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

  • 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”。
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    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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