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Citation: Yuyao Chen, Qirui Zou, Bowen Liu, Fuyun Li, Ao Zhang, Xiuwei Fan. 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[J]. University Chemistry, ;2026, 41(9): 442-448. doi: 10.12461/PKU.DXHX202509012 shu

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

The Plasma Physics & Materials Laboratory, School of Printing and Packaging Engineering, Beijing Institute of Graphic Communication, Beijing 102600, China

Corresponding author: Xiuwei Fan, fanxiuwei@bigc.edu.cn
Received Date: 6 September 2025
Revised Date: 6 November 2025

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。
- NBO analysis,
- Electrophilic substitution reaction,
- Orientation effect,
- Computational chemistry education
1. [1]
2. [2]
3. [3]
  O.A. Stasyuk, H. Szatylowicz, T.M. Krygowski, C. Fonseca Guerra, Phys. Chem. Chem. Phys. 2016, 18, 11624
4. [4]
  A. Jezuita, H. Szatylowicz, T. Krygowski, Chem. Phys. Lett. 2020, 753, 13567.
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, JR. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, et al., Gaussian 09, Revision C.01; Gaussian Inc.: Wallingford, CT, USA, 2009.
12. [12]
13. [13]
14. [14]
1. [1]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
2. [2]
  Xu Liu , Chengxue Wu , Hui Li , Yang Wu . Computational chemistry-driven teaching reform of S_N2 reactions: quantitative analysis of competitive reaction pathways and pedagogical practice. University Chemistry, 2026, 41(7): 441-448. doi: 10.12461/PKU.DXHX202504109
3. [3]
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4. [4]
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5. [5]
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6. [6]
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7. [7]
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8. [8]
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9. [9]
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10. [10]
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11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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