摘要: Density functional theory (DFT)-B3LYP level with the 6-311G**(d,p) basis set was used to calculate a set of molecular quantum chemical descriptors of 12 chloroanilines. Quantitative structure-activity relationship (QSAR) models of the bioconcentration factors (B_CF) of the anilines in fish were established using some of the following calculated descriptors: E_HOMO, E_NHOMO, E_LUMO, E_NLUMO, ΔE₁(=E_LUMO-E_HOMO), ΔE₂(=E_NLUMO-E_NHOMO), dipole moment (μ), molecular volume (V), vibrational energy of 0 K (E_v), thermodynamic energy (E), heat capacity (C_v), entropy (S_m) and the charge of benzene ring (Q_ph). Using the variable selection and leaps-and-bounds regression, the quantum chemical descriptors derived directly from the molecular structures were employed to develop a linear QSAR model between the bioconcentration factors (B_CF) and two descriptors (S_m, E_NHOMO) of 12 chloroanilines. Statistically, the most significant one is a two-parameter linear equation with the correlation coefficient (R²) of 0.981 and cross-validated correlation coefficient (R_CV²) of 0.967. The established QSAR model has good stability and predictability based on the results from R_CV² of leave-one-out cross-validation, A_IC, F_IT and t_α/2. The quantum chemical analyses were performed from two aspects of frontier molecular orbital and entropy. The results show that two structural describers are crucial to the bioconcentration activity of chloroanilines.