大学化学 >> 2019, Vol. 34 >> Issue (1): 108-115.doi: 10.3866/PKU.DXHX201805042

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单取代苯环定位效应定量分析和图形可视化解释

李强根*(),李宣映,毛双   

  • 收稿日期:2018-05-24 发布日期:2019-01-16
  • 通讯作者: 李强根 E-mail:liqianggen@hotmail.com
  • 基金资助:
    四川省教育厅项目(18ZB0481)

Quantitative Analysis and Graphical Visualization Interpretation of Mono-substituted Benzene Ring Localization Effect

Qianggen LI*(),Xuanying LI,Shuang MAO   

  • Received:2018-05-24 Published:2019-01-16
  • Contact: Qianggen LI E-mail:liqianggen@hotmail.com
  • Supported by:
    四川省教育厅项目(18ZB0481)

摘要:

目前对于苯环上亲电取代反应定位规律的解释基本上都停留在基于实验的定性层面。本文以5个典型的单取代苯分子(苯胺、甲苯、氯苯、硝基苯和苯甲醛)为代表,采用多种量子化学方法(静电势、原子电荷、前线分子轨道理论、福井函数及双描述符等),对它们的亲电取代反应位点进行了研究。通过定量的数据和直观的图形,揭示苯分子亲电取代反应定位规律的本质,弥补了教材与教学中存在的不足,研究结果可以为大学《有机化学》教材的编写和课程教学提供有用的参考。

关键词: 亲电取代反应, 定位效应, 量化计算, 图形可视化分析

Abstract:

Currently, the interpretation of the location effect of electrophilic substitution reaction on benzene ring is mainly based on the qualitative explanation of the experiment. In this paper, we chose five typical mono-substituted benzene molecules (including aniline, toluene, chlorobenzene, nitrobenzene, benzaldehyde) as the representative, and carried out a study on the electrophilic substitution reaction sites of those molecules by quantum chemical methods (including electrostatic potential, atomic charges, frontier molecular orbital theory, Fukui function and dual descriptor, etc.). Through quantitative data and visual graphics, this paper reveals the nature of the orientation of benzene molecular electrophilic substitution reaction, and makes up for the shortcomings in teaching and teaching materials. The results of this study can provide useful reference for the compilation of the organic chemistry textbook and teaching of the organic chemistry course.

Key words: Electrophilic substitution reaction, Localization effect, Quantitative calculation, Graphic visualization analysis

MSC2000: 

  • G64