Assessment of long-range transport potential of polychlorinated Naphthalenes based on three-dimensional QSAR models

Abstract

Experimentally determined octanol–air partition coefficients (K _OA) for 43 polychlorinated naphthalene (PCN) congeners and experimentally determined subcooled liquid vapor pressures (P _L) for 17 PCN congeners were used with comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) to generate three-dimensional quantitative structure–activity relationship (3D–QSAR) models. The data were used to predict K _OA values for the other 32 congeners and P _L values for the other 58 congeners. The CoMFA and CoMSIA model contour maps showed that the electrostatic fields of the PCN molecules are the most important factors affecting the K _OA and P _L values. The long-range transport potentials of several PCN homologs were assessed using the following grading system: high mobility (MoCNs), relatively high mobility (DiCNs to TeCNs), relatively low mobility (PeCNs to HeCNs) and low mobility (HeCNs and OCN). The PCN-2 molecule was modified using the contour maps of the two models, and the results showed that introducing an electronegative R₁ substituent increased the K _OA value but introducing an electropositive R₆ substituent decreased the P _L value. PCN-2 was in the high mobility class, but introducing these substituents moved the long-range transport potentials of the modified molecules to the relatively high mobility class.

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