Aromaticity and its chemical manifestations

Theoretical and Computational Chemistry

Volumn 6, Issue C, 1999, Pages 519-536

  Wiberg, Kenneth B ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011613935     PISSN: 13807323     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1380-7323(99)80021-1     Document Type: Article

References (71)

1. Aromatic is defined as a substance "characterized by a fragrant smell, and usually a by a warm, pungent taste" (Merriam-Webster New International Dictionary), Reviews. Garratt P.J. Aromaticity (1986), Wiley, NY
2. Minkin V.J., Glukhovstsev M.N., and Simkin B.Y. Aromaticity and Antiaromaticity: Electronic and Structural Aspects (1994), Wiley, NY
3. Pauling L. J. Chem. Phys. 1 (1933) 280
4. Pauling L., and Wheland G.W. J. Chem. Phys. 1 (1933) 362
5. Pauling L., and Sherman J. J. Chem. Phys. 1 (1933) 679
6. Hückel E. Z. Physik. 70 (1931) 204
7. Hückel E. Z. Elektrochem. angew. physik. Chem. 42 (1937) 827
8. Ingold C.K. Structure and Mechanism in Organic Chemistry (1953), Cornell Univ. Press, Ithaca, NY 238. 5 When two or more significant resonance structures may be written for a molecule, it will be stabilized with respect to the basic structure. As a result, the energy required to reach the transition state will be increased unless there are corresponding interactions in the transition state. The latter will be the case for electrophilic substitution on anisole.
9. -. Bordwell F.G., Drucker G.E., and Fried H.E. J. Org. Chem. 46 (1981) 632
10. Doering W.v.E., and Knox L.H. J. Am. Chem. Soc. 76 (1954) 3203
11. Katz T.J. J. Am. Chem. Soc. 82 (1960) 3784
12. This is an example of Jahn-Teller distortion. Jahn H.A., and Teller E. Proc. Roy Soc. A161 (1937) 220
13. Breslow R., and Mazur S. J. Am. Chem. Soc. 95 (1973) 584
14. Bastiansen O., Hedberg L., and Hedberg K. J. Chem. Phys. 27 (1957) 1311
15. Wheland G. The Theory of Resonance and its Applications to Organic Chemistry (1944), Wiley, NY 94
16. Kawajima S. J. Am. Chem. Soc. 106 (1984) 6496
17. Maynau D., and Malrieu J.-P. J. Am. Chem. Soc. 104 (1982) 3029
18. Mulder J.J.L., and Oosterhoff L. J. Chem. Commun. (1970) 305
19. Mulder J.J.L., and Oosterhoff L. J. Chem. Commun. (1970) 307
20. Heitler W., and London F. Z. Physik. 44 (1927) 455
21. Wang S.C. Phys. Rev. 31 (1928) 579
22. Coulson C.A. Trans. Faraday Soc. 33 (1937) 1479
23. Weinbaum S. J. Chem. Phys. 1 (1933) 593. 16 In this simple example, configuration interaction serves mainly to correct for the use of a minimal basis set, and allows correct dissociation. When more complete basis sets are used, configuration interaction serves to correct for electron correlation.
24. Schultz P.A., and Messmer R.P. J. Am. Chem. Soc. 115 (1993) 10943
25. Bobrowicz F.W., and Goddard III W.A. In: Schaefer III H.F. (Ed). Methods of Modern Electronic Structure Theory. Vol. 3. Modern Theoretical Chemistry (1977), Plenum Press, NY
26. Parr R.G., and Yang W. Density-Functional Theory of Atoms and Molecules (1989), Oxford Univ. Press, NY 51ff
27. Coonradt H.L., and Hartaugh H.D. J. Am. Chem. Soc. 70 (1948) 1158
28. Blicke F.F., and Burckhalter J.H. J. Am. Chem. Soc. 64 (1942) 477
29. Pauling L. The Nature of the Chemical Bond. 3rd Ed (1960), Cornell Univ. Press, Ithaca 193
30. Kistiakowsky G.B., Ruhoff J.R., Smith H.A., and Waughan W.E. J. Am. Chem. Soc. 57 (1935) 876
31. Kistiakowsky G.B., Ruhoff J.R., Smith H.A., and Waughan W.E. J. Am. Chem. Soc. 58 (1936) 237
