Effects of steric congestion on stilbene radical anions and dianions: DFT calculations in the interpretation of stilbene radical anion ESR spectra

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6739-6743

  Gano, James E ^a   Jacob, E Jean ^a   Sekher, P ^a   Subramaniam, Girija ^a,d   Eriksson, Leif A ^b   Lenoir, Dieter ^c  

^a UNIVERSITY OF TOLEDO   (United States)

^b STOCKHOLM UNIVERSITY   (Sweden)

^c INSTITUTE OF EPIDEMIOLOGY   (Germany)

^d PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001726213     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960065d     Document Type: Article

References (41)

1. Mallory, F. B.; Mallory, C. W. Photocyclization of Stilbenes and Related Molecules; Wiley: New York, 1984; Vol. 30, pp 1-456.
2. (a) Meier, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1399-1420.
3. (b) Waldeck, D. H. Chem. Rev. 1991, 91, 415-436.
4. Goerner, H.; Kuhn, H. J. In Adv. Photochem.; Neckers; D. C., Volman, D. H., Von Buenau, G. V., Ed.; Wiley: New York, 1995; Vol. 19, pp 1-118.
5. Lenoir, D.; Gano, J. E.; McTague, J. A. Tetrahedron Lett. 1986, 27, 5339-5342.
6. Gano, J. E.; Subramaniam, G.; Birnbaum, R. J. Org. Chem. 1990, 55, 4760-4763.
7. Gano, J. E.; Park, B.-S.; Pinkerton, A. A.; Lenoir, D. J. Org. Chem. 1990, 55, 2688-2693.
8. Gano, J. E.; Park, B.-S.; Subramaniam, G.; Lenoir, D.; Gleiter, R. J. Org. Chem. 1991, 56, 4806-4808.
9. Gano, J. E.; Park, B. S.; Pinkerton, A. A.; Lenoir, D. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, 47, 162-164.
10. Laali, K. K.; Gano, J. E.; Lenoir, D.; Gundlach, C. W. I. J. Chem. Soc., Perkin Trans. 2 1994, 2169-2173.
11. Gano, J. E.; Skrzypczak-Jankun, E.; Kirschbaum, K.; Lenoir, D.; Frank, R. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 1985-1988.
12. Lenoir, D.; Burghard, H. J. Chem. Res., Synop. 1980, 396-397; J. Chem. Res., Miniprint 1980, 4715-4725.
13. Lenoir, D.; Burghard, H. J. Chem. Res., Synop. 1980, 396-397; J. Chem. Res., Miniprint 1980, 4715-4725.
14. Gerson, F.; Lamprecht, A.; Scholz, M.; Troxler, H.; Lenoir, D Helv. Chem. Acta 1996, 79, 307-318.
15. CAChe Reference Manual; CAChe Scientific: Beaverton, OR, 1993.
16. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
17. (a) Stewart, J. J. P. QCPE no. 581.
18. (b) Gano, J. E.; Jacob, E. J.; Roesner, R. J. Comput. Chem. 1991, 12, 127-134.
19. Gerson, F.; Ohya-Nishiguchi, H.; Szwarc, M.; Levin, G. Chem. Phys. Lett. 1977, 52, 587-589.
20. Nelsen, S. F. J. Chem. Soc., Perkin Trans. 2 1988, 1005-1008.
21. Glaser, R.; Choy, G. S.-C. J. Phys. Chem. 1993, 97, 3188-3198.
22. Glaser, R.; Choy, G. S.-C. J. Phys. Chem. 1994, 98, 11379-11393.
23. Malkin, V. G.; Malkina, O. L.; Eriksson, L. A.; Salahub, D. R. In Theoretical and Computational Chemistry; Seminario, J. M., Politzer, P., Ed.; Elsevier: Amsterdam, 1995; Vol. 2.
24. Higuchi, J.; Ishizu, K.; Nemoto, F.; Tajima, K.; Suzuki, H.; Ogawa, K. J. Am. Chem. Soc. 1984, 106, 5403-5407.
25. Gano, J. E.; Subramaniam, G.; Skrypczak-Jankun, E.; Kirschbaum, K.; Kluwe, C.; Sekher, P. Manuscript in preparation.
26. Sharp, J. H.; Symons, M. C. R. Ions and Ion-Pairs in Organic Reactions; 1972; Vol. 1, Chapter 5.
27. Gerson, F. High-Resolution ESR; Wiley-Verlag Chemie: 1970; Chapter A.2.2.
28. St-Amant, A.; Salahub, D. R. Chem. Phys. Lett. 1990, 169, 387.
29. St-Amant, A. Ph.D. Thesis, Universite de Montreal, 1991.
30. Salahub, D. R.; Fournier, R.; Mlynarski, P.; Papai, I.; St-Amant, A.; Ushio, J. In Density Function Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer Verlag: New York, 1991.
31. Daul, C.; Gourset, A.; Salahub, D. R. In Numerical Grid Methods and Their Applications to Schrodinger's Equation; Cerjan, C., Ed.; Kluwer: Dordrecht, 1993.
32. Perdew, J. P.; Wang, Y. Phys. Rev. B 1986, 33, 8800.
33. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
34. Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
35. Eriksson, L. A.; Malkin, V. G.; Malkina, O. L.; Salahub, D. R. J. Chem. Phys. 1993, 99, 9756.
36. Eriksson, L. A.; Malkina, O. L.; Malkin, V. G.; Salahub, D. R. J. Chem. Phys. 1994, 100, 5066.
37. Kim, K. S.; Lee, J. Y.; Lee, S. J.; Ha, T. K.; Kim, D. H. J. Am. Chem. Soc. 1994, 116, 7399-7400.
38. Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR-Basic Principles and Progress; Springer Verlag: Heidelberg, 1990; Vol. 23.
39. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
40. Beckhaus, H. D.; McCullough, K. J.; Fritz, H.; Ruechardt, C.; Kitschke, B.; Lindner, H. J.; Dougherty, D. A.; Mislow, K. Chem. Ber. 1980, 113, 1867-83.
41. Pine, S. H.; Munemo, E. M.; Phillips, T. R.; Bartolini, G.; Cotton, W. D.; Andrews, G. C. J. Org. Chem. 1971, 36, 984-91.