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

Abstract

Twenty-nine congeners of polychlorinated diphenyl sulfide (PCDPS) theoretically possible were synthesized and purified, and their octanol-water partition coefficients (logK(ow)) and high performance liquid chromatography capacity factors (HPLC-logk') were determined. Then the constitutional and structural descriptors were obtained respectively to establish 2D 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 logK(ow) and logk' values of all PCDPS congeners were predicted based on these models. The establishment of linear equation on logK(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.