大学化学 >> 2026, Vol. 41 >> Issue (9): 442-448.doi: 10.12461/PKU.DXHX202509012

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NBO分析在研究取代芳烃亲电取代反应区域选择性和活性中的应用

陈玉尧, 邹齐瑞, 刘博文, 李福芸, 张翱, 樊秀微   

  1. 北京印刷学院印刷与包装工程学院, 等离子体物理与材料研究室, 北京 102600
  • 收稿日期:2025-09-06 录用日期:2025-11-06 发布日期:2026-09-01
  • 通讯作者: 樊秀微 E-mail:fanxiuwei@bigc.edu.cn Xiuwei Fan
  • 基金资助:
    北京印刷学院校级重点教学改革项目(20241010)；北京市大学生创新创业训练计划项目(22150725039)

Application of NBO analysis in studying regioselectivity and reactivity of electrophilic aromatic substitution reactions

Yuyao Chen, Qirui Zou, Bowen Liu, Fuyun Li, Ao Zhang, Xiuwei Fan   

  1. The Plasma Physics & Materials Laboratory, School of Printing and Packaging Engineering, Beijing Institute of Graphic Communication, Beijing 102600, China
  • Received:2025-09-06 Accepted:2025-11-06 Published:2026-09-01
  • Contact: Xiuwei Fan E-mail:fanxiuwei@bigc.edu.cn

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摘要： 取代芳烃亲电取代反应的区域选择性传统上依赖取代基电子效应的定性解释，但难以定量解析。本文采用自然键轨道(NBO)分析方法，结合前线分子轨道(FMO)理论，系统研究取代芳烃的电荷分布与反应活性。通过量化典型取代基(活化邻对位基团、钝化邻对位基团、间位定位基团)对苯环电荷转移的影响，揭示了电子再分布的本质规律。研究通过可视化电子效应(NBO电荷差图、静电势图)实现了亲电取代定位规则的定量解析，为有机化学教学提供了直观的计算化学案例，有助于深化学生对芳烃亲电取代反应区域选择性和活性的理解。

关键词: NBO分析, 亲电取代反应, 定位效应, 计算化学教学

Abstract: The regioselectivity of electrophilic aromatic substitution reactions in substituted arenes has traditionally been explained qualitatively through substituent electronic effects, yet quantitative analysis remains challenging. This study employs Natural Bond Orbital (NBO) analysis coupled with Frontier Molecular Orbital (FMO) theory to systematically examine charge distribution and reactivity in substituted arenes. By quantifying the influence of characteristic substituents (activating ortho/para-directing groups, deactivating ortho/para-directing groups, and meta-directing groups) on charge transfer within the aromatic ring, we elucidate the fundamental principles of electronic redistribution. Through visualization of electronic effects (NBO charge difference maps and electrostatic potential maps), we achieve quantitative interpretation of orientation rules in electrophilic aromatic substitution. This work presents a practical computational chemistry case study for organic chemistry education, enhancing students' understanding of regioselectivity and reactivity in aromatic electrophilic substitution reactions.

Key words: NBO analysis, Electrophilic substitution reaction, Orientation effect, Computational chemistry education