Photoelectron spectra, ab initio SCF MO, and natural bond orbital studies on stellenes. Long-range π/σ interactions

Journal of the American Chemical Society

Volumn 118, Issue 20, 1996, Pages 4889-4895

  Gleiter, Rolf ^a   Lange, Holger ^a   Borzyk, Oliver ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; PHOTOCHEMISTRY; THERMODYNAMICS;

EID: 0029973440     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954237k     Document Type: Article

References (39)

1. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
2. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
3. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
4. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
5. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
6. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
7. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
8. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499 . Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, Germany, 1988; p 115. Martin, H. D.; Mayer, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 283. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369. Eckert-Maksic, M. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer Verlag: Heidelberg, Germany, 1991; Part 3, p 153 and references therein.
9. Closs, G. L.; Miller, J. R. Science 1988, 240, 440. Miller, J. R. Nouv. J. Chem. 1987, 11, 83. Wasielewski, M. R. Chem. Rev. 1992, 92, 435. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395 and references therein.
10. Closs, G. L.; Miller, J. R. Science 1988, 240, 440. Miller, J. R. Nouv. J. Chem. 1987, 11, 83. Wasielewski, M. R. Chem. Rev. 1992, 92, 435. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395 and references therein.
11. Closs, G. L.; Miller, J. R. Science 1988, 240, 440. Miller, J. R. Nouv. J. Chem. 1987, 11, 83. Wasielewski, M. R. Chem. Rev. 1992, 92, 435. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395 and references therein.
12. Closs, G. L.; Miller, J. R. Science 1988, 240, 440. Miller, J. R. Nouv. J. Chem. 1987, 11, 83. Wasielewski, M. R. Chem. Rev. 1992, 92, 435. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395 and references therein.
13. (a) Bieri, G.; Heilbronner, E.; Kloster-Jensen, E.; Schmelzer, A.; Wirz, J. Helv. Chim. Acta 1974, 57, 1265.
14. (b) Gleiter, R.; Karcher, M.; Hahn, R.; Irngartinger, H. Chem. Ber. 1988, 121, 735.
15. (c) Gleiter, R.; Schäfer, W.; Sakurai, H. J. Am. Chem. Soc. 1985, 107, 3046.
16. Gleiter, R.; Toyota, A.; Bischof, P.; Krennrich, G.; Dressel, J.; Pansegrau, P. D., Paquette, L. A. J. Am. Chem. Soc. 1988, 110, 5490.
17. Gleiter, R.; Pfeifer, K. H.; Szeimies, G.; Bunz, K. Angew. Chem., Int. Ed. Engl. 1990, 29, 413.
18. Heilbronner, E.; Bock, H. Das HMO-Modell und seine Anwendung, Verlag Chemie, Weinheim, Germany, 1968. Dewar, M. J. S.; Dougherty, R. C. The PMO Theory of Organic Chemistry; Plenum Press: New York, 1975.
19. Heilbronner, E.; Bock, H. Das HMO-Modell und seine Anwendung, Verlag Chemie, Weinheim, Germany, 1968. Dewar, M. J. S.; Dougherty, R. C. The PMO Theory of Organic Chemistry; Plenum Press: New York, 1975.
20. Hoffmann, R.; Davidson, R. B. J. Am. Chem. Soc. 1971, 93, 5699. Salem. L.; Wright, J. S. J. Am. Chem. Soc. 1969, 91, 5947.
21. Hoffmann, R.; Davidson, R. B. J. Am. Chem. Soc. 1971, 93, 5699. Salem. L.; Wright, J. S. J. Am. Chem. Soc. 1969, 91, 5947.
22. Gleiter, R.; Kissler. B.; Ganter, C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1252.
23. Gleiter, R.; Borzyk, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
24. Koopmans, T. Physica 1934, 1, 104.
25. We used the Gaussian 92 program: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M. A.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Stewart, J. J. P.; Bobrowicz, F. W.; Rohlfing, C. W.; Kahn, L. R.; DeFrees, D. J.; Baker, J.; Pople, J. A. Gaussian 92; Gaussian Inc.: Pittsburgh. PA, 1992.
26. Heilbronner, E.; Schmelzer, A. Helv. Chim. Acta 1975, 58, 936.
27. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Weinhold, F. Ibid. 1983, 78, 4066.
28. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Weinhold, F. Ibid. 1983, 78, 4066.
29. Imamura, A.; Ohsaku, M. Tetrahedron 1981, 37, 2191. Using NBOs to analyze the TS/TB interaction: Liang, C.; Newton, M. D. J. Phys. Chem. 1992, 96, 2855. Naleway, C. A.; Curtiss, L. A.; Miller, J. R. J. Phys. Chem. 1991, 95, 8434. Paddon-Row, M. N.; Wong, S. S.; Jordan, K. D. J. Am. Chem. Soc. 1990, 112, 1710.
30. Imamura, A.; Ohsaku, M. Tetrahedron 1981, 37, 2191. Using NBOs to analyze the TS/TB interaction: Liang, C.; Newton, M. D. J. Phys. Chem. 1992, 96, 2855. Naleway, C. A.; Curtiss, L. A.; Miller, J. R. J. Phys. Chem. 1991, 95, 8434. Paddon-Row, M. N.; Wong, S. S.; Jordan, K. D. J. Am. Chem. Soc. 1990, 112, 1710.
31. Imamura, A.; Ohsaku, M. Tetrahedron 1981, 37, 2191. Using NBOs to analyze the TS/TB interaction: Liang, C.; Newton, M. D. J. Phys. Chem. 1992, 96, 2855. Naleway, C. A.; Curtiss, L. A.; Miller, J. R. J. Phys. Chem. 1991, 95, 8434. Paddon-Row, M. N.; Wong, S. S.; Jordan, K. D. J. Am. Chem. Soc. 1990, 112, 1710.
32. Imamura, A.; Ohsaku, M. Tetrahedron 1981, 37, 2191. Using NBOs to analyze the TS/TB interaction: Liang, C.; Newton, M. D. J. Phys. Chem. 1992, 96, 2855. Naleway, C. A.; Curtiss, L. A.; Miller, J. R. J. Phys. Chem. 1991, 95, 8434. Paddon-Row, M. N.; Wong, S. S.; Jordan, K. D. J. Am. Chem. Soc. 1990, 112, 1710.
33. Irngartinger, H.; Borzyk, O.; Gleiter, R. To be published.
34. Siemund. V.; Irngartinger, H.; Sigwart, C.; Kissler, B.; Gleiter, R. Acta Crystallogr. 1993, C49, 57.
35. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley & Sons: New York, 1986.
36. Hoffmann, R.; Mollère, P. D.; Heilbronner, E. J. Am. Chem. Soc. 1973, 95, 4860.
37. Paddon-Row, M. N.; Wong, S. S.; Jordan, K. D. J. Chem. Soc., Perkin Trans. 2 1990, 425.
38. Kissler, B.; Gleiter, R. Tetrahedron Lett. 1985, 26, 185.
39. Nakazaki, M.; Naemura, K.; Harada, H.; Narutaki, H. J. Org. Chem. 1982, 47, 3470.