title: The aqueous solubility of some herbicidal by-side toxic impurities: predicted data of the 399 chlorinated trans-azoxybenzene congeners.
abstract: The quantitative structure - property relationship (QSPR) and the artificial neural networks (ANNs) methods were used to estimate aqueous solubility (log S and μg/L) of polychlorinated trans-azoxybenzenes (PCt-ABs). These QSPR and ANN models are 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 software and the semi-empirical quantum chemistry method for property parameterization (RM1) in the molecular orbital package (MOPAC) software. The predicted solubility of PCt-AOBs by RM1 and DFT models and depending on a congener varied within a homologue class between 47-19498 and 371-1738 μg/L for Mono-; 33-11481 and 7.9-3630 μg/L for Di-; 6.1-4786 and 4.7-12882 μg/L for Tri-; 1.3-1174 and 0.3-14791 μg/L for Tetra-; 0.4-646 and 0.1-38904 μg/L for Penta-; 0.1-155 and 0.2-63096 μg/L for Hexa-; 0.2-27 and 0.1-646 μg/L for Hepta-; < 0.1-6.2 and 0.8-282 μg/L for Octa-; 0.6-2.6 and 0.8-12 μg/L for NonaCt-AOBs; and 1.2 and 0.5 μg/L for DecaCt-AOB, respectively. Both computational models used were characterized by good predictive abilities and small errors, while calculations by RM1 method were highly competitive compared to a much more time-consuming and expensive method by DFT.
authors.affiliation: Research Group of Environmental Chemistry, Ecotoxicology & Food Toxicology, Institute of Environmental Sciences & Public Health, University of Gdańsk, Gdańsk, Poland.
authors.forename: Sławomir
authors.initials: S
authors.lastname: Piliszek
authors.forename: Agata J
authors.initials: AJ
authors.lastname: Wilczyńska-Piliszek
authors.forename: Jerzy
authors.initials: J
authors.lastname: Falandysz
mesh_terms: D000465:Algorithms; D001391:Azo Compounds / Q000737:chemistry* / Q000633:toxicity; D006540:Herbicides / Q000737:chemistry* / Q000633:toxicity; D015394:Molecular Structure; D016571:Neural Networks, Computer; D021281:Quantitative Structure-Activity Relationship; D012984:Software; D012995:Solubility
chemical_list: D001391:Azo Compounds; D006540:Herbicides; C046115:fenazox