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化学学报
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化学学报 ›› 2010, Vol. 68 ›› Issue (20): 2091-2098. 上一篇    下一篇

研究论文

拓扑量子方法及其在含C＝O和N＝O化合物性能估算中的应用

袁华，曹晨忠*，高硕   

  1. (理论化学与分子模拟教育部重点实验室 分子构效关系湖南省普通高校重点实验室 湖南科技大学化学化工学院 湘潭 411201)
  • 投稿日期:2010-01-03 修回日期:2010-04-19 发布日期:2010-06-23
  • 通讯作者: 袁华 E-mail:yh_cathy@163.com
  • 基金资助:

    国家自然科学基金项目

Topological-quantum Approach and Its Application to the Property Estimation of Compounds Containing Group C＝O or N＝O

YUAN Hua, CAO Chen-Zhong, GAO Shuo   

  1. (Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Key Laboratory of QSAR/QSPR of Hunan Provincial University, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201)
  • Received:2010-01-03 Revised:2010-04-19 Published:2010-06-23

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综合量子化学与拓扑化学知识, 提出了构建Y＝O (Y表示C, N)键拓扑量子键邻接矩阵的方法. 利用该矩阵特征根和量子化学原理, 计算了表征分子轨道能量、原子电荷和键级等的拓扑量子参数. 将这些参数对含C＝O, N＝O基团的有机分子的紫外吸收能量、红外伸缩振动频率和醛酮C＝O上的亲核加成反应速率等性质进行定量结构-性质相关, 得到的模型均具有良好的估算能力.

关键词: 拓扑量子方法, 紫外吸收能量, 红外伸缩振动频率, 亲核加成, 定量结构-性质相关

Integrating the theory of quantum chemistry and topological chemistry, this paper proposed an approach to construct the topological-quantum bond adjacency matrix of Y＝O (Y represents C or N) bond. Based on the eigenvalues of this bond adjacency matrix, three topological-quantum parameters such as molecular orbital energy, atomic charge and bond order were calculated according to quantum chemistry principle. These parameters were correlated to the UV absorption energy, infrared spectroscopy stretching vibration frequency of organic compounds containing C＝O or N＝O group and the nucleophilic addition reaction rate on the site of C＝O in aldehydes and ketones. Good quantitative structure-property relationship models were obtained.

Key words: topological-quantum approach, UV absorption energy, infrared spectroscopy stretching vibration frequency, nucleophilic addition, quantitative structure-property relationship