Influence of alkene structure on the stability of alkene-Br2 complexes: Effect of chlorine substitution

Physical Chemistry Chemical Physics

Volumn 6, Issue 13, 2004, Pages 3235-3240

  Chiappe, Cinzia ^a   Lenoir, Dieter ^b   Pomelli, Christian Silvio ^c   Bianchini, Roberto ^d  

^a Dipartimento di Chimica Bioorganica   (Italy)

^b INSTITUTE OF EPIDEMIOLOGY   (Germany)

^c UNIVERSITY OF PISA   (Italy)

^d UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINE DERIVATIVE; CARBON; CHLORINE; ETHYLENE DERIVATIVE; TETRACHLOROETHYLENE; TRICHLOROETHYLENE;

AB INITIO CALCULATION; ARTICLE; CALCULATION; CORRELATION ANALYSIS; ELECTRON TRANSPORT; ENERGY; GEOMETRY; MEASUREMENT; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; ULTRAVIOLET RADIATION;

EID: 4043132378     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b316388a     Document Type: Article

References (30)

1. (a) T. Forster, Organic Charge-Transfer Complexes, Academic Press, London and New York, 1969;
2. (b) R. S. Mulliken and W. B. Person, Molecular Complexes, Wiley-Interscience, New York, 1969.
3. L. J. Andrews and R. M. Keefer, Molecular Complexes in Organic Chemistry, Holden-Day, San Francisco, 1964.
4. R. Rathore and J. K. Kochi, Adv. Phys. Org. Chem., 2000, 35, 193.
5. S. V. Rosokha and J. K. Kochi, J. Org. Chem., 2002, 67, 1727.
6. D. Lenoir and C. Chiappe, Chem. Eur. J., 2003, 9, 1036.
7. (a) van der Waals, Chem. Rev., 2000, 100 (11);
8. (b) A. Warshel, Theor. Chim. Acta, 2000, 103, 307.
9. (a) G. Bellucci, R. Bianchini and R. Ambrosetti, J. Am. Chem. Soc., 1985, 107, 2464;
10. (b) R. S. Brown, H. Slebocka-Tilk, G. Bellucci, R. Bianchini and R. Ambrosetti, J. Am. Chem. Soc., 1990, 112, 6310;
11. (c) G. Bellucci, R. Bianchini, C. Chiappe, V. R. Gadgil and A. P. Marchand, J. Org. Chem., 1993, 58, 3575;
12. (d) G. Bellucci, R. Bianchini, C. Chiappe, D. Lenoir and A. Attar, J. Am. Chem. Soc., 1995, 117, 6243;
13. (e) G. Bellucci, C. Chiappe, R. Bianchini, D. Lenoir and R. Herges, J. Am. Chem. Soc., 1995, 117, 12 001;
14. (f) R. Bianchini, C. Chiappe, D. Lenoir, P. Lemmen, R. Herges and J. Grunenberg, Angew. Chem., Int. Ed. Engl., 1997, 36, 1284;
15. (g) G. Bellucci, R. Bianchini, C. Chiappe, F. Marioni, R. Ambrosetti, R. S. Brown and H. Slebocka-Tilk, J. Am. Chem. Soc., 1989, 111, 2640;
16. (h) C. Chiappe, A. De Rubertis, P. Lemmen and D. Lenoir, J. Org. Chem., 2000, 65, 1273;
17. (i) C. Chiappe, A. De Rubertis, H. Detert, D. Lenoir, P. v. R. Schleyer and C. S. Wannere, Chem. Eur. J., 2002, 8, 967.
18. J.-E. Dubois and F. Garnier, Spectrochim. Acta, Part A, 1967, 23, 2288.
19. C. Chiappe, H. Detert, D. Lenoir, C. S. Pomelli and M. F. Ruasse, J. Am. Chem. Soc., 2003, 125, 2864.
20. C. Chiappe, A. De Rubertis, A. Jaber, D. Lenoir, C. Wattenbach and C. S. Pomelli, J. Org. Chem., 2002, 67, 7066.
21. W. B. Person, J. Am. Chem. Soc., 1965, 87, 167.
22. C. J. A. Byrnell, R. G. Coombes and M. C. Whiting, J. Chem. Soc., Perkin Trans. 2, 1983, 1079; G. Bellucci and C. Chiappe, J. Org. Chem., 1993, 58, 7120.
23. C. J. A. Byrnell, R. G. Coombes and M. C. Whiting, J. Chem. Soc., Perkin Trans. 2, 1983, 1079; G. Bellucci and C. Chiappe, J. Org. Chem., 1993, 58, 7120.
24. G. Bellucci, R. Bianchini, C. Chiappe, F. Marioni, R. Ambrosetti, R. S. Brown and H. Slebocka-Tilk, J. Am. Chem. Soc., 1989, 111, 2640.
25. max values of the complexes should decrease as the interaction decreases and the distance between donor and acceptor increases. However, several experimental works suggest that, in some cases, the opposite is the case. Several explanations of this behaviour have been given by different authors and they are reported in ref. 1a.
26. Recently very low formation constants of donor-acceptor complexes have been calculated also using the Benesi-Hildebrand correlation. See R. Rathore, S. V. Lindeman and J. K. Kochi, J. Am. Chem. Soc., 1997, 119, 9393.
27. CRC Handhook of Chemistry and Physics, ed. D. L. Lide, CRC press, NY, 78th edn., 1997.
28. E. D. Glendening, J. Am. Chem. Soc., 1996, 118, 2473; K. Morokuma, J. Chem. Phys., 1971, 55, 1236.
29. E. D. Glendening, J. Am. Chem. Soc., 1996, 118, 2473; K. Morokuma, J. Chem. Phys., 1971, 55, 1236.
30. Gaussian 99, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Gonzalez, P. M. W. Challacombe, B. G. Gill, W. Johnson, M. W. Chen, J. L. Wong, M. Andres, C. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.