QSPR models for the physicochemical properties of halogenated methyl-phenyl ethers

Abstract

Halogenated methyl-phenyl ethers (anisoles) are ubiquitous organic compounds in the environment. In the present study, geometrical optimization and electrostatic potential calculations have been performed for 134 halogenated anisoles at the HF/6-31G* level of theory. A number of statistically based parameters have been obtained. Linear relationships between sub-cooled liquid vapor pressures (lg p L), n-octanol/water partition coefficient (lg K ow) and aqueous solubilities (−lg S w,L) of halogenated anisoles and the structural descriptors have been established by multiple regression method. The result shows that the quantities derived from electrostatic potential V min, V s,max, ∑ V s + , ∑ V s − , V s,av − and ν, together with the molecular volume ( V mc) and E HOMO can be well used to express the quantitative structure–property relationships of halogenated anisoles, which proves the general applicability of this parameter set to a great extent. Good predictive capabilities have also been demonstrated. Based on these excellent equations, the predicted values have been presented for those halogenated anisoles whose experimentally determined physicochemical properties are unavailable.