32. Kistiakowsky G.B., Ruhoff J.R., Smith H.A., and Waughan W.E. J.Am. Chem. Soc. 57 (1935) 146
33. Simpson W.T. J. Am. Chem. Soc. 75 (1953) 597
34. Wiberg, K. B. J. Org. Chem. 1977 to be published.
35. It should be noted that there is not general agreement on how stabilization energies should be calculated. Cf. Chestnut D.B., and Davis K.M. J. Comput. Chem. 18 (1997) 584
36. Cioslowski J., Liu G., Martinov M., Piskorz P., and Moncrieff D. J. Am. Chem. Soc. 118 (1966) 5261
37. Breslow R. Acct. Chem. Res. 6 (1973) 393
38. Coulson C.A., and Longuet-Higgins H.C. Proc. Roy. Soc. London A192 (1947) 16
39. Berry R.S. J. Chem. Phys. 35 (1961) 2253
40. Shaik S.S., and Bar R. Nouv. J. Chim. 8 (1984) 411
41. Hiberty P.C., Shaik S.S., Lefour J.-M., and Ohanessian G. J. Org. Chem. 50 (1985) 4657
42. Shaik S.S., Hiberty P.C., Lefour J.-M., and Ohanessian G. J. Am. Chem. Soc. 109 (1987) 363
43. Shaik S.S., Hiberty P.C., Lefour J.-M., and Ohanessian G. J. Am. Chem. Soc. 109 (1987) 363
44. Shaik S.S., Hiberty P.C., Lefour J.-M., and Ohanessian G. J. Phys. Chem. 92 (1988) 5086
45. Hiberty P.C. In: Gutman I., and Cyrin S.J. (Eds). Topics in Current Chemistry Vol. 153 (1990), Springer, New York 27
46. Jug K., and Koster A.M. J. Am. Chem. Soc. 112 (1990) 6772
47. Glendening E.D., Faust R., Streitwieser A., Vollhardt K.P.C., and Weinhold F. J. Am. Chem. Soc. 115 (1993) 10952
48. Cf. Hiberty P.C., Ohanessian G., Shaik S.S., and Flament J.P. Pure Appl. Chem. 65 (1993) 35
49. Fulton R.L. J. Phys. Chem. 97 (1993) 9516. 33 The π-bond index is less than 0.5 because there are also small 1,3 and 1,4 contributions.
50. Fulton R.L., and Mixon S.T. J. Phys. Chem. 97 (1993) 7530. 33 The π-bond index is less than 0.5 because there are also small 1,3 and 1,4 contributions.
51. Cf. Minkin, et al., ref. 1. Julg A., Francois Th. Theor. Chim. Acta 7 (1967) 249
52. Pauling L. J. Chem. Phys. 4 (1936) 673
53. Dauben Jr. H.J., Wilson J.D., and Laity J.L. J. Am. Chem. Soc. 90 (1968) 811
54. 1991. Dauben Jr. H.J., Wilson J.D., and Laity J.L. J. Am. Chem. Soc. 91 (1969)
55. Dauben Jr. J.J. Diamagnetic Susceptibility Exhaltation as a Criterion of Aromaticity. In: Snyder (Ed). Non-Benzenoid Aromatics Vol 2 (1971), Academic Press, NY
56. Pople J.A. J. Chem. Phys. 24 (1956) 111
57. Benson R.C., and Flygare W.H. J. Am. Chem. Soc. 92 (1970) 7523
58. Hutter D.H., and Flygare W.H. Top. Curr. Chem. 63 (1976) 1976
59. Schleyer P.v.R., and Jiao H. Pure and Appl. Chem. 68 (1996) 209
60. Cf. Vogel E., and Roth H.D. Angew. Chem. Int. Ed. Engl. 3 (1964) 228
61. Gaoni Y., Malera A., Sondheimer F., and Wolovsky R. Proc. Chem. Soc. (1964) 397
62. Boekelheide V., and Philips J.B. J. Am. Chem. Soc. 89 (1967) 1695
63. Baumann H., and Oth J.F.M. Helv. Chim. Acta 65 (1982) 1885
64. Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H., and van Eikema Hommes N.J.R. J. Am. Chem. Soc. 118 (1996) 6317
65. unpublished results. Cf. Feniak, G. Dauben Jr. H.J., and Feniak G. Ph. D. Thesis (1955), University of Washington
66. Wiberg K.B. Physical Organic Chemistry (1965), Wiley, NY 9
67. Dähne S., and Hoffmann K. Prog. Phys. Org. Chem. 18 (1990) 1
68. Dewar M.J.S., and Schmeising H.N. Tetrahedron 5 (1959) 166
69. Wiberg K.B., Nakaji D., and Breneman C.M. J. Am. Chem. Soc. 111 (1989) 4178
70. In: Gronowitz G. (Ed). Thiophene and Its Derivatives (1985), Wiley/Interscience, NY
71. Pauling L. The Nature of the Chemical Bond. 3rd Ed (1960), Cornell Univ. Press, Ithaca 220