University Chemistry ›› 2019, Vol. 34 ›› Issue (1): 108-115.doi: 10.3866/PKU.DXHX201805042

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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)

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