Citation: Zhanhui Yang, Xufan Shen. 苯的凯库勒式与苯的共振结构[J]. University Chemistry, ;2021, 36(8): 200901. doi: 10.3866/PKU.DXHX202009012 shu

苯的凯库勒式与苯的共振结构

Zhanhui Yang ^, ,
Xufan Shen

Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China

Corresponding author: Zhanhui Yang, zhyang@mail.buct.edu.cn
Received Date: 3 September 2020

国内外许多有机化学教材认为苯的两个共振极限式是凯库勒式。本文通过梳理苯环结构的研究历史和凯库勒式的结构特征，认为该说法并不妥当，并建议将苯的两个共振极限式命名为“Pauling结构式”或“Pauling苯”。
- Organic chemistry,
- Benzene,
- Resonance structure,
- Kekulé’s structure,
- Pauling benzene
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
  Carey, F. A. Organic Chemistry, 7th ed.; McGraw-Hill Higher Education:New York, USA, 2008; p. 424.
9. [9]
  Harold Hart, H.; Hadad, C. M.; Craine, L. E.; Hart, D. J. Organic Chemistry:A Short Course, 13rd ed.; Cengage Learning:Belmont, USA, 2012; p. 117.
10. [10]
  Ouellette, R. J.; Rawn, J. D. Principles of Organic Chemistry; Elsevier:Amsterdam, Netherlands, 2015; pp. 134-135.
11. [11]
  Wade, L. G., Jr. Organic Chemistry, 8th ed.; Pearson Education, Inc.:Glenview, USA, 2013; p. 714.
12. [12]
  Brown, W. H.; Iverson, B. L.; Anslyn, E. V.; Foote, C. S.; Novak, B. M. Organic Chemistry, 8th ed.; Cengage Learning:Boston, USA, 2018; p. 942.
13. [13]
  Carey, F. A.; Giuliano, R. M. Organic Chemistry, 10th ed.; McGraw-Hill Education:New York, USA, 2017; p. 416.
14. [14]
  Klein, D. Organic Chemistry, 2nd ed.; John Wiley Sons, Inc.:Hoboken, USA, 2015; p. 838.
15. [15]
  Morrison, R. T.; Boyd, R. N. Organic Chemistry,6th ed.; Prentice-Hall, Inc.:Englewood Cliffs, New Jersey, USA, 1992; p. 503.
16. [16]
  Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry,5th ed.; Springer:New York, USA, 2005; p. 18.
17. [17]
  Solomon, T. W. G.; Fryhel, C. B. Organic Chemistry, 9th ed.; John Wiley & Sons, Inc.:Hoboken, New Jersey, USA, 2008; p. 603.
18. [18]
  Vollhardt, P. K.; Schore, N. Organic Chemistry:Structure and Function, 8th ed.; W. H. Freeman and Company:New York, USA, 2018; p. 642.
19. [19]
  Smith, J. G. Organic Chemistry,4th ed.; McGraw-Hill:New York, USA, 2013; p. 632.
20. [20]
21. [21]
22. [22]
  Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press Inc.:New York, USA, 2012; p. 144.
23. [23]
24. [24]
  Smith, M. B. March's Advanced Organic Chemistry,7th ed.; John Wiley & Sons, Inc.:Hoboken, New Jersey, USA, 2013; p. 44.
25. [25]
  McMurry, J. Organic Chemistry, 9th ed.; Cengage Learning:Boston, USA, 2016; p. 145.
26. [26]
27. [27]
28. [28]
  Faraday, M. Phil. Trans. R. Soc. 1825, 115, 440.
29. [29]
  Mitscherlich, E. Ann. Pharm. 1834, 9, 39.
30. [30]
  Loschmidt, J. Chemische Studien; Carl Gerold's Sohn:Vienna, Austria-Hungary, 1861; p. 30, 65.
31. [31]
  Benfey, O. T. Kekulé Centennial; American Chemical Society:Washington, D. C., USA, 1966; p. 164-166.
32. [32]
  Kekulé, F. Α. Bull. Soc. Chim. Paris 1865, 3, 98.
33. [33]
  Kekulé, F. Α. Bull. Acad. Roy. Belg.1865,19, 551.
34. [34]
  Kekulé, F. Α. Liebigs Ann. Chem. Pharm. 1866,137, 129.
35. [35]
  Kekulé, F. Α. Zeitschrift für Chem. 1867, 3, 216.
36. [36]
  Kekulé, F. Α. Liebigs Ann. Chem. Pharm. 1872, 162, 77, 309.
37. [37]
  Walker, O. J. Ann. Sci. 1939, 4, 34.
38. [38]
  Lonsdale, K.Proc. R. Soc. Lond.1929,A123, 494.
39. [39]
  Pauling, L.; Wheland, G. W. J. Chem. Phys.1933,1, 362.
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