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 Kow) and high performance liquid chromatography capacity factors (HPLC-log k′) 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 log Kow and log k′ values of all PCDPS congeners were predicted based on these models. The establishment of linear equation on log Kow 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.

► Some PCDPS congeners were synthesized and the log Kow and log k′ were determined. ► Three methods were used to establish models for predicting log Kow and log k′. ► The log Kow and log k′ of all PCDPS congeners were predicted based on the models. ► The electrostatic effect may be the primary factor influencing log Kow and log k′. ► The log Kow differences between PCDPS and PCDE, PBDE relate to the molecule size.