P-nitrophenolate: A probe for determining acid strength in ionic liquids

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 1952-1956

  D'Anna, Francesca ^a   La Marca, Sandra ^a   Noto, Renato ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACID STRENGTHS; ACIDITY SCALE; LIQUID SOLUTIONS; MUTUAL INTERACTIONS; PROTONATION EQUILIBRIUM; ROOM-TEMPERATURE IONIC LIQUIDS; WATER SOLUTIONS;

CARBOXYLIC ACIDS; IONIC STRENGTH; IONIZATION OF LIQUIDS; IONS; ORGANIC ACIDS; SODIUM;

IONIC LIQUIDS;

4 NITROPHENOLATE; CARBOXYLIC ACID DERIVATIVE; IONIC LIQUID; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ACIDITY; ARTICLE; CHEMICAL STRUCTURE; PROTON TRANSPORT; ROOM TEMPERATURE; SPECTROPHOTOMETRY;

CARBOXYLIC ACIDS; HYDROGEN-ION CONCENTRATION; IONIC LIQUIDS; MOLECULAR STRUCTURE; NITROPHENOLS; SOLUTIONS; WATER;

EID: 64249113439     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802473p     Document Type: Article

References (61)

1. (a) Bosch, E.; Rived, F.; Rosés, M.; Sales, J. J. Chem. Soc., Perkin Trans.2 1999, 1953-1958.
2. (b) Andonovski, B. S. Croat. Chem. Acta 1999, 72, 711-726.
3. (c) Abdur-Rashid, K.; Fong, T. P.; Greaves, B.; Gusev, D. G.; Hinman, J. G.; Landau, S. E.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2000, 122, 9155-9171.
4. (d) Rived, F.; Canals, I.; Bosch, E.; Rosés, M. Anal. Chim. Acta 2001, 439, 315-333.
5. (e) Espinosa, S.; Bosch, E.; Rosés, M. J. Cromatogr. A 2002, 964, 55-66.
6. (f) Magill, A. M.; Yates, B. F. Aust. J. Chem. 2004, 57, 1205-1210.
7. (g) Magill, A. M.; Cavell, K. J.; Yates, B. F. J. Am. Chem. Soc. 2004, 126, 8717-8724.
8. (h) Kütt, A.; Leito, I.; Kaljurand, I.; Sooväli, L.; Vlasov, V. M.; Yagupolskii, L. M.; Koppel, I. A. J. Org. Chem. 2006, 71, 2829-2838.
9. (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
10. (b) Wasserscheid, P.; Keim, M. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
11. (c) Rogers, R. D.; Seddon, K. R. Ionic Liquids: Industrial Application to Green Chemistry; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002.
12. (d) Rogers, R. D.; Seddon, K. R. Ionic Liquids as Green Solvents. Progress and Prospects; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003.
13. (e) Rogers, R. D.; Seddon, K. R.; Volkov, S. Green Industrial Application of Ionic Liquids; NATO Science Series II. Mathematics, Physics and Chemistry; Kluwer: Dordrecht, 2003; Vol. 92.
14. (f) Chiappe, C.; Pieraccini, D. J. Phys. Org. Chem. 2005, 18, 275-297.
15. (h) Rogers, R. D.; Seddon, K. R. Ionic Liquids III A: Fundamentals, Progress, Challenges and Opportunities; ACS Symposium Series 901; American Chemical Society: Washington, DC, 2005.
16. (i) Harper, J. B.; Kobrak, M. N. Mini-Rev. Org. Chem. 2006, 3, 253-269.
17. (j) Malhotra, S. V. Ionic Liquids in Organic Synthesis; ACS Symposium Series 950; American Chemical Society: Washington, DC, 2005.
18. (k) Chowdhury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363-2389.
19. (l) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2008.
20. (a) Hanke, C. G.; Johansson, A.; Harper, J. B.; Lynden-Bell, R. M. Chem. Phys. Lett. 2003, 374, 85-90.
21. (b) Holbrey, J. D.; Reichert, W. M.; Nieuwenhuyzen, M.; Sheppard, O.; Hardacre, C.; Rogers, R. D. Chem. Commun. 2003, 476-477.
22. (c) Harper, J. B.; Lynden-Bell, R. M. Mol. Phys. 2004, 102, 85-94.
23. (d) Deetlefs, M.; Hardacre, C.; Nieuwenhuyzen, M.; Sheppard, O.; Soper, A. K. J. Phys. Chem. B 2005, 109, 1573-1598.
24. (e) Lachwa, J.; Bento, I.; Duarte, M. T.; Lopes, J. N. C.; Rebelo, L. P. N. Chem. Commun. 2006, 2445-2447.
25. (f) Lynden-Bell, R. M.; Del Pópolo, M. G.; Youngs, T. G. A.; Kohanoff, J.; Hanke, C. G.; Harper, J. B.; Pinilla, C. C. Acc. Chem. Res. 2007, 40, 1138-1145.
26. (g) Hardacre, C.; Holbrey, J. D.; Nieuwenhuyzen, M.; Youngs, T. G. A. Acc. Chem. Res. 2007, 40, 1146-1155.
27. (a) Dupont, J. J. Braz. Chem. Soc. 2004, 15, 341-350.
28. (b) Gozzo, F. C.; Santos, L. S.; Augusti, R.; Consorti, C. S.; Dupont, J.; Eberlin, M. Chem. - Eur. J. 2004, 10, 6187-6193.
29. D'Anna, F.; Frenna, V.; Noto, R.; Pace, V.; Spinelli, D. J. Org. Chem. 2006, 71, 5144-5150.
30. (a) D'Anna, F.; