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Three-dimensional quantitative structure property relationship(3D-QSPR) on aqueous solubility(-lgS_w) and n-octanol/water partition coefficient(lgK_ow) of halogeno-benzene

摘要：对卤代苯化合物的水溶解度(-lgS_w)和正辛醇/水分配系数(lgK_ow)分别进行了基于三维结构的比较分子场(CoMFA)和比较分子相似性指数(CoMSIA)分析,建立了三维定量结构-性质相关(3D-QSPR)模型,并将所获结果与密度泛函理论(DFT)方法得到的2D-QSPR模型进行了比较.结果表明:-lgS_w的CoMFA和CoMSIA模型交叉验证相关系数Q²分别为0.902和0.940,决定系数R²分别为0.982和0.986,模型稳定性和估算能力较好;lgK_ow的CoMFA和CoMSIA模型Q²分别为0.926和0.988,R²分别为0.983和0.997;本研究所建的3D-QSPR模型的估算能力优于2D-QSPR模型;CoMFA和CoMSIA模型三维等势图表明,取代基的疏水效应对该类化合物的水溶解性能及正辛醇/水分配系数的影响更为显著, 立体效应次之,静电场效应影响较小.

Abstract：The aqueous solubility(-lgS_w) and n-octanol/water partition coefficient(lgK_ow) of halogeno-benzene were studied using comparative molecular field analysis(CoMFA) and comparative molecular similarity index analysis(CoMSIA). Corresponding three-dimensional quantitative structure property relationship(3D-QSPR) models were obtained. In addition, the 3D-QSPR models were compared with the 2D-QSPR model that optimized by density function theory (DFT). The results suggested that: 1The cross-validation correlation coefficient(Q²) and non-cross-validation correlation coefficient(R²) of -lgS_w for CoMFA model and CoMSIA model were 0.902 and 0.982, and 0.940 and 0.986, respectively, which indicated that the CoMFA and CoMSIA models had good stability and good predicted ability. 2 The Q² and R² of CoMFA models and CoMSIA model of logK_ow were 0.926 and 0.983, and 0.988 and 0.997 respectively, suggesting the established model had good stability and predictive ability. 3 The predictive ability of established 3D-QSPR models for -lgS_w and logK_ow were better than that of their corresponding 2D-QSPR models. 4 In addition, contour map indicated that the hydrophobic factor had the biggest influence on -lgS_w and lgK_ow, followed by the steric factor and the electrostatic factor.

Key words：halogeno-benzene comparative molecular field analysis comparative molecular similarity index analysis density function theory