Home

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]
  Chaojie Li , Peng Fei , Yanhui Sun . Analysis of Question 9 on electrophilic aromatic substitution from the 38th China Chemistry Olympiad (Preliminary). University Chemistry, 2026, 41(7): 468-474. doi: 10.12461/PKU.DXHX202506075
4. [4]
  Xuefei Zhao , Xuhong Hu , Zhenhua Jia . 理论与计算化学在傅-克烷基化反应教学中的应用. University Chemistry, 2025, 40(8): 360-367. doi: 10.12461/PKU.DXHX202410008
5. [5]
  Hongyi Zhang , Zhihong Shi , Zhijun Zhang . A New Strategy for “De-formulized” Calculation of Dynamic Buffer Capacity in Analytical Chemistry Education. University Chemistry, 2024, 39(3): 390-394. doi: 10.3866/PKU.DXHX202309030
6. [6]
  Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
7. [7]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
8. [8]
  Junyu Peng , Feng Wang , Hongmei Yuan , Xiaoli Sun . Exploration of the “Sheep-Flock Effect” Teaching Model Based on Dual Preview: Taking Instrumental Analysis Experiment Courses in Local Universities as an Example. University Chemistry, 2025, 40(9): 310-317. doi: 10.12461/PKU.DXHX202412098
9. [9]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
10. [10]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
11. [11]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
12. [12]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
13. [13]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
14. [14]
  Yang Wang , Shuangliang Liu , Jianbo Zhao . Exploring the mechanism of Diels-Alder reaction: a computational chemistry experiment for undergraduate students. University Chemistry, 2026, 41(7): 257-265. doi: 10.12461/PKU.DXHX202504061
15. [15]
  Xueli Mu , Lingli Han , Tao Liu . Quantum Chemical Calculation Study on the E2 Elimination Reaction of Halohydrocarbon: Designing a Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 68-75. doi: 10.12461/PKU.DXHX202404057
16. [16]
  Hua Hou , Baoshan Wang . Course Ideology and Politics Education in Theoretical and Computational Chemistry. University Chemistry, 2024, 39(2): 307-313. doi: 10.3866/PKU.DXHX202309045
17. [17]
  Chunguang Rong , Miaojun Xu , Xingde Xiang , Song Liu . 化学热力学熵变计算的教学探讨. University Chemistry, 2025, 40(8): 323-329. doi: 10.12461/PKU.DXHX202409146
18. [18]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
19. [19]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
20. [20]
  Zhening Lou , Quanxing Mao , Xiaogeng Feng , Lei Zhang , Xu Xu , Yuyang Zhang , Xueyan Liu , Hongling Kang , Dongyang Feng , Yongku Li . Practice of Implementing Blended Teaching in Shared Analytical Chemistry Course. University Chemistry, 2024, 39(2): 263-269. doi: 10.3866/PKU.DXHX202308089

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(25)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return