High Brønsted βnuc values in SNAr displacement. An indicator of the SET pathway?

Organic and Biomolecular Chemistry

Volumn 1, Issue 10, 2003, Pages 1757-1763

  Terrier, François ^a   Mokhtari, Malika ^a,b   Goumont, Régis ^a   Hallé, Jean Claude ^a   Buncel, Erwin ^c  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

^b UNIVERSITY OF TLEMCEN   (Algeria)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; BINARY MIXTURES; CHARACTERIZATION; CHARGE TRANSFER; ELECTRON TRANSITIONS; NEGATIVE IONS; OXIDATION; PHASE EQUILIBRIA; POSITIVE IONS; REACTION KINETICS; SUBSTITUTION REACTIONS;

ADDUCT LIKE TRANSITION; ANILINES; BRONSTED TYPE PLOTS; CHLORO NITROBENZOFURAN; NITROBENZOFURAZANYL IMIDAZOLIUM IONS; NUCLEOPHILIC AROMATIC SUBSTITUTION; PROTONATION EQUILIBRIA; SINGLE ELECTRON TRANSFER;

NITROGEN COMPOUNDS;

EID: 0141940230     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b301031g     Document Type: Article

References (81)

1. (a) W. P. Jencks, Bull. Soc. Chim. Fr., 1988, 218
2. (b) W. P. Jencks, in Nucleophilicity, ed. J. M. Harris and S. P. Mc Manus, Advances in Chemistry Series 215, American Chemical Society, Washington, DC, 1987, p. 155.
3. (a) A. Williams, Chem. Soc, Rev., 1994, 93
4. (b) M. Page and A. Williams, in Organic and Bio-organic Mechanisms, Longman, Harlow, Chapter 3
5. (c) M. Eigen, Angew. Chem., Int. Ed. Engl., 1964, 3, 1
6. (d) A. J. Kresge, Chem. Soc. Rev., 1973, 2, 475.
7. (a) F. G. Bordwell and W. J. Boyle, J. Am. Chem. Soc., 1972, 94, 3907
8. (b) F. G. Bordwell and J. A. Hautala, J. Org. Chem., 1978, 43, 3116 and references therein.
9. W. P. Jencks, M. T. Haber, D. Herschlag and K. L. Nazaretian, J. Am. Chem. Soc., 1986, 108, 479.
10. C. F. Bernasconi, Adv. Phys. Org. Chem., 1992, 27, 119 and references therein.
11. (a) W. P. Jencks, S. R. Brant, J. R. Gandler, G. Friedrich and C. Nakamura, J. Am. Chem. Soc., 1982, 104, 7045
12. (b) D. J. Hupe and W. P. Jencks, J. Am. Chem. Soc., 1977, 99, 451.
13. D. J. Hupe and D. Wu, J. Am. Chem. Soc., 1977, 99, 7653.
14. C. F. Bernasconi, Acc. Chem. Res., 1987, 20, 301.
15. (a) F. Terrier, G. Moutiers, L. Xiao, E. Le Guével and F. Guir, J. Org. Chem., 1995, 60, 1748
16. (b) E. Buncel, C. Cannes, A.-P. Chatrousse and F. Terrier, J. Am. Chem. Soc., 2002, 124, 8766 and references therein.
17. F. Terrier, P. Mc Cormack, E. Kizilian, J.-C. Hallé, P. Demerseman, F. Guir and C. Lion, J. Chem. Soc., Perkin Trans. 2, 1991, 153.
18. (a) M. I. Page and W. P. Jencks, J. Am. Chem. Soc., 1972, 94, 3263
19. (b) M. I. Page and W. P. Jencks, J. Am. Chem. Soc., 1972, 94, 8818.
20. F. G. Bordwell, J. C. Branca and T. A. Cripe, Isr. J. Chem., 1985, 26, 357.
21. F. G. Bordwell and A. H. Clemens, J. Org. Chem., 1981, 46, 1037.
22. F. G. Bordwell and D. L. Hugues, J. Am. Chem. Soc., 1986, 108, 5991.
23. (a) A. Hunter, M. Renfrew, D. Rettura, J. A. Taylor, J. M. Whitmore and A. Williams, J. Am. Chem. Soc., 1995, 117, 5484
24. J. Shakes, C. Raymond, D. Rettura and A. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 1553.
25. G. D. Leahy, M. Liverio, J. Miller and A. J. Parker, Aust. J. Chem., 1956, 9, 382.
26. F. Terrier, in Nucleophilic Aromatic Displacement, ed. H. Feuer, VCH, New-York, 1991, Chapters 1 and 2.
27. (a) F. Terrier, E. Kizilian, J.-C. Hallé and E. Buncel, J. Am. Chem. Soc., 1992, 114, 1740
28. (b) F. Terrier, Chem. Rev., 1982, 82, 77
29. (c) E. Buncel, R. A. Renfrow and M. J. Strauss, J. Org. Chem., 1987, 52, 488
30. (d) E. Buncel, R. A. Renfrow and M. J. Strauss, Can. J. Chem., 1983, 61, 1690
31. (e) R. A. Renfrow, M. J. Strauss, S. Cohen and E. Buncel, Aust. J. Chem., 1983, 36, 1843
32. (f) E. Buncel, J. M. Dust, K. T. Park, R. A. Renfrow and M. J. Strauss, in Nucleophilicity, ed. J. M. Harris and S. P. Mc Manus, Advances in Chemistry Series 215, American Chemical Society, Washington, DC, 1987, p. 369.
33. F. Terrier, M.-J. Pouet, J.-C. Hallé, E. Kizilian and E. Buncel, J. Phys. Org. Chem., 1998, 11, 707 and references cited therein.
34. R. Guomont, M. Sebban, P. Sepulcri, J. Marrot and F. Terrier, Tetrahedron, 2002, 58, 3249.
35. J.-C. Hallé, M. Mokhtari, P. Soulié and M.-J. Pouet, Can. J. Chem., 1997, 75, 1240.
36. G. Illuminati and F. Stegel, Adv. Heterocycl. Chem., 1983, 34, 305.
37. J. F. Bunnett, Q. Rev. Chem. Soc., 1958, 12, 1.
38. J. Miller, in Aromatic Nucleophilic Substitution, Elsevier; Amsterdam, 1968.
39. G. Consiglio, V. Frenna and D. Spinelli, Topics in Heterocyclic Systems - Synthesis, Reactions and Properties. Base Catalysis in Aromatic Nucleophilic Substitutions: Current Views. Research Signpost, Trivandrum (India), 1996, Vol. 1, p. 169.
40. O. Exner, in Correlation Analysis in Chemistry: Recent Advances. ed. N. B. Chapman and J. Shorter, Plenum Press, New York, 1978, Chapter 10: "A Critical Compilation of Substituent Constants."
41. C. F. Bernasconi, MTP Int. Rev. Sci.: Org. Chem., Ser. 1, 1973, 3, 33.
42. J.-C. Hallé, C. Pichon and F. Terrier, J. Biol. Chem., 1984, 259, 4142.
43. M. R. Crampton, J. Delaney and L. C. Rabbitt, J. Chem. Soc., Perkin Trans. 2, 1999, 2473.
44. F. G. Bordwell, Acc. Chem. Res., 1988, 22, 456.
45. J. J. Ryan and A. A. Humffray, J. Chem. Soc. B, 1967, 1300.
46. J. Hirst and K. U. Rahman, J. Chem. Soc., Perkin Trans. 2, 1973, 2119.
47. J. Kavalek, M. Pastrnek, and V. Sterba, Collect. Czech. Chem. Commun., 1978, 43, 1401.
48. L. Di Nunno, S. Florio and P. E. Todesco, J. Chem. Soc., Perkin Trans. 2, 1975, 1469.
