QSAR and ANN for the estimation of water solubility of 209 polychlorinated trans-azobenzenes

Abstract

Polychlorinated trans-azobenzenes (PCt-ABs) are less studied a highly toxic impurity in 2,3-dichloroaniline (2,3-D) and some herbicides and are compounds of environmental relevance lacking experimental physical and chemical properties data. In this study, to fulfill gaps on environmentally relevant partitioning properties of PCABs, the values of water solubility (μg/L and log S) have been determined for 209 congeners of chloro-trans-azobenzene (Ct-AB) by means of quantitative structure - property relationship (QSPR) approach and artificial neural networks (ANN) predictive ability. The quantitative structure - property relationship (QSPR) approach used based on geometry optimalization and quantum-chemical structural descriptors, which were computed on the level of density functional theory (DFT) using B3LYP functional and 6-311++G** basis set in Gaussian 03 and the semi-empirical quantum chemistry method for property parameterization (PM6) in the molecular orbital package (MOPAC) software. The predicted solubility of PCt-ABs by PM6 and DFT models and depending on a congener within a homologue class varied between 1995-11481 and 5370-15135 μg/L for mono-; 170-5495 and 138-9332 μg/L for di-; 36-1950 and 209-5248 μg/L for tri-; 15-794 and 41-3715 μg/L for tetra-; 5.5-209 and 39-1259 μg/L for penta-; 1.8-98 and 3.5-1096 μg/L for hexa-; 1.5-34 and 4.7-214 μg/L for hepta-; 0.71-6.2 and 0.76–26 μg/L for octa-; 0.83-1.7 and 0.69-1.2 μg/L for nonaCt-ABs; and between 0.36 and 0.04 μg/L for decaCt-AB, respectively. The calculations by PM6 were highly efficient and inexpensive compared to these by DFT, while both models gave data of similar accuracy.

Keywords:

• Polychlorinated azobenzenes
• PCt-ABs
• herbicides
• POPs
• water solubility
• environmental fate

Acknowledgments

The DFT computations were carried out using the computers in the TASK - Academic Computer Center in Gdańsk. A partial financial support by the Ministry of Science and Higher Education under grant DS/8250-4-0092-11 is acknowledged.