Do bicyclic forms of m- and p-benzyne exist?

European Journal of Organic Chemistry

Volumn , Issue 11, 2001, Pages 2185-2189

  Hess Jr , B Andes ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

Antiaroamticity; Aromaticity; Density functional calculations; Intermediates; Reaction mechanisms

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY; GEOMETRY; REACTION ANALYSIS; TEMPERATURE;

EID: 0011879863     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200106)2001:11<2185::AID-EJOC2185>3.0.CO;2-B     Document Type: Article

References (35)

1. R. W. Hoffmann, Dehydrobenzene and Cycloakenes; Academic Press, New York, 1967.
2. R. H. Levin, in: Reactive Intermediates (Eds.: M. Jones, R. A. Moss), Wiley, New York, 1985, vol. 1, p.1-18.
3. T. L. Gilchrist, Carbenes, Nitrenes and Arynes, Appleton-Century-Croft, NewYork, 1969.
4. J. D. Roberts, D. A. Semenow, H. E. Simmons, Jr., L. A Carlsmith, J. Am. Chem. Soc. 1956, 78, 601.
5. W. N. Washburn, R. Zahler, J. Am. Chem. Soc. 1975, 97, 1615.
6. W. N. Washburn, R. Zahler, J. Am. Chem. Soc. 1976, 98, 7827.
7. W. Sander, Acc. Chem. Res. 1999, 32, 669.
8. J. G. Radziszewski, B. A. Hess, Jr., R. Zahradnik, J. Am. Chem. Soc. 1992, 114, 52.
9. B. A. Hess, Jr., L. J. Schaad, Mol. Phys. 2000, 98, 1041.
10. K. N. Houk, M. Nendel, O. Wiest, J. W. Storer, J. Am. Chem. Soc. 1997, 119, 10545.
11. O. Wiest, K. N. Houk, in: Topics in Current Chemistry (Ed.: R. F. Nalewajski), Springer, Berlin, 1996, vol. 183, p. 1.
12. B. A. Hess, Jr., L. Smentek, Eur. J. Org. Chem. 1999, 3363.
13. J. Gräfenstein, K. Kraka, D. Cremer, Chem. Phys. Lett. 1998, 288, 593.
14. C. J. Cremer, J. Am. Chem. Soc. 1998, 120, 6261
15. The necessity of using unrestricted DFT has recently been pointed out for such singlet open-shell systems, see: J. Gräfenstein, E. Kraka, D. Cremer, Chem. Phys. Lett. 1998, 288, 593,
16. and: J. Gräfenstein, A. M. Hjerpe, E. Kraka, D. Cremer, J. Phys. Chem. A 2000, 104, 1748.
17. R. Marquardt, W. Sander, E. Kraka, Angew. Chem. Int. Ed. Engl. 1996, 35, 746.
18. R. Marquardt, A. Balster, W. Sander, E. Kraka, D. Cremer, J. G. Radziszewski, Angew. Chem. Int. Ed. 1998, 37, 955.
19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
20. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
21. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
22. D. E. Woon, T. H. Duning, Jr., J. Chem. Phys. 1993, 98, 1358.
23. R. A. Kendall, T.H. Dunning, Jr., R. J. Harrson, J. Chem. Phys. 1992, 96, 6796.
24. B. A. Hess, Jr., L. J. Schaad, J. Am. Chem. Soc. 1971, 92, 305.
25. J. O. Noell, M. D. Newton, J. Am. Chem. Soc. 1979, 101, 51.
26. K. Ohta, T. Shima, Chem. Phys. Lett. 1994, 217, 7.
27. M. J. S. Dewar, S. Kirschner, J. Am. Chem. Soc. 1971, 93, 4292.
28. [13]) which was done with UB3LYP/6-311+G(3d1f,3pld).
29. The relative intensities of the observed spectrum were reported only as weak or strong. In the plot the strong bands were arbitrarily assigned a relative intensity of 1.0 and the weak bands 0.25.
30. L. J. Schaad, B. A. Hess, Jr., Tetrahedron Lett. 1971, 17.
31. E. Kraka, D. Cremer, G. Bucher, H. Wandel, W. Sander, Chem. Phys. Lett. 1997, 268, 313.
32. K. K. Thoen, H. I. Kenttäamaa, J. Am. Chem. Soc. 1999, 121, 800.
33. E. D. Nelson, A. Artau, J. M. Price, H. I. Kenttämaa, J. Am. Chem. Soc. 2000, 122, 8781.
34. W. Sander, G. Bucher, H. Wandel, E. Kraka, D. Cremer, W. S. Sheldrick, J. Am. Chem. Soc. 1997, 119, 10660.
35. S. L. Debbert, C. J. Cramer, Int. J. Mass Spectrom. 2000, 201, 1.