几种常见芳香化合物的稳定构象

引用本文: 许家喜, 麻远. 几种常见芳香化合物的稳定构象[J]. 大学化学, 2025, 40(12): 183-186. doi: 10.12461/PKU.DXHX202508007 shu

Citation: Jiaxi Xu, Yuan Ma. Stable Conformation of Several Common Aromatic Compounds[J]. University Chemistry, 2025, 40(12): 183-186. doi: 10.12461/PKU.DXHX202508007 shu

几种常见芳香化合物的稳定构象

许家喜 ^{1,
,} ,
麻远 ^2,

1.
北京化工大学化学学院, 北京 100029;
2.
清华大学化学系, 北京 100084

通讯作者: 许家喜,E-mail:jxxu@mail.buct.edu.cn

基金项目:
有机化学和中级有机化学一流课程建设项目

摘要: 芳香化合物的稳定构象是有机化学教学中的基本内容，对于讨论和判断芳香化合物的酸碱性和亲电反应的活性非常重要。现行教材中并没有很好地解释芳香化合物稳定构象的差别及其形成原因。本文通过分析不同芳香化合物中n-π₆⁶共轭效应和n-σ^*超共轭效应作用的强弱差别，以及氢键的参与作用，阐述和解释了几种常见的芳香化合物，如苯酚、苯胺、苯甲醚和三氟甲基苯基醚稳定构象的变化规律及形成原因。通过对多种电子效应和分子间相互作用的综合分析可以更好地理解这几类芳香化合物的稳定构象及其形成原因。

关键词:

English

Stable Conformation of Several Common Aromatic Compounds

Jiaxi Xu ^{1,
,} ,
Yuan Ma ^2,

1.
College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China;
2.
Department of Chemistry, Tsinghua University, Beijing 100084, China

Corresponding author: Jiaxi Xu, jxxu@mail.buct.edu.cn

Received Date: 05 August 2025
Revised Date: 21 October 2025
Available Online: 22 October 2025

Abstract: The stable conformations of aromatic compounds constitute fundamental contents in teaching organic chemistry. They play a crucial role to discuss and to identify acidity/basicity and reactive activity in the aromatic electrophilic substitution of these compounds. Current textbooks inadequately explain the variation in stable conformations of different aromatic compounds and their underlying causes. This study systematically examines several representative aromatic compounds, including phenol, anisole, aniline, and trifluoromethylbenzene, by analyzing the relative strengths of their n-π₆⁶ conjugation and n-σ^* hyperconjugation, as well as the involvement of hydrogen-bonding interactions. Through comprehensive evaluation of these electronic effects and intermolecular interactions, we elucidate the formations preferences and rationale their formation origins in these aromatic systems.

Key words:

