物理化学学报 >> 2002, Vol. 18 >> Issue (07): 600-603.doi: 10.3866/PKU.WHXB20020706

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结合三维静电势参数研究二取代苯的定量结构－疏水性关系

赵文娜;邹建卫;商志才;郭明;俞庆森   

  1. 浙江大学化学系,杭州　310027
  • 收稿日期:2001-11-22 修回日期:2002-01-21 发布日期:2002-07-15
  • 通讯作者: 邹建卫 E-mail:jwzou@css.zju.edu.cn

A QSPR Study on n-Octanol/Water Partition Coefficient of Disubstituted Benzenes:Application of Theoretical Descriptors Derived from Electrostatic Potentials

Zhao Wen-Na;Zou Jian-Wei;Shang Zhi-Cai;Guo Ming;Yu Qing-Sen   

  1. Department of Chemistry,Zhejiang University,Hangzhou　310027
  • Received:2001-11-22 Revised:2002-01-21 Published:2002-07-15
  • Contact: Zou Jian-Wei E-mail:jwzou@css.zju.edu.cn

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摘要： 对含有常见取代基的92个二取代苯化合物进行了结构优化和静电势及其导出参数的计算,运用多元线性回归方法对化合物的疏水常数与分子的结构参数进行了关联.结果表明,分子表面负静电势的加和ΣV－S、分子空间内最负的静电势Vmin、表面最大静电势Vs,max以及分子体积V、极性表面积APS和分子的偶极密度μ/V这六个参数,可以很好地用于表达这些化合物疏水性与分子结构间的定量关系,而不用具体考虑分子中极性基团间的相互作用.用建立起来的QSPR(quantitative structure-property relationship)关系式对111个类似化合物的疏水性进行了预测,获得了满意的结果.

关键词: 疏水常数, 定量结构－性质关系, 分子静电势, 从头算

Abstract: Geometrical optimization and electrostatic potential calculations have been performed at HF/6-31G level for 92 disubstituted benzene molecules. Linear correlation between the n-octanol /water partition coefficient and the theoretical descriptors of molecular structure has been established by multiple regression method. It appears that Σ,Vmin,Vs,max,V,APS and μ/V could be well used to express the quantitative structure － hydrophilic relationships of the 92 molecules. A test set containing 111 molecules was used to investigate the predictive ability of the QSPR. The result is satisfing.

Key words: Partition coefficient, QSPR(quantitative structure-property relationship), Molecular electrostatic potential, Ab initio