Acidity inversions of α-NO2 and α-SO 2CF3 activated carbon acids as a result of contrasting solvent effects on transfer from water to dimethyl sulfoxide solutions

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6566-6570

  Goumont, Régis ^a   Magnier, Emmanuel ^a   Kizilian, Elyane ^a   Terrier, François ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

HYPERCONJUGATION;

ACIDITY; ACTIVATED CARBON; ELECTRONS; IONIZATION; POLARIZATION;

NITROGEN OXIDES;

ACETIC ACID ETHYL ESTER; CARBON NITROGEN MONOCYCLE; DIMETHYL SULFOXIDE; FLUORINE DERIVATIVE; NITROGEN DIOXIDE; SOLVENT; SULFUR DIOXIDE; WATER;

ACIDITY; ARTICLE; ELECTRON TRANSPORT; ION TRANSPORT; IONIZATION; PKA; POLARIZATION;

EID: 0041508376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034244o     Document Type: Article

References (56)

1. (a) Richard, J. P. In The Chemistry of Enols; Rappoport, Z., Ed.; Wiley: New York, 1990.
2. (b) Nielsen, A. T. In Nitrones, Nitronates and Nitroxides; Breuer, E., Aurich, H. G., Nielsen, A. T., Eds.; Wiley: New York, 1989.
3. (c) Buncel, E. In Carbanions: Mechanistic and Isotopic Aspects; Eaborn, C., Chapman, N. B., Eds.; Elsevier: Amsterdam, 1975; Chapter 2, pp 60-64.
4. (a) Bradamante, S.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1986, 1035.
5. (b) Abbotto, A.; Bradamante, S.; Pagani, G. A. J. Org. Chem., 1993, 58, 449.
6. (a) Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
7. (b) Bernasconi, C. F.; Wenzel, P. J. J. Am. Chem. Soc. 1996, 118, 11446.
8. Richard, J. P.; Williams, G.; Gao, J. J. Am. Chem. Soc. 1999, 121, 715.
9. (a) Simpkins, N. S. In Sulfones in Organic Synthesis; Pergamon Press: Oxford, U.K., 1993.
10. (b) Oae, S.; Uchida, Y. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: New York, 1988.
11. Bordwell, F. G.; Vanier, N. R.; Matthews, W. S.; Hendrickson, J. B.; Skipper, P. L. J. Am. Chem. Soc. 1975, 97, 7160.
12. Wolfe, S.; Bernardi, F.; Csizmadia, I. G.; Mangini, A. In Organic Sulfur Chemistry; Elsevier: Amsterdam, 1985; pp 133-190.
13. Koch, R.; Anders, E. J. Org. Chem. 1994, 59, 4529.
14. Schleyer, P. v. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Arad, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 6467.
15. Gais, H. J.; Müller, J.; Vollhardt, J.; Lindner, H. J. J. Am. Chem. Soc. 1991, 113, 4002.
16. Raabe, G.; Gais, H. J.; Fleischhauer, J. J. Am. Chem. Soc. 1996, 118, 4622.
17. Wiberg, K. B.; Castejon, H. J. Am. Chem. Soc. 1994, 116, 10489.
18. Bernasconi, C. F.; Kittredge, K. W. J. Org. Chem. 1998, 63, 1944.
19. Yagupol'skii, L. M.; Il'chenko, A. Y.; Kondratenko, N. B. Usp. Khim. 1974, 43, 64.
20. (a) Sheppard, W. J. Am. Chem. Soc. 1963, 85, 1314.
21. (b) Exner, O. In Correlation in Chemistry; Chapman, N. B., Shorter, J., Eds.: Plenum Press: New York, 1978; Chapter 10.
22. (a) Yagupol'skii, L. M.; Gogoman, I. V.; Shchupak, G. M.; Boiko, V. N. Zh. Org. Chem. 1986, 22, 743.
23. (b) Yagupol'skii, L. M. In Aromatic and Heterocyclic Compounds with Fluorine Containing Substituents; Naukova Dumka: Kiev, Ukraine, 1988.
