydrocarbons.