基于密度泛函理论计算的多氯联苯毒性的定量结构-性质关系研究

doi:10.6023/A1109302

化学学报 ›› 2012, Vol. 70 ›› Issue (08): 949-960.DOI: 10.6023/A1109302 上一篇下一篇

研究论文

基于密度泛函理论计算的多氯联苯毒性的定量结构-性质关系研究

龙杰义, 易海波, 刘星楷, 汪易非

湖南大学化学化工学院长沙 410082

投稿日期:2011-09-30 修回日期:2011-12-16 发布日期:2012-01-20
通讯作者: 易海波 E-mail:hbyi@hnu.edu.cn
基金资助:
国家自然科学基金委基础科学人才培养基金项目(No. J0830415).

Quantitative Structure-Property Relationship for Polychlorinated Biphenyls: Toxicity and Structure by Density Functional Theory

Long Jieyi, Yi Haibo, Liu Xingkai, Wang Yifei

College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082

Received:2011-09-30 Revised:2011-12-16 Published:2012-01-20
Supported by:
Project suppotted by the National Fundamental Fund Project Subsidy Funds of Personnel Training, National Natural Scicence Fundation of China (No. J0830415).

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摘要/Abstract

多氯联苯(PCBs)是一类人工合成的难降解有机物, 疏水亲油、毒性大, 引起了人们普遍关注. 通过密度泛函理论(DFT)计算获得PCBs 苯环上的负电荷密度(Q)、最低空轨道能量(E_LUMO)、亲电指数(ω)等结构参数, 并分析了PCBs 毒性与其苯环间的共平面性、氯原子取代数(N_Cl)、Q 以及ω 等结构参数之间的关系. 采用SPSS17 统计软件分析了上述结构参数与PCBs 毒性表征量正辛醇-水分配系数(K_OW)的关联度, 并构建lg K_OW 的多元线性回归方程. 采用“交叉检验”方法检验所构建的lg K_OW 定量结构-性质关系(QSPR)方程的稳定性, 并用于预测PCBs 的毒性. 由N_Cl 和ω 构造出的QSPR 方程简单实用、可靠, PCBs 的lg K_OW 计算值与实验结果吻合良好.

关键词: 多氯联苯, 取代数, 亲电指数, 正辛醇-水分配系数, QSPR

Polychlorinated biphenyls (PCBs) with hydrophobicity, lipophilicity and high toxicity, are a group of synthetic persistent organic contaminants, and have caused people widespread concern. In this work, density functional theory (DFT) was employed to calculate some structural parameters of PCBs, such as the negative charge density of the benzene ring (Q), ELUMO, electrophilicity index (ω), and the relationship of toxicity of PCBs with coplanarity, the number of substituted chlorines (N_Cl), Q, and ω was also investigated. Using SPSS17 program, the relevancy of these structural parameters with n-octanol-water partition coefficients (K_OW) was analyzed, and multiple linear regression equations of lg K_OW for PCBs were constructed. Tests of these quantitative structure-property relationship (QSPR) equations were performed to ensure the stability using cross-validation method, and those equations were also used to predict the toxicity of PCBs. The established QSPR equation based on N_Cl and ω is simple and reliable, and the predicted lg K_OW values of PCBs agree well with experimental results.

Key words: PCBs, substituted number, electrophilicity index, n-octanol-water partition coefficient, QSPR

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龙杰义, 易海波, 刘星楷, 汪易非. 基于密度泛函理论计算的多氯联苯毒性的定量结构-性质关系研究[J]. 化学学报, 2012, 70(08): 949-960.

Long Jieyi, Yi Haibo, Liu Xingkai, Wang Yifei. Quantitative Structure-Property Relationship for Polychlorinated Biphenyls: Toxicity and Structure by Density Functional Theory[J]. Acta Chimica Sinica, 2012, 70(08): 949-960.

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基于密度泛函理论计算的多氯联苯毒性的定量结构-性质关系研究

Quantitative Structure-Property Relationship for Polychlorinated Biphenyls: Toxicity and Structure by Density Functional Theory

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