A theoretical approach to understanding the fragmentation reaction of halonitrobenzene radical anions

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 5, 1999, Pages 1003-1009

  Pierini, Adriana B ^a   Duca Jr , José S ^a   Vera, Domingo M A ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001653146     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809210i     Document Type: Article

References (44)

1. (a) E. M. Arnett and R. A. Flowers, II, Chem. Soc. Rev., 1993, 22, 9;
2. (b) X.-M. Zhang, J. Chem. Soc., Perkin Trans. 2, 1993, 2275;
3. (c) K. Daasbjerg, J. Chem. Soc., Perkin Trans. 2, 1994, 1275;
4. (d) T. Clark, J. Am. Chem. Soc., 1988, 110, 1672.
5. J. M. Savéant, Adv. Phys. Org. Chem., 1990, 26, 1.
6. For example see: (a) W. C. Danen, T. T. Kensler, J. G. Lawless, M. F. Marcus and M. D. Hawley, J. Phys. Chem., 1969, 73, 4389;
7. (b) D. Behar and P. Neta, J. Phys. Chem., 1981, 85, 690;
8. (c) P. Neta and D. Behar, J. Am. Chem. Soc., 1981, 103, 103;
9. (d) M. Meot-Ner, P. Neta, R. K. Norris and K. Wilson, J. Phys. Chem., 1986, 90, 168.
10. D. Bethell, R. G. Compton and R. G. Welling, J. Chem. Soc., Perkin Trans. 2, 1992, 147.
11. R. G. Compton, R. A. W. Dryfe and A. C. Fisher, J. Electroanal. Chem., 1993, 361, 275.
12. R. G. Compton, R. A. W. Dryfe and A. C. Fisher, J. Chem. Soc., Perkin Trans. 2, 1994, 1581.
13. R. G. Compton and R. A. W. Dryfe, J. Electroanal. Chem., 1994, 375, 247.
14. R. G. Compton, R. A. W. Dryfe, J. C. Eklund, S. D. Page, J. Hirst, L. B. Nei, G. W. J. Fleet, K. Y. Hsia, D. Bethell and L. Martingale, J. Chem. Soc., Perkin Trans. 2, 1995, 1673.
15. Orbital isomers are defined as species distinguishable by different occupation of a set of available MOs. The MOs may be distinguished by symmetry, or by their nodal properties. See: M. J. S. Dewar, S. Kirschner and H. W. Kollmar, J. Am. Chem. Soc., 1974, 96, 5242.
16. (a) D. D. Clarke and C. A. Coulson, J. Chem. Soc. A, 1969, 169;
17. (b) R. Dressler, M. Allan and E. Haselbach, Chimia, 1985, 39, 385.
18. M. C. R. Symons, Acta Chem. Scand. 1997, 51, 127; M. C. R. Symons, Pure Appl. Chem., 1981, 53, 223.
19. M. C. R. Symons, Acta Chem. Scand. 1997, 51, 127; M. C. R. Symons, Pure Appl. Chem., 1981, 53, 223.
20. (a) M. J. S. Dewar and K. Narayanaswami, J. Am. Chem. Soc., 1964, 86, 2422;
21. (b) M. J. S. Dewar, A. H. Pakiari and A. B. Pierini, J. Am. Chem. Soc., 1982, 104, 3242.
22. See: L. Salem, Electrons in Chemical Reactions: First Principles, Wiley, New York, 1982.
23. (a) H. Villar, E. A. Castro and R. A. Rossi, Can. J. Chem., 1982, 60, 2525;
24. (b) H. Villar, E. A. Castro and R. A. Rossi, Z. Naturforsch., Teil A, 1984, 39, 49;
25. (c) J. Casado, I. Gallardo and M. Moreno, J. Electroanal. Chem., 1987, 219, 197;
26. (d) A. B. Pierini, J. S. Duca, Jr. and M. T. Baumgartner, J. Mol. Struct. (THEOCHEM), 1994, 311, 343;
27. (e) C. Glidewell, Chem. Scr., 1985, 25, 142;
28. (f) C. P. Andrieux, J. M. Savéant and D. Zann, Nouv. J. Chim., 1984, 8, 107;
29. (g) R. Benassi, C. Bertarini and F. Taddei, Chem. Phys. Lett., 1996, 257, 633.
30. A. B. Pierini and J. S. Duca, Jr., J. Chem. Soc., Perkin Trans. 2, 1995, 1821.
31. C. Amatore, C. Combellas, J. Pinson, M. A. Oturan, S. Robveille, J.-M. Savéant and A. Thiébault, J. Am. Chem. Soc. 1985, 107, 4846.
32. D. A. Liotard, E. F. Healy, J. M. Ruiz and M. J. S. Dewar, AMPAC version 2.1. Quantum Chemistry Program Exchange, program 506, QCPE Bull., 1989, 9, 123.
33. J. W. McIver and A. Komornicki, Chem. Phys. Lett., 1971, 10, 303; J. W. McIver and A. Komornicki. J. Am. Chem. Soc., 1972, 94, 265.
34. J. W. McIver and A. Komornicki, Chem. Phys. Lett., 1971, 10, 303; J. W. McIver and A. Komornicki. J. Am. Chem. Soc., 1972, 94, 265.
35. G. Rauhut and T. Clark, J. Chem. Soc., Faraday Trans., 1994, 90, 1783.
36. E. A. Halevi and M. Wolfsberg, J. Chem. Soc., Perkin Trans. 2, 1993, 1493.
37. M. J. S. Dewar and E. G. Zoebisch, J. Mol. Struct. (THEOCHEM), 1988, 180, 1.
38. The σ surface of chlorobenzene RA has been proposed as repulsive at all C-Cl separation distances but infinity. See ref. 10a.
39. -1 for p-chloronitrobenzene. This is reasonable considering the values observed and calculated for nitrobenzene. See for example: J. P. Ritchie, Tetrahedron, 1988, 44, 7465.
40. σπ was not corrected to take into consideration the "effective intra-ET distance" (see ref. 15).
41. V. D. Parker, Acta Chem. Scand., Ser. B. 1981, 35, 655.
42. R. G. Compton, R. G. Wellington, P. J. Dobson and P. A. Leigh, J. Electroanal. Chem., 1994, 370, 129.
43. W. C. Danen, T. T. Kensler, J. G. Lawless, M. F. Marcus and M. D. Hawley, J. Phys. Chem., 1969, 73, 4389.
44. T. Teherani and A. J. Bard, Acta Chem. Scand., Ser. B, 1983, 37, 413.