Affiliations: State Key Laboratory of Environmental Simulation and Pollution Control, Institute of Environmental Sciences, Beijing Normal University, Beijing 100875, China | School of the Environment, Nanjing University, Nanjing 210093, China
Abstract: Based on quantum chemical calculations, TLSER model (theoretical linear solvation energy relationships) and atomic charge approach were applied to model the partition properties (water solubility and octanol/water partition coefficient) of 96 aromatic sulfur-containing carboxylates, including phenylthio, phenylsulfinyl and phenylsulfonyl carboxylates. In comparison with TLSER models, the atomic charge models are more accurate and reliable to predict the partition properties of the kind of compounds. For the atomic charge models, the molecular descriptors are molecular surface area (S), molecular shape (O), weight (MW), net charges on carboxyl group (QOC), net charges of nitrogen atoms (QN), and the most negative atomic charge (q−) of the solute molecule. For water solubility (log SW) and octanol/water partition coefficient (log KOW), the correction coefficients r2adj (adjusted for degrees of freedom) are 0.936 and 0.938, and the standard deviations are 0.364 and 0.223, respectively.
Keywords: octanol/water partition coefficient, water solubility, atomic charge model, TLSER, quantum chemical descriptor