Quantitative structure-property relationship of aromatic sulfur-containing carboxylates

摘要

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(M_W), net charges on carboxyl group(Q_(OC)), net charges of nitrogen atoms(Q_N), and the most negative atomic charge (q~-) of the solute molecule. For water solubility (log S_W) and octanol/ water partition coefficient( log K_(OW)), the correction coefficients r_(adj)~2 (adjusted for degrees of freedom) are 0.936 and 0.938, and the standard deviations are 0.364 and 0.223, respectively.