The energetics of valence isomerization in the norhornadiene-quadricyclane system

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4845-4847

  Bach, Robert D ^a   Schilke, Iliana L ^a   Schlegel, H Bernhard ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000984475     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952268s     Document Type: Article

References (26)

1. For a recent review, see: Bren', V. A.; Dubonsov, A. D.; Minkin, V. I.; Chernoivanov, V. A. Russ. Chem. Rev. 1991, 60, 451.
2. Miki, S.; Asako, Y.; Yoshida, Z. Chem. Lett. 1987, 195.
3. (a) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210.
4. (b) Roth, H. D.; Schilling, M. L. M.; Jones, G., II. J. Am. Chem. Soc. 1981, 103, 1246.
5. Ishiguro, K.; Khudyakov, I. V.; McGarry, P. F. Turro, N. J., Roth, H. D. J. Am. Chem. Soc. 1994, 116, 6933.
6. Raghavachari, K.; Haddon, R. C.; Roth, H. D. J. Am. Chem. Soc. 1983, 105, 3110.
7. (a) Kabakoff, D. S.; Bunzli, J. G.; Oth, J. M. F. Hammond, W. B.; Berson, J. B. J. Am. Chem. Soc. 1975, 97, 1810.
8. (b) Rogers, D. W.; Choi, L. S.; Girellini, R. S.; Holmes, T. J.; Allinger, N. L. J. Phys. Chem. 1980, 84, 1510.
9. (c) Steele, W. V. J. Chem. Thermodyn. 1978, 10, 919.
10. (a) Bach, R. D.; Mintcheva, I.; Estévez, C. M.; Schlegel, H. B. J. Am. Chem. Soc. 1995, 117, 10121.
11. (b) Stearns, R. A.; Paul R. Ortiz de Montellano J. Am. Chem. Soc. 1985, 107, 4081.
12. Schlegel, H. B. J. Phys. Chem. 1988, 92, 3075.
13. 10c using MP2/6-31G* geometries. All energies cited in the text are at the PMP4/ 6-31G*//MP2/6-31G* taking into account the zero-point energy unless specified otherwise.
14. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowki, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andrés, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Gaussian, Inc., Pittsburgh, PA, 1995.
15. (b) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
16. (c) Purvis, G. D. Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910.
17. (d) ACES II (Advanced Concepts in Electronic Structure Program System): Bartlett, R. J., Purvis, G. D., III, Fitzgerald, G. B., Harrison, R. J., Rittby, M., Sosa, C., Lee, Y. S., Trucks, G. W., Cole, S. J., Salter, E. A., Pal, S., Watts, J., Laidg, W. D., Magers, D. H., Stanton, J. F., Bernholdt, D.
18. (a) Allan, M. J. Electr. Spectrosc. Rel. Phen. 1989, 48 219.
19. (b) Helms, A. M.; Caldwell, R. A. J. Am. Chem. Soc. 1995, 117, 358.
20. (a) Burnell, E. E.; Diehl, P. Can. J. Chem. 1972, 50, 3566.
21. (b) Yokozeki, A.; Kuchitsu, K. Bull. Chem. Soc. Jpn. 1971, 44, 2356.
22. Mizuno, K.; Fukuyama, T.; Kuchitsu, K. Chem. Lett. 1972, 249.
23. 5 calculations show RMS errors of 0.026 Å and 0.617°.
24. (a) Haselbach, E.; Bally, T.; Lanyiova, Z.; Baertschi, P. Helv. Chim. Acta 1979, 62, 583.
25. (b) Taylor, G. N. Chem. Phys. Lett. 1971, 10, 355.
26. Gebicki, J. L.; Gebicki, J.; Mayer, J. Radiat. Phys. Chem. 1987, 30, 165.