The Distortive Tendency of Benzene π Electrons: How Is It Related to Structural Observables?

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 20, 1997, Pages 2205-2208

  Shurki, Avital ^a   Shaik, Sason ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Arenes; Bond length alternation; Cyclohexatriene; Strained molecules

Indexed keywords

EID: 0030662972     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199722051     Document Type: Article

References (29)

1. a) P. C. Hiberty, D. Danovich, A. Shurki, S. Shaik, J. Am. Chem. Soc. 1995, 117, 7760;
2. b) S. Shaik, A. Shurki, D. Danovich, P. C. Hiberty, ibid. 1996, 118, 666; see also
3. c) K. Jug, A. Köster, ibid. 1990, 112, 6772; d) A. Gobbi, Y. Yamaguchi, G. Frenking, H. F. Schaefer III, Chem. Phys. Lett. 1995, 244, 27.
4. c) K. Jug, A. Köster, ibid. 1990, 112, 6772; d) A. Gobbi, Y. Yamaguchi, G. Frenking, H. F. Schaefer III, Chem. Phys. Lett. 1995, 244, 27.
5. Y. Haas, S. Zilberg, J. Am. Chem. Soc. 1995, 117, 5387.
6. a) K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 9583;
7. b) H. B. Bürgi, K. K. Baldridge, K. Hardcastle, N. L. Frank, P. Gantzel, J. S. Siegel, J. Ziller, Angew. Chem. 1995, 107, 1575; Angew. Chem. Int. Ed. Engl. 1995, 34, 1454;
8. b) H. B. Bürgi, K. K. Baldridge, K. Hardcastle, N. L. Frank, P. Gantzel, J. S. Siegel, J. Ziller, Angew. Chem. 1995, 107, 1575; Angew. Chem. Int. Ed. Engl. 1995, 34, 1454;
9. c) N. L. Frank, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1995, 117, 2102.
10. a) R. Diercks, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 3150;
11. b) R. Boese, A. J. Matzger, D. L. Mohler, K. P. C. Vollhardt, Angew. Chem. 1995, 107, 1630; Angew. Chem. Int. Ed. Engl. 1995, 34, 1478;
12. b) R. Boese, A. J. Matzger, D. L. Mohler, K. P. C. Vollhardt, Angew. Chem. 1995, 107, 1630; Angew. Chem. Int. Ed. Engl. 1995, 34, 1478;
13. c) F. Cardullo, D. Giuffrida, F. H. Kohnke, F. M. Raymo, J. F. Stoddart, D. J. Williams, ibid. 1996, 108, 347 bzw. 1996, 35, 339.
14. c) F. Cardullo, D. Giuffrida, F. H. Kohnke, F. M. Raymo, J. F. Stoddart, D. J. Williams, ibid. 1996, 108, 347 bzw. 1996, 35, 339.
15. E. C. da Silva, J. Gerratt, D. L. Cooper, M. Raimondi, J. Chem. Phys. 1994, 101, 3866.
16. 2u-like) of 2 is always the first excited state but for 1 it is the second excited state according to all levels of calculation except STO-3G, in which it is predicted to be the first excited state.
17. Gaussian 94, Revision D.4: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
18. A molecule that is closely related to 2 was recently discussed by T. M. Krigowski, R. Anulewicz, P. C. Hiberty, J. Org. Chem. 1996, 61, 8533.
19. a) M. Merchán, E. Ortí, B. O. Roos, Chem. Phys. Lett. 1994, 221, 136;
20. b) J. Almlöf, T. H. Ficher, P. G. Gassman, A. Ghosh, M. Häser, J. Phys. Chem. 1993, 97, 10964.
21. a) S. Zilberg, Y. Haas, J. Chem. Phys. 1995, 103, 20;
22. b) S. Zilberg, S. Kendler, Y. Haas, J. Phys. Chem. 1996, 100, 10869.
23. A. Stanger, J. Am. Chem. Soc. 1991, 113, 8277.
24. E. D. Jemmis, B. Kiran, J. Org. Chem. 1996, 61, 9006.
25. For such a distorted σ framework see L. D. Mohler, K. P. Vollhardt, S. Wolff, Angew. Chem. 1990, 102, 1200; Angew;. Chem. Int. Ed. Engl. 1990, 29, 1151.
26. For such a distorted σ framework see L. D. Mohler, K. P. Vollhardt, S. Wolff, Angew. Chem. 1990, 102, 1200; Angew;. Chem. Int. Ed. Engl. 1990, 29, 1151.
27. 2 + const, and its minimum by Equation (1).
28. a) A. G. Ozkabak, L. Goodman, J. M. Berman, Chem. Phys. Lett. 1990, 168, 253;
29. b) for a summary, see S. Shaik, S. Zilberg, Y. Haas, Acc. Chem. Res. 1996, 29, 211.