24. (a) Terrier, F. Chem. Rev. 1982, 82, 77.
25. (b) Terrier, F.; Millot, F.; Morel, J. J. Org. Chem. 1976, 41, 3892.
26. (c) Mokhtari, M.; Goumont, R.; Halle, J.-C.; Terrier, F. Arkivoc 2002, XI, 168.
27. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
28. Terrier, F.; Kizilian, E.; Goumont, R.; Faucher, N.; Wakselman, C. J. Am. Chem. Soc. 1998, 120, 9496.
29. Koppel, A. I.; Taft, R. W.; Anvia, F.; Zhu, S.-Z.; Hu, L.-Q.; Sung, K.-S.; DesMarteau, D. D.; Yagupol'skii, L. M.; Yagupol'skii, Y. L.; Ignatev, N. V.; Kondratenko, N. V.; Volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maria, P.-C. J. Am. Chem. Soc. 1994, 116, 3047.
30. (a) Koppel, A. I.; Koppel, J.; Leito, I. V.; Koppel, I.; Mishima, M.; Yagupol'skii, L. M. J. Chem. Soc., Perkin Trans. 2 2001, 229.
31. (b) Yagupol'skii, L. M.; Petrick, V. N.; Kondratenko, N. V.; Soväli, L.; Kaljürand, I.; Leito, I. V.; Koppel, A. I. J. Chem. Soc., Perkin Trans. 2 2002, 1950.
32. Crampton, M. R.; Robotham, I. A. J. Chem. Res., Synop. 1997, 22.
33. Bordwell, F. G.; Algrim, D. J. J. Am. Chem. Soc. 1988, 110, 2964.
34. Moutiers, G.; Thuet, V.; Terrier, F. J. Chem. Soc., Perkin Trans. 2 1997, 1479.
35. Bernasconi, C. F.; V. Kliner, D. A.; Mullin, A. S.; Ni, J. X. J. Org. Chem. 1988, 53, 3342.
36. Kresge, A. J. Acc. Chem. Res. 1990, 23, 43.
37. Bernasconi, C. F.; Montañez, R. L. J. Org. Chem. 1997, 62, 8162.
38. m)(PhCO) = 0.45.
39. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
40. Bernasconi, C. F.; Bunnell, R. D. Isr. J. Chem. 1985, 26, 420.
41. Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327.
42. Buncel, E.; Wilson, H. Adv. Phys. Org. Chem. 1977, 14, 133.
43. Browne, S. E.; Asher, S. E.; Cornwall, E. H.; Frisoli, J. K.; Harris, L. J.; Salot, E. A.; Sauter, E. A.; Trecoske, M. A.; Veale, P. S., Jr. J. Am. Chem. Soc. 1984, 106, 1432.
44. Moutiers, G.; El Fahid, B.; Goumont, R.; Chatrousse A. P.; Terrier, F. J. Org. Chem. 1996, 61, 1978.
45. Bowden, K.; Stewart, R. Tetrahedron 1965, 21, 261.
46. (a) Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463.
47. (b) Yokoyama, T.; Hanazome, I.; Mishima, M.; Kamlet, M. J.; Taft, R. W. J. Org. Chem. 1987, 52, 163.
48. Adolph, H. G.; Kamlet, M. J. J. Am. Chem. Soc. 1966, 88, 4761.
49. Bordwell, F. G.; Branca, J. C.; Bares, J. E.; Filler, R. J. Org. Chem. 1988, 53, 780.
50. Eugene, F.; Langlois, B.; Laurent, E. J. Fluorine Chem. 1994, 66, 301.
51. (a) Hallé, J. C.; Gaboriaud, R.; Schaal, R. Bull. Soc. Chim. Fr. 1970, 2047.
52. (b) Sorkhabi, H. A.; Hallé, J. C.; Terrier, F. J. Chem. Res., Synop. 1978, 196.
53. (a) Terrier, F.; Moutiers, G.; Xiao, L.; Le Guével, E.; Guir, F. J. Org. Chem. 1995, 60, 1748.
54. (b) Terrier, F.; MacCornack, P.; Kizilian, E.; Hallé, J. C.; Demerseman, P.; Guir, F.; Lion, C. J. Chem. Soc., Perkin Trans. 2 1992, 153.
55. (a) Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006.
56. (b) Bordwell, F. G.; Branca, J. C.; Hughes, D. L.; Olmstead, W. N. J. Org. Chem. 1980, 45, 3305.