Citation: Zhanhui Yang, Xufan Shen. Dewar Benzene and the Resonance Structures of Benzene[J]. University Chemistry, ;2021, 36(6): 200801. doi: 10.3866/PKU.DXHX202008014 shu

Dewar Benzene and the Resonance Structures of Benzene

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: 7 August 2020

The domestic organic chemistry textbooks use different numbers of contributing structures when introducing the resonance structures of benzene. This paper suggests that some of the related textbooks remove Dewar benzene and other ionic structures from the resonance structures of benzene, and adopt the correct resonance representation which constitutes only two Kekulé structures.
- Organic chemistry,
- Benzene,
- Resonance structure,
- Kekulé structure,
- Dewar bezene
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
  Kikuchi, S. J. Chem. Ed. 1997, 74, 194.
33. [33]
34. [34]
  Pauling, L. J. Am. Chem. Soc. 1931, 53, 3225.
35. [35]
  Pauling, L.; Wheland, G. W. J. Chem. Phys. 1933, 1, 362.
36. [36]
  van Tamelen, E. E.; Pappas, S. P. J. Am. Chem. Soc. 1962, 84, 37891.
37. [37]
  van Tamelen, E. E.; Pappas, S. P. J. Am. Chem. Soc. 1963, 85, 3297.
38. [38]
  van Tamelen, E. E. Acc. Chem. Res. 1972, 5, 186.
39. [39]
  Criegee, R.; Gruner, H. Angew. Chem. Int. Ed. 1968, 7, 467.
40. [40]
  Vollhardt, P. K.; Schore, N. Organic Chemistry:Structure and Function, 8th ed.; W. H. Freeman and Company:New York, NY, USA, 2018; p. 701.
41. [41]
  Solomans, T. W. G. Organic Chemistry, 4th ed.; John Wiley & Sons, Inc.:New York, NY, USA, 1988; p. 492.
42. [42]
  McMurry, J. Organic Chemistry, 9th ed.; Cengage Learning:Boston, MA, USA, 2016; p. 458.
43. [43]
  Wade, L.G., Jr. Organic Chemistry, 8th ed.; Pearson Education, Inc.:Glenview, IL, USA, 2013; p. 714.
44. [44]
  Brown, W. H.; Iverson, B. L.; Anslyn, E. V.; Foote, C. S.; Novak, B. M. Organic Chemistry, 8th ed.; Cengage Learning:Boston, MA, USA, 2018; p. 942.
45. [45]
  Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2rd ed.; Oxford University Press Inc.:New York, NY, USA, 2012; p. 473.
46. [46]
  Carey, F. A.; Giuliano, R. M. Organic Chemistry, 10th ed.; McGraw-Hill Education:New York, NY, USA, 2017; p. 416.
47. [47]
  Klein, D. Organic Chemistry, 2rd ed.; John Wiley Sons, Inc.:Hoboken, GA, USA, 2015; p. 838.
48. [48]
  Chaloner, P. Organic Chemistry:A Mechanistic Approach; CRC Press Taylor & Francis Group:Boca Raton, FL, USA, 2015; p. 66.
49. [49]
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