大学化学 >> 2021, Vol. 36 >> Issue (6): 2007019.doi: 10.3866/PKU.DXHX202007019

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双取代苯的亲电取代反应区域选择性规则的理论解释和实验依据

王佳怡, 许家喜()   

  • 收稿日期:2020-07-07 录用日期:2020-08-19 发布日期:2020-09-15
  • 通讯作者: 许家喜 E-mail:jxxu@mail.buct.edu.cn
  • 作者简介:许家喜, Email: jxxu@mail.buct.edu.cn
  • 基金资助:
    《有机化学》和《中级有机化学》一流课程建设项目

Theoretical Rationale and Experimental Evidences on Regioselective Rule in Aromatic Electrophilic Substitution of Disubstituted Benzenes

Jiayi Wang, Jiaxi Xu()   

  • Received:2020-07-07 Accepted:2020-08-19 Published:2020-09-15
  • Contact: Jiaxi Xu E-mail:jxxu@mail.buct.edu.cn

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摘要：

芳香化合物的亲电取代反应是合成不同取代芳香化合物的重要方法，芳香亲电取代反应的区域选择性规则是实现控制合成所需目标分子的理论依据。本文从中间体稳定性、反应活化能和相对反应速率的角度讨论了双取代苯的芳香亲电取代反应区域选择性规则的理论解释和实验依据，为学生正确理解该选择性规则提供了合理的解释和实验证据。

关键词: 芳香亲电取代, 区域选择性, 双取代苯, 活化能, 相对速率

Abstract:

Aromatic electrophilic substitution is a very important method to synthesize different substituted arenes. Its regioselective rule is the theoretical evidence to realize the controlled synthesis of the desired target molecules. Theoretical rationale and experimental evidences on the regioselective rule in the aromatic electrophilic substitution of disubstituted benzenes are discussed here from the viewpoints of stabilities of intermediates, activation energies, and relative reaction rates. It would provide reasonable explanation and experimental evidence for the regioselective rule and is convenient for students to understand correctly.

Key words: Aromatic electrophilic substitution, Regioselectivity, Disubstituted benzene, Activation energy, Relative rate