Pseudo-Jahn - Teller distortion from planarity in heterocyclic seven- and eight-membered ring systems with eight π electrons

Journal of Physical Chemistry A

Volumn 107, Issue 15, 2003, Pages 2749-2756

  Toyota, Azumao ^a   Koseki, Shiro ^b   Umeda, Hiroaki ^b   Suzuki, Mika ^c   Fujimoto, Kazuyoshi ^c  

^a YAMAGATA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; ELECTRON ENERGY LEVELS; ELECTRONIC STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE;

NUCLEAR DEFORMATIONS;

ORGANIC POLYMERS;

EID: 0037452011     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0221284     Document Type: Article

References (59)

1. Borden, W. T. Chem. Rev. 1989, 89, 1095.
2. Szeimies, G. In Reactive Intermediates; Abramovitoh, R., Ed.; Plenum Press: New York, 1983; Vol. 3, pp 299-366.
3. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385.
4. Bock, H.; Ruppert, K.; Nather, C.; Halvas, Z.; Hermann, H.-F.; Arad, C.; Gobel, I.; John, A.; Meuret, J.; Nick, S.; Rauschenbach, A.; Seitz, W.; Vaupel, T.; Solouki, B. Angew. Chem., Int. Ed. Engl. 1992, 31, 550.
5. Zywietz, T. K.; Jiao, H.; Schleyer, P. v. R.; de Meijere, A. J. Org. Chem. 1998, 63, 3417.
6. Haag, R.; Fleischer, R.; Stalke, D.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1492.
7. Podlogar, B. L.; Glauser, W. A.; Rodriguez, W. R.; Raber, D. J. J. Org. Chem. 1989, 53, 2127.
8. (a) Gogonea, V.; Schleyer, P. v. R.; Schleyer, P. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1945.
9. (b) Mauksch, M.; Gogonea, V.; Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1998, 37, 2395.
10. Schleyer, P. v. R.; Maerker, A.; Dransfeld, H,; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.
11. Heilbronner, E. Tetrahedron Lett. 1964, 1923.
12. (a) Karney, W. L.; Kastrup, C. J.; Oldfield, S. P.; Rzepa, H. S. J Chem. Soc., Perkin Trans. 2 2002, 388.
13. (b) Kastrup, C. J.; Oldfield, S. P.: Rzepa, H. S. Chem. Commun. 2002, 642.
14. Jahn, H. A.; Teller, E. Proc. R. Soc. London, Ser. A 1937, 161, 220.
15. Opik, U.; Pryce, M. H. L. Proc. R. Soc. London, Ser. A 1957, 238, 425.
16. Bader, R. F. W. Can. J. Chem. 1962, 40, 1164.
17. Salem, L. The Molecular Orbital Theory of Conjugated Systems; W. A. Benjamin: New York, 1966 and references therein.
18. Engleman, R. The John - Teller Effect in Molecules and Crystals; Wiley-Interscience: London, 1972.
19. Pearson, R. G. Symmetry Rules for Chemical Reactions; Wiley: New York, 1976.
20. Toyota, A.; Tanaka, T.; Nakajima, T. Int. J. Quantum Chem. 1976, 10, 917 and references therein.
21. For a review, see Bersuker, I. B. Chem. Rev. 2001, 101, 1067. In this article, the role and place of the JT and pseudo-JT effects in theoretical chemistry are given. See also a recent paper: Atanasov, M.; Reinen, D. J Am. Chem. Soc. 2002, 124, 6693.
22. For a review, see Bersuker, I. B. Chem. Rev. 2001, 101, 1067. In this article, the role and place of the JT and pseudo-JT effects in theoretical chemistry are given. See also a recent paper: Atanasov, M.; Reinen, D. J Am. Chem. Soc. 2002, 124, 6693.
23. Toyota, A.; Shiota, M.; Nagae, Y.; Koseki, S. J. Phys. Chem. A 2001, 105, 1334.
