Unusually high aromaticity and diatropicity of bond-alternate benzene

Journal of Physical Chemistry A

Volumn 114, Issue 2, 2010, Pages 1093-1097

  Aihara, Jun Ichi ^a   Ishida, Toshimasa ^b  

^a SHIZUOKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULENES; AROMATIC STABILIZATION ENERGIES; AROMATICITIES; BOND LENGTH ALTERNATION; MAGNETIC CHARACTER; THEORETICAL FRAMEWORK;

AROMATIC COMPOUNDS; AROMATIZATION; BENZENE;

BOND LENGTH;

EID: 75249084301     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp909141t     Document Type: Article

References (51)

1. Shaik, S. S.; Hiberty, P. C.; Lefour, J. M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363.
2. Shaik, S. S.; Hiberty, P. C.; Ohanessian, G.; Lefour, J. M. J. Phys. Chem. 1988, 92, 5086.
3. Glukhovtsev, M. N.; Simkin, B. Ya.; Minkin, V. I. Zh. Org. Khim. 1989, 25, 673.
4. Heilbronner, E. J. Chem. Educ. 1989, 66, 471.
5. Aihara, J. Bull. Chem. Soc. Jpn. 1990, 63, 1956.
6. Jug, J.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
7. Glendening, E. D.; Faust, R.; Streitwieser, A.; Volhardt, K. P. C.; Weinhold, F. J. Am. Chem. Soc. 1993, 115, 10952.
8. Boese, R.; Bläser, D.; Billups, W. E.; Haley, M. M.; Maulitz, A. H.; Mohler, D. L.; Vollhardt, K. P. C. Anvew. Chem., Int. Ed. Engl. 1994, 33, 313.
9. Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Mühlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298.
10. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
11. Alkorta, I.; Elguero, J. New J. Chem. 1999, 23, 951.
12. Cyrański, M. K.; Krygowski, T. M. Tetrahedron 1999, 55, 6205.
13. Fowler, P. W.; Rassat, A. Phys. Chem. Chem. Phys. 2002, 4, 1105.
14. Soncini, A.; Havenith, R. W. A.; Fowler, P. W.; Jenneskens, L. W.; Steiner, E. J. Org. Chem. 2002, 67, 4753.
15. Havenith, R. W. A.; Jenneskens, L. W.; Fowler, P. W. Chem. Phys. Lett. 2003, 367, 468.
16. Feixas, F.; Matito, E.; Poater, J.; Solà, M. J. Phys. Chem. A 2007, 111, 4513.
17. Feixas, F.; Matito, E.; Poater, J.; Sola, M. J. Comput. Chem. A 2008, 29, 1543.
18. Stanger, A. J. Phys. Chem. A 2008, 112, 12849.
19. Stanger, A. Chem. Commun. 2009, 1939.
20. Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789.
21. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Chapter 2. In Aromaticity and Antiaromaticity: Electronic and Structural Aspects; Wiley-Interscience: New York, 1994.
22. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750.
23. Gutman, I.; Milun, M.; Trinajstić, N. J. Am. Chem. Soc. 1977, 99, 1692.
24. Aihara, J.; Horikawa, T. Bull. Chem. Soc. Jpn. 1983, 56, 1853.
25. Aihara, J. J. Am. Chem. Soc. 1985, 107, 298.
26. Aihara, J. Bull. Chem. Soc. Jpn. 2004, 77, 651.
27. Aihara, J. J. Am. Chem. Soc. 2006, 128, 2873.
28. Aihara, J. J. Am. Chem. Soc. 1979, 101, 5913.
29. Aihara, J.; Horikawa, T. Chem. Phys. Lett. 1983, 95, 561.
30. Choi, C. H.; Kertesz, M. J. Chem. Phys. 1998, 108, 6681.
31. Wannere, C. S.; Sattelmeyer, K. W.; Schaefer, H. F., III; Schleyer. P. v. R. Aneew. Chem., Int. Ed. 2004, 43, 4200.
32. Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Ore. Lett. 2006, 8, 863.
33. Aihara, J. Chem. Phys. Lett. 2002, 365, 34.
34. Aihara, J.; Oe, S. Bull. Chem. Soc. Jpn. 2003, 76, 1363.
35. Schleyer, P. v. R.; Manoharan, M.; Wang, Z. X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E. Ore. Lett. 2001, 3, 2465.
36. Corminboeuf, C.; Heine, T.; Seifert, G.; Schleyer, P. v. R.; Weber, J. Phys. Chem. Chem. Phys. 2004, 6, 273.
37. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785.
38. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
39. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722.
40. Aihara, J. Bull. Chem. Soc. Jpn. 1980, 53, 1163.
41. Krygowski, T. M.; Cyranski, M. K. Chem. Rev. 2001, 101, 1385.
42. van Zijl, P. C. M.; Jenneskens, L. W.; Bastiaan, E. W.; MacLean, C.; de Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1986, 108, 1415.
43. Rice, J. E.; Lee, T. J.; Remington, R. B.; Allen, W. D.; Clabo, D. A.; Schaefer, H. F. J. Am. Chem. Soc. 1987, 109, 2909.
44. Gready, J. E.; Hambley, T. W.; Kakiuchi, K.; Kobiro, K.; Sternhell, S.; Tansey, C. W.; Tobe, Y. J. Am. Chem. Soc. 1990, 112, 7537.
45. Dijkstra, F.; van Lenthe, J. H. Int. J. Quantum Chem. 1999, 74, 213.
46. Caramori, G. F.; Galembeck, S. E.; Laali, K. K. J. Org. Chem. 2005, 70, 3242.
47. Jiao, H.; Schleyer, P. v. R. J. Phys. Org. Chem. 1998, 11, 655.
48. Matito, E.; Poater, J.; Duran, M.; Solà, M. THEOCHEM 2005, 727, 165.
49. Havenith, R. W. A.; Fowler, P. W.; Jenneskens, L. W.; Steiner, E. J. Phys. Chem. A 2003, 107, 1867.
50. Bodwell, G. J.; Bridson, J. N.; Cyrański, M. K.; Kennedy, J. W.; Krygowski, T, M,; Mannion, M. R.; Miller, D. O. J. Org. Chem. 2003, 68, 2089.
51. Zhang, B.; Manning, G. P.; Dobrowolski, M. A.; Cyrański, M. K.; Bodwell, G. J. Org. Lett. 2008, 10, 273.