QSPR modeling of the logiC_(ow) and logiC_(oc) of polymethoxylated, polyhydroxylated diphenyl ethers and methoxylated-, hydroxylated-polychlorinated diphenyl ethers

摘要

In the present study, the structural parameters of 209 types of polymethoxylated diphenyl ethers (PMeODEs), 209 types of polyhydroxylated diphenyl ethers (PHODEs), seven types of methoxylated-polychlorinated diphenyl ethers (MeO-PCDEs) and seven types of hydroxylated-polychlorinated diphenyl ethers (HO-PCDEs) were calculated using the Gaussian 09 program at the B3LYP/6-311G(star star) level. Using structural and positional parameters as descriptors, quantitative structure-property relationships (QSPR) models for the prediction of n-octanol/water partition coefficient (logK(ow)) and soil sorption coefficient normalized to organic carbon (logK(oc)) were established and verified. The position parameters N-2(6), N-3(5) and N-4 were the main positional factors influencing logK(ow) and logK(oc) of PMeODEs and PHODEs. The molecular polarizability alpha was entered into the QSPR models of the logK(ow) and logK(oc) of PMeODEs, PHODEs and MeO/HO-PCDEs, indicating that the molecular volume could influence the two environment-related properties of DEs significantly. All of the established QSPR models showed good goodness-of-fit, robustness, and predictive ability. The two models for all of the tested DEs are slightly inferior compared with the models for only a class of compounds. In addition, application domain analysis indicated that the models reliably predicted the logK(ow) and logK(oc) of the mon- to hexa-DEs.