24. Boyd, R. J.; Darvesh, K.; Fricker, P. D. J. Chem. Phys. 1991, 94, 8083. In this article, Boyd et al. put forth an interesting question regarding dominant factors responsible for the pure JT stabilization.
25. Wang, J.; Boyd, R. J. J. Chem. Phys. 1992, 96, 1232.
26. Ruedenberg, K.; Schmidt, R.; Dombek, M. M.; Elbert, S. T. J. Chem. Phys. 1982, 71, 41, 51, 65.
27. Schmidt, M. W.; Gordon, M. S. Annu. Rev. Phys. Chem. 1998, 49, 233.
28. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
29. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
30. The d exponent was 0.8 for carbon atoms.
31. Paul, I. C.; Johnson, S. M.; Paquette, L. A.; Barrett, J. H.; Haluska, R. J. J. Am. Chem. Soc. 1968, 90, 5023.
32. Paquette, L. A. Nonbenzenoid Aromatics; Snyder, J. P., Ed.; Academic Press: New York, 1969; Vol. l, p 250.
33. Perst, H.; Massa, W.; Lumm, M.; Baum, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 875.
34. Rieker, A.; Berger, S.; Mootz, D.; Steffen, M.; Wunderlich, H. Chem. Ber. 1982, 115, 385.
35. Drake, J. A. G.; Jones, D. W. Acta Crystallogr., Sect. B 1982, 38, 200.
36. McManus, M. J.; Berchtold, G. A.; Boyd, D. R.; Kennedy, D. A.; Malone, J. F. J. Org. Chem. 1986, 51, 2784.
37. Schneiders, C.; Huber, W.; Lex, J.; Mullen, K. Angew. Chem., Int. Ed. Engl. 1985, 24, 576.
38. (a) Gompper, R.; Schwarzensteiner, M.-L. Angew. Chem., Int. Ed. Engl. 1983, 22, 543.
39. (b) Ehrenberg, S.; Gompper, R.; Polborn, K.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1991, 30, 334.
40. Umeda, H.; Koseki, S.; Nagashima, U.; Schmidt, M. W. J. Comput. Chem. 2001, 22, 1243 and references therein.
41. Ichikawa, H.; Ebisawa, Y. J. Am. Chem. Soc. 1985, 107 1161.
42. Lowdin, P.-O. J. Mol, Spectrosc. 1959, 3, 46.
43. Parr, R. G.; Brown, J. E. J. Chem. Phys. 1968, 49, 4849.
44. Nelander, B. J. Chem. Phys. 1969, 51, 469.
45. Srebrenik, S.; Messer, R. J. Chem. Phys. 1975, 63, 2768.
46. Schmidt, M. W.; Baldridge, K K.; Boats, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A., Jr. J. Comput. Chem. 1993, 14, 1345.
47. Borden, W. T. J. Am. Chem. Soc. 1975, 97, 5968.
48. Kollmar, H.; Staemmler, V. J. Am. Chem. Soc. 1977, 99, 3583. Kollmar, H.; Staemmler, V. Theor. Chim. Acta 1978, 48, 223.
49. Kollmar, H.; Staemmler, V. J. Am. Chem. Soc. 1977, 99, 3583. Kollmar, H.; Staemmler, V. Theor. Chim. Acta 1978, 48, 223.
50. Koseki, S.; Nakajima, T.; Toyota, A. Can. J. Chem. 1985, 63, 1572.
51. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833, 1841, 2338, 2343.
52. Sorensen, G. O.; Mahler, L.; Rastrup-Andersen, N. J. Mol. Struct. 1974, 20, 119.
53. (a) Anet, F. A. L. J. Am. Chem. Soc. 1964, 86, 458.
54. (b) Jensen, F. R.; Smith, L. A. J. Am. Chem. Soc. 1964, 86, 956. The experimental activation energy for the inversion process is 6.3 kcal/mol in the former and 5.7 kcal/mol in the latter.
55. Bak, B.; Christensen, D.; Dixon, W. D.; Hansen-Nygaard, L.; Rastrup-Anderson, J.; Schottlander, M. J. Mol. Spectrosc. 1962, 9, 124.
56. Lister, D. G.; Tyler, J. K.; Hong, J. H.; Larsen, N. W. J. Mol. Struct. 1974, 23, 253.
57. Feinberg, M. J.; Ruedenberg, K.; Mehler, E. L. Adv. Quantum Chem. 1970, 4, 27.
58. Feinberg, M. J.; Ruedenberg, K. J. Chem. Phys. 1971, 54, 1495.
59. Koseki, S.; Toyota, A. J. Phys. Chem. A 1997, 101, 5712.