Quantitative structure-property relationships for octanol-air partition coefficients of polychlorinated naphthalenes, chlorobenzenes and p,p'-DDT.
The octanol-air partition coefficient (K(OA)) is a key descriptor of chemicals partitioning between the atmosphere and environmental organic phases. Quantitative structure-property relationships (QSPR) are necessary to model and predict K(OA) from molecular structures. Based on 12 quantum chemical descriptors computed by the PM3 Hamiltonian, using partial least squares (PLS) analysis, a QSPR model for logarithms of K(OA) to base 10 (logK(OA)) for polychlorinated naphthalenes (PCNs), chlorobenzenes and p,p'-DDT was obtained. The cross-validated Q(2)(cum) value of the model is 0.973, indicating a good predictive ability of the model. The main factors governing logK(OA) of the PCNs, chlorobenzenes, and p,p'-DDT are, in order of decreasing importance, molecular size and molecular ability of donating/accepting electrons to participate in intermolecular interactions. The intermolecular dispersive interactions play a leading role in governing logK(OA). The more chlorines in PCN and chlorobenzene molecules, the greater the logK(OA) values. Increasing E(LUMO) (the energy of the lowest unoccupied molecular orbital) of the molecules leads to decreasing logK(OA) values, implying possible intermolecular interactions between the molecules under study and octanol molecules.
Chen
Jingwen
J
School of Environmental Science and Technology, Dalian University of Technology, Zhongshan Road 158-129, 116012, Dalian, People's Republic of China. jwchen@dlut.edu.cn
Xue
Xingya
X
Schramm
Karl-Werner
KW
Quan
Xie
X
Yang
Fenglin
F
Kettrup
Antonius
A