Polarizability effects and dispersion interactions in alkene-Br2 π-complexes

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2864-2865

  Chiappe, Cinzia ^a   Detert, Heiner ^b   Lenoir, Dieter ^c   Pomelli, Christian Silvio ^a   Ruasse, Marie Françoise ^d  

^a UNIVERSITY OF PISA   (Italy)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

^c Institut fur Okologische Chemie   (Germany)

^d UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; ELECTRON TRANSPORT; GEOMETRY; IONIZATION; MOLECULAR INTERACTION; POLARIZATION;

EID: 0037433597     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027630g     Document Type: Article

References (37)

1. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
2. (a) van der Waals Complexes.III. Chem. Rev. Special Thematic Issue 2000, 100.
3. (b) Warshel, A. Theor. Chem. Acc. 2000, 103, 307.
4. (a) Forster, T. Organic Charge-Transfer Complexes; Academic Press: London and New York, 1969.
5. (b) Andrews, L. J.; Keefer, R. M. Molecular Complexes in Organic Chemistry; Holden-day: San Francisco, 1964.
6. (c) Rathore, R.; Kochi, J. K. Adv. Phys. Org. Chem. 2000, 35, 193.
7. (d) Rosokha, S. V.; Kochi, J. K. J. Org. Chem. 2002, 67, 1727.
8. Mulliken distinguishes "outer complexes" with small charge transfer between donor and acceptor and "inner complexes" with extensive charge redistribution. Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley-Interscience: New York, 1969.
9. Dubois, J.-E.; Garnier, F. Spectrochim. Acta, Part A 1967, 23, 2288.
10. (a) Bellucci, G.; Bianchini, R.; Ambrosetti, R. J. Am. Chem. Soc. 1985, 107, 2464.
11. (b) Brown, R. S.; Slebocka-Tilk, H.; Bellucci, G.; Bianchini, R.; Ambrosetti, R. J. Am. Chem. Soc. 1990, 112, 6310.
12. (c) Bellucci, G.; Bianchini, R.; Chiappe, C.; Gadgil, V. R.; Marchand, A. P. J. Org. Chem. 1993, 58, 3575.
13. (d) Bellucci, G.; Bianchini, R.; Chiappe, C.; Lenoir, D.; Attar, A. J. Am. Chem. Soc. 1995, 117, 6243.
14. (e) Bellucci, G.; Chiappe, C.; Bianchini, R.; Lenoir, D.; Herges, R. J. Am. Chem. Soc. 1995, 117, 12001.
15. (f) Bianchini, R.; Chiappe, C.; Lenoir, D.; Lemmen, P.; Herges, R.; Grunenberg, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1284.
16. (g) Bellucci, G.; Bianchini, R.; Chiappe, C.; Marioni, F.; Ambrosetti, R.; Brown, R. S.; Slebocka-Tilk, H. J. Am. Chem. Soc. 1989, 111, 2640.
17. (h) Chiappe, C.; De Rubertis, A.; Lemmen, P.; Lenoir, D. J. Org. Chem. 2000, 65, 1273.
18. Prinsette, J.; Seger, G.; Kochanski, E. J. Am. Chem. Soc. 1978, 100, 6941.
19. (a) Legon, A. C.; Thumwood, J. M. A. Phys. Chem. Chem. Phys. 2001, 3, 1397.
20. (b) Chiappe, C.; De Rubertis, A.; Detert, H.; Lenoir, D.; Schleyer, P. v. R.; Wannere, C. S. Chem.-Eur. J. 2002, 8, 967.
21. Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686.
22. (a) Nelsen, S. F.; Klein, S. J.; Triber, D. A., II; Ismagilov, R. F.; Powell D. R. J. Org. Chem. 1997, 62, 6539.
23. (b) Nelsen, S. F.; Reinhardt, L. A. J. Phys. Org. Chem. 2001, 14, 847.
24. eff.
25. Masclet, P.; Grosjean, D.; Mouvier, G.; Dubois, J. E. J. Electron. Relat. Phenom. 1973, 2, 225.
26. Taft, R. W.; Topsom, R. D. Prog. Phys. Org. Chem. 1987, 16, 1.
27. Essefar, M.; Bouab, W.; Lamsabhi, A.; Abboud, J.-L. M.; Notario, R.; Yáñez, M. J. Am. Chem. Soc. 2000, 122, 2300.
28. (a) Sergeev, G. B.; Serguchev, Yu. A.; Smirnov, V. V. Russ, Chem. Rev. 1973, 697.
29. (b) Sergeev, G. B.; Smirnov, V. V.; Bakarinova, G. A. Vestn. Mosk. Univ. Khim. 1974, 15, 358.
30. (a) Cammi, C.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 4690.
31. (b) α can also be obtained experimentally by refraction index measurements. Butcher, P. N.; Cotter, D. The Elements of Nonlinear Optics; Cambridge University Press: Cambridge, 1990.
32. 2-double bond distance in the complex, is 2.81 and 2.41 Å for 8 and 4, respectively.
33. -].
34. Ruasse, M. F.; Argile, A.; Bienvenue-Goëtz, E.; Dubois J.-E. J. Org. Chem. 1979, 44, 2758. Ruasse, M. F.; Zhang, B. L. J. Org. Chem. 1984, 49, 3207.
35. Ruasse, M. F.; Argile, A.; Bienvenue-Goëtz, E.; Dubois J.-E. J. Org. Chem. 1979, 44, 2758. Ruasse, M. F.; Zhang, B. L. J. Org. Chem. 1984, 49, 3207.
36. α.
37. Schmid, G. H.; Gordon, J. W. Can. J. Chem. 1986, 64, 2.