Determination of the polarities of some ionic liquids using 2-nitrocyclohexanone as the probe

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 8193-8196

  Angelini, Guido ^a   Chiappe, Cinzia ^b   De Maria, Paolo ^a   Fontana, Antonella ^a   Gasparrini, Francesco ^c   Pieraccini, Daniela ^b   Pierini, Marco ^c   Siani, Gabriella ^a  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF PISA   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROCYCLOHEXANONE; CYCLOHEXANONE DERIVATIVE; IONIC LIQUID; ORGANIC SOLVENT; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; EQUILIBRIUM CONSTANT; INFRARED SPECTROSCOPY; ISOMER; LIQUID; MEASUREMENT; MOLECULAR PROBE; MOLECULAR STABILITY; PARAMETER; PRESSURE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUTE; SOLVENT EFFECT; ULTRAVIOLET SPECTROSCOPY;

EID: 25444445326     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050288g     Document Type: Article

References (48)

1. (a) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
2. (b) Rosini, G.; Ballini, R. Synthesis 1988, 833.
3. (c) Ballini, R. Synlett 1999, 1009.
4. Fischer, R. H.; Weitz, H. M. Synthesis 1980, 261.
5. Fontana, A.; De Maria, P.; Siani, G.; Pierini, M.; Cerritelli, S.; Ballini, R. Eur. J. Org. Chem. 2000, 1641.
6. Bell, R. P.; Robinson, R. R. Proc. R. Soc. A 1962, 270, 411.
7. Toullec, J. In The Chemistry of Enols; Rappoport, Z., Ed.; Wiley Sons: New York, 1990; p 323.
8. Laurence, C.; Nicolet, P.; Dalati, M. T.; Abboud, J.-L. M.; Notario, R. J. Phys. Chem. 1994, 98, 5807.
9. Reichardt, C. Chem. Rev. 1994, 94, 2319.
10. Buncel, E.; Rajagopal, S. J. Org. Chem. 1989, 54, 798.
11. Katritzky, A. R.; Fara, D. C.; Yang, H.; Tamm, K.; Tamm, T.; Karelson, M. Chem. Rev. 2004, 104, 175.
12. Wang, P.; Anderko, A. Fluid Phase Equilib. 2001, 186, 103.
13. Snyder, L. R. In Techniques of Chemistry; Perry, E. S., Weissberger, A., Eds.; Plenum Press: New York, 1978; pp 25-75.
14. (a) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223.
15. (b) Earle, M. J.; Seddon, M. K. R. Pure Appl. Chem. 2000, 72, 1391.
16. (c) Welton, T. Chem. Rev. 1999, 99, 2071.
17. (d) Wasserscheid, P.; Keim M. Angew. Chem., Int. Ed. 2000, 39, 3772.
18. (e) Sheldon, R. Chem. Commun. 2001, 2399.
19. (f) Olivier-Bourbigou, H.; Magna L. J. Mol. Catal. A 2002, 182, 419.
20. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
21. (h) Wilkes J. S. J. Mol. Chem. A 2004, 214, 11.
22. Ionic Liquids in Synthesis Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003.
23. (j) Welton T. Coord. Chem Rew. 2004, 248, 2459.
24. (a) Bonhôte, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Inorg. Chem. 1996, 35, 1168.
25. (b) Carda-Broch, S.; Berthod, A.; Armstrong, D. W. Anal. Bioanal. Chem. 2003, 375, 191.
26. (c) Giraud, G.; M. J.; Gordon, C. M.; Dunkin, I. R.; Wynne, K. J. Chem. Phys. 2003, 119, 464.
27. (a) Carmichael, A. J.; Seddon, K. R. J. Phys. Org. Chem. 2000, 13, 591.
28. (b) Dzyuba, S. V.; Bartsch, R. A. Tetrahedron Lett. 2002, 43, 4657.
29. (c) Muldoon, M. J.; Gordon, C. M.; Dunkin, I. R. J. Chem. Soc., Perkin Trans. 2 2001, 433.
30. (d) Aki, N. V. K.; Brennecke, J. F.; Samanta, A. Chem. Commun. 2001, 413.
31. (e) Fletcher, K. A.; Storey, I. A.; Hendricks, A. E.; Pandey, S.; Pandey, S. Green Chem. 2001, 3, 210.
32. (f) Poole, C. F. J. Chromatogr., A 2004, 1037, 49.
33. (a) Anderson, J. L.; Ding, J.; Welton, T.; Armstrong, D. W. J. Am. Chem. Soc. 2002, 124, 14247.
34. (b) Abraham, M. H.; Zissimos, A. M.; Huddleston, J. G.; Willauer, H. D.; Rogers, R. D.; Acree, W. E. Ind. Eng. Chem. Res. 2003, 42, 413.
35. (c) Ropel, L.; Belvèze, L. S.; Aki, S. N. V. K.; Stadtherr, M. A.; Brennecke, J. F. Green Chem. 2005, 7, 83.
36. Swiderski, K.; McLean, A.; Gordon, C. M.; Vaughan, D. H. Chem. Commun. 2004, 2178.
37. Crowhurst, L.; Mawdsley, P. R.; Perez-Arlndis, J. M.; Salter, P. A.; T. Welton, T. Phys. Chem. Chem. Phys. 2003, 5, 2790.
38. Earle, M. J.; Engel, B. S.; Seddon, K. R. Aust. J. Chem. 2004, 57, 149.
39. a of 23.0 has been reported for 1,3-dimethylimidazolium cation in water. Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366.
40. Morrow, T. I.; Maginn, E. J. J. Phys. Chem. B 2002, 106, 12807.
41. Gu, Z.; Brennecke, J. F. J. Chem. Eng. Data 2002, 47, 339.
42. (a) Baker, S. N.; Baker, G. A.; Kane, M. A.; Bright, F. V. J. Phys. Chem. B 2001, 105, 9663.
43. (b) Fletcher, K. A.; Baker, S. N.; Baker, G. A.; Pandey, S. New J. Chem. 2003, 1706.
44. Wang, P.; Anderko, A. Fluid Phase Equllib. 2001, 186, 103.
45. Cavell, E. A. S.; Knight, P. C. Z. Phys. Chem. Neue Folge 1968, 57, 331.
46. (a) Lancaster, N. L.; Salter, P. A.; Welton, T.; Young, G. B. J. Org. Chem. 2002, 67, 8855.
47. (b) Huddleston, J. G.; Willauer, H. D.; Swatlowski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765.
48. Billard, I.; Moutiers, G.; El Azzi, A.; Gaillard, C.; Mariet, C.; Lützenkinchen, K. Inorg. Chem. 2003, 42, 1726.