49. J. E. Dixon and T.C. Bruice, J. Am. Chem. Soc., 1972, 94, 2052.
50. (a) N. R. Cullum, A. H. M. Renfrew, D. Rettura, J. A. Taylor, M. J. Whitemore and A. Williams, J. Am. Chem. Soc., 1995, 117, 9200
51. (b) A. H. M. Renfrew, J. A. Taylor, M. J. Whitemore and A. Williams, J. Chem. Soc., Perkin Trans. 2, 1994, 2383.
52. L. Grossi and S. Strazzari, J. Chem. Soc., Perkin Trans. 2, 1999, 2141.
53. C. Paradisi and G. Scorrano, Acc. Chem. Res., 1999, 32, 958.
54. T. Abe and Y. Ikegami, Bull. Chem. Soc. Jpn, 1977, 99, 6677.
55. L. A. Blyumenfeld, L. V. Bryukhovetskayar, G. V. Fomin and S. M. Shein, Russ. J. Phys. Chem., 1970, 44, 518 and references therein.
56. (a) R. Bacaloglu, C. A. Bunton and G. Cerichelli, J. Am. Chem. Soc., 1987, 109, 621
57. (b) R. Bacaloglu, C. A. Bunton and F. Ortega, J. Am. Chem. Soc., 1988, 110, 3503
58. (c) R. Bacaloglu, C. A. Bunton and F. Ortega, J. Am. Chem. Soc., 1988, 110, 3512.
59. (a) R. Bacaloglu, C. A. Bunton and F. Ortega, J. Am. Chem. Soc., 1989, 111, 1041
60. (b) R. Bacaloglu, A. Blasko, C. A. Bunton, E. Dorwin, F. Ortega and C. Zucco, J. Am. Chem. Soc., 1991, 113, 238.
61. G. Moutiers, J. Pinson, F. Terrier and R. Goumont, Chem. Eur. J., 2001, 7, 1712.
62. (a) I. M. Sosonkin and G. L. Kalb, Zh. Org. Khim., 1974, 10, 1341
63. I. M. Sosonkin, G. N. Strogov, A. Ya. Kaminskii, G. E. Troshin and F. F. Lakomov, Zh. Org. Khim., 1980, 16, 1711.
64. I. Gallardo, G. Guirado and J. Marquet, Chem. Eur. J., 2001, 7, 1759.
65. (a) I. Gallardo, G. Guirado and J. Marquet, J. Org. Chem., 2002, 67, 2548
66. (b) I. Gallardo, G. Guirado and J. Marquet, Eur. J. Org. Chem., 2002, 251
67. (c) I. Gallardo, G. Guirado and J. Marquet, Eur. J. Org. Chem., 2002, 261
68. (d) I. Gallardo, G. Guirado and J. Marquet, J. Electroanal. Chem., 2000, 488, 64.
69. L. Grossi, Tetrahedron Lett., 1992, 33, 5645.
70. V. Arca, C. Paradisi and G. Scorrano, J. Org. Chem., 1990, 55, 3617.
71. (a) A. S. Bailey and J. R. Case, Tetrahedron, 1958, 3, 113
72. (b) C. Boga and L. Forlani, J. Chem. Soc., Perkin Trans. 2, 2001, 1408
73. (c) L. Forlani, J. Phys. Org. Chem., 1999, 12, 417.
74. (a) M. Jonsson, J. Lind, T. E. Ericksen and G. Merényi, J. Am. Chem. Soc., 1994, 116, 1423
75. (b) J. Bacon and R. N. Adams, J. Am. Chem. Soc., 1968, 90, 6596.
76. (a) A. Pross, Acc. Chem. Res., 1985, 18, 212
77. (b) A. Pross and S. S. Shaik, Acc. Chem. Res., 1983, 16, 363
78. (c) L. Eberson and F. Radner, Acc. Chem. Res., 1987, 20, 53.
79. (a) H. A. Achassi Sorkhabi, J.-C. Hallé and F. Terrier, J. Chem. Res., 1978, 196 (S), 2545 (M)
80. (b) H. A. Achassi Sorkhabi, J.-C. Hallé and F. Terrier, J. Chem. Res., 1978, 1371 (M).
81. J.-C. Hallé, R. Gaboriaud and R. Schaal, Bull. Soc. Chim. Fr., 1969, 1851.