Affiliations: Department of Environmental Science and Engineering,
POPs Research Center, Tsinghua University, Beijing 100084, China | Department of Chemistry, Tsinghua University, Beijing
100084, China
Abstract: The theoretical linear solvation energy relationship (TLSER)
approach was adopted to predict the aqueous solubility and noctanol/water
partition coefficient of three groups of environmentally important
chemicals-polychlorinated biphenyls (PCBs), polychlorinated dibenzodioxins and
dibenzofurans (PCDDs and PCDFs). For each compound, five quantum parameters
were calculated using AMI semiempirical molecular orbital methods and used as
structure descriptors: average molecular polarizability (α), energy of
the lowest unoccupied molecular orbit (E_{LUMO}), energy of
the highest occupied molecular orbit (E_{HOMO}), the most
positive charge on a hydrogen atom (q_+), and the most
negative atomic partial charge (q_) in the solute molecule.
Then standard independent variables in TLSER equation was extracted and two
series of quantitative equations between these quantum parameters and aqueous
solubility and n-octanolwater partition coefficient were obtained by stepwise
multiple linear regression (MLR) method. The developed equations have both quite
high accuracy and explicit meanings. And the cross-validation test illustrated
the good predictive power and stability of the established models.The results
showed that TLSER could be used as a promising approach in the estimation of
partition and solubility properties ofmacromolecular chemicals, such as
persistent organic pollutants.
