Synthesis and QSPR study on environment-related properties of polychlorinated diphenyl sulfides (PCDPSs)

Twenty-nine congeners of polychlorinated diphenyl sulfide (PCDPS) theoretically possible were synthesized and purified, and their octanol-water partition coefficients (log K-ow) and high performance liquid chromatography capacity factors (HPLC-log k') were determined. Then the constitutional and structural descriptors were obtained respectively to establish 20 models and comparative molecular similarity indices analysis (CoMSIA) method was used to establish 3D models. All the models were robust and predictive, indicating that the electrostatic effect may be the primary factor influencing the two properties of PCDPS. The log K-ow and log k' values of all PCDPS congeners were predicted based on these models. The establishment of linear equation on log K-ow between PCDPS and chlorinated or brominated diphenyl ether (PCDE, PBDE) was attempted, and the hydrophobic differences were considered to relate with the size of the molecules. (C) 2012 Elsevier Ltd. All rights reserved.