1. [1]
  邢其毅, 裴伟伟, 徐瑞秋, 裴坚. 基础有机化学. 第4版. 北京: 北京大学出版社, 2017: 810.
2. [2]
  王彦广, 吕萍, 傅春玲, 马成. 有机化学. 第4版. 北京: 化学工业出版社, 2020: 395.
3. [3]
  Federsel, D.; Herrmann, A.; Christen, D.; Sander, S.; Willner, H.; Oberhammer, H. J. Mol. Struct. 2001, 567-568, 127.Federsel, D.; Herrmann, A.; Christen, D.; Sander, S.; Willner, H.; Oberhammer, H. J. Mol. Struct. 2001, 567-568, 127.
4. [4]
  Zhou, M.; Ni, C. F.; Zeng, Y. W.; Hu, J. B. J. Am. Chem. Soc. 2018, 140 (22), 6801.Zhou, M.; Ni, C. F.; Zeng, Y. W.; Hu, J. B. J. Am. Chem. Soc. 2018, 140 (22), 6801.
5. [5]
  Zavodnik, V. E.; Bel'skii, V. K.; Zorkii, P. M. J. Struct. Chem. 1988, 28, 793.Zavodnik, V. E.; Bel'skii, V. K.; Zorkii, P. M. J. Struct. Chem. 1988, 28, 793.
6. [6]
  Fukuyo, M.; Hirotsu, K.; Higuchi, T. Acta Cryst. 1982, B38, 640.Fukuyo, M.; Hirotsu, K.; Higuchi, T. Acta Cryst. 1982, B38, 640.
7. [7]
  Molenda, R.; Polkaehn, J.; Cordero, M. A. A.; Villinger, A.; Ehlers, P.; Lochbrunner, S.; Langer, P. J. Org. Chem. 2023, 88 (13), 8802.Molenda, R.; Polkaehn, J.; Cordero, M. A. A.; Villinger, A.; Ehlers, P.; Lochbrunner, S.; Langer, P. J. Org. Chem. 2023, 88 (13), 8802.
8. [8]
  Sahoo, A.; Deb, S.; Das, S.; Baitalik, S. Dyes and Pigments 2023, 218, 111425.Sahoo, A.; Deb, S.; Das, S.; Baitalik, S. Dyes and Pigments 2023, 218, 111425.
9. [9]
  Özkaraca, K.; Akkurt, M.; Shikhaliyev, N. Q.; Askerova, U. F.; Suleymanova, G. T.; Mammadova, G. Z.; Mlowe, S. Acta Cryst. E: Struct. Rep. Online 2021, 76, 1122,Özkaraca, K.; Akkurt, M.; Shikhaliyev, N. Q.; Askerova, U. F.; Suleymanova, G. T.; Mammadova, G. Z.; Mlowe, S. Acta Cryst. E: Struct. Rep. Online 2021, 76, 1122,
10. [10]
  Schulz, A.; Thomas, M.; Villinger, A. Dalton Trans. 2019, 48 (1), 125.Schulz, A.; Thomas, M.; Villinger, A. Dalton Trans. 2019, 48 (1), 125.
11. [11]
  Yanai, H.; Terajima, Y.; Kleemiss, F.; Grabowsky, S.; Matsumoto, T. Chem. Eur. J. 2023, 29 (15), e202203538.Yanai, H.; Terajima, Y.; Kleemiss, F.; Grabowsky, S.; Matsumoto, T. Chem. Eur. J. 2023, 29 (15), e202203538.
12. [12]
  许家喜, 麻远. 大学化学, 2024, 39 (11), 374.
13. [13]
  Lewis, D. E. Advanced Organic Chemistry; Oxford University Press: Oxford, UK, 2016.Lewis, D. E. Advanced Organic Chemistry; Oxford University Press: Oxford, UK, 2016.
14. [14]
  许薇, 许家喜. 大学化学, 2016, 31 (8), 60.
15. [15]
  许家喜, 麻远. 化学教育(中英文), 2022, 43 (24), 115.
16. [16]
  许家喜, 麻远. 大学化学, 2023, 38 (2), 109.
17. [17]
  许家喜, 麻远. 化学教育(中英文), 2024, 45 (4), 121.
18. [18]
  许家喜, 麻远. 化学教育(中英文), 2024, 45 (16), 105.
19. [19]
  许家喜, 麻远. 大学化学, 2024, 43 (24), 115.
20. [20]
  许家喜, 杨占会, 麻远. 化学教育(中英文), 2025, 46 (2), 126.
21. [21]
  Wang, J. D.; Li, P. F.; Yang, Z. H.; Chen, N.; Xu, J. X. Tetrahedron 2016, 72 (3), 370.Wang, J. D.; Li, P. F.; Yang, Z. H.; Chen, N.; Xu, J. X. Tetrahedron 2016, 72 (3), 370.
22. [22]
  Yuan, X.; Ke, X.; Xu, J. X. Org. Lett. 2022, 24 (49), 9141.Yuan, X.; Ke, X.; Xu, J. X. Org. Lett. 2022, 24 (49), 9141.

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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

几种常见芳香化合物的稳定构象

通讯作者: 许家喜,E-mail:jxxu@mail.buct.edu.cn

English

Stable Conformation of Several Common Aromatic Compounds

Corresponding author: Jiaxi Xu, jxxu@mail.buct.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

几种常见芳香化合物的稳定构象

通讯作者: 许家喜,E-mail:jxxu@mail.buct.edu.cn

English

Stable Conformation of Several Common Aromatic Compounds

Corresponding author: Jiaxi Xu, jxxu@mail.buct.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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