A theoretical (DFT, GIAO-NMR, NICS) study of the carbocations and oxidation dications from azulenes, homoazulene, benzazulenes, benzohomoazulenes, and the isomeric azulenoazulenes

Organic and Biomolecular Chemistry

Volumn 1, Issue 17, 2003, Pages 3078-3093

  Okazaki, Takao ^a,b   Laali, Kenneth K ^b  

^a KYOTO UNIVERSITY   (Japan)

^b KENT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON ENERGY LEVELS; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; POSITIVE IONS; PROBABILITY DENSITY FUNCTION;

ANTIAROMATICITY; AROMATICITY; AZULENES; BENZAZULENES; CARBOCATIONS; DELOCALIZATION; DICATIONS; ISOMERIC AZULENOAZULENES; NUCLEOPHILIC ATTACK; PROTONATION;

AROMATIC COMPOUNDS;

AZULENE; AZULENE DERIVATIVE; CATION; CYCLOHEPTANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; PHYSICAL CHEMISTRY;

AZULENES; CATIONS; CHEMISTRY, PHYSICAL; CYCLOHEPTANES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 0141629737     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303865c     Document Type: Article

References (30)

1. P. de Wit and H. Cerfontain, Recl. Trav. Chim. Pays-Bas., 1985, 104, 25-36.
2. M. Oda, T. Kajioka, T. Okujima, S. Itoh, N. Morita, R. Miyatake and S. Kuroda, Chem. Lett., 1997, 1011-1012.
3. M. Oda, A. Sakamoto, T. Uchiyama, T. Kajioka, R. Miyatake and S. Kuoroda, Tetrahedron Lett., 1999, 40, 3595-3596.
4. M. Oda, T. Kajioka, Y. Kawamori, T. Uchiyama, S. Kuroda and N. Morita, Recent. Res. Dev. Org. Biorg. Chem., 2001, 4, 133-149.
5. M. Oda, H. Kainuma, R. Miyatake and S. Kuroda, Tetrahedron. Lett., 2002, 43, 3485-3488.
6. S. Ito, N. Morita and T. Asao, Bull. Chem. Soc. Jpn., 1991, 47, 6951-6966.
7. S. Ito, A. Nomura, N. Morita, C. Kabuto, H. Kobayashi, S. Maejima, K. Fujimuri and M. Yasunami, J. Org. Chem., 2002, 67, 7295-7302.
8. P. G. Lacroix, I. Malfant, G. Iftime, A. C. Razus, K. Nakatani and J. A. Delaire, Chem. Eur. J., 2000, 6, 2599-2608.
9. (a) L. T. Scott, W. R. Brunsvold, M. A. Kirms and I. Erden, J. Am. Chem. Soc., 1981, 103, 5216-5220
10. (b) L. T. Scott, C. A. Sumpter, M. Oda and I. Erden, Tetrahedron. Lett. 1989, 305-308.
11. (a) C. Jutz and E. Schweiger, Chem. Ber., 1974, 107, 2383-2396
12. (b) D. Sperandio and H.-J. Hansen, Helv. Chim. Acta, 1995, 78, 767-771
13. (c) R. A. Fallahpour and H.-J. Hansen, Helv. Chim. Acta, 1995, 78, 231.
14. D. Otteson, C. Jutz and J. Michl, J. Am. Chem. Soc., 1978, 100, 6882-6883.
15. E. Kloster-Jensen, E. Kovats, A. Eschenmoser and E. Heilbronner, Chem. Ind. (London), 1956, R38-9.
16. B. A. Hess Jr. and L. J. Schaad, J. Org. Chem., 1971, 36, 3418-3423.
17. (a) C. Jutz, H. G. Peuker and W. Kosbahn, Synthesis, 1976, 673
18. (b) T. Toda, N. Nishiwaki, T. Mukai and C. Kabuto, Tetrahedron. Lett, 1980, 21, 4001-4004
19. (c) S. Kuroda, S. Hirooka, H. Iwaki, M. Ikeda, T. Nakao, M. Ogitsu, M. Yasunami and T. Takase, Chem. Lett., 1986, 2039
20. (d) Z. Yoshida, M. Shibata, E. Ogino and T. Sugimoto, Tetrahedron. Lett, 1984, 25, 3343-3346
21. (e) T. Takayasu and M. Nitta, J. Chem. Soc., Perkin. Trans 2, 1997, 3537-3542.
22. (a) S. T. Howard, I. A. Fallis and D. J. Willock, Mol. Phys., 1999, 97, 913-918
23. (b) M. Buehl, W. Kozminski, A. Linden, D. Nanz, D. Sperandio and H.-J. Hansen, Helv. Chim. Acta, 1996, 79, 837-854
24. (c) S. Grimme, Chem. Phys. Lett., 1993, 201, 67-74.
25. Anomalies in computed NICS are not unprecedented (see: I. Alkotra, I. Rozas and J. Elguero, Tetrahedron, 2001, 57, 6043); origin of the unusually positive NICS value computed for 1,5,9-tridehydro[12]annulene was suggested to stem mainly from the choice of the DFT method employed.
26. N. S. Mills, J. Org. Chem., 1992, 57, 1899.
27. V. P. Reddy, D. R. Bellow and G. K. S. Prakash, J. Fluorine Chem., 1992, 56, 195-197.
28. 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. Morokuma, K. Cui, 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, 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 98 A9: Gaussian, Inc., Pittsburgh PA, 1998.
29. G. Schaftenaar and J. H. Noordik, J. Comput.-Aided Mol. Design, 2000, 14, 123.
30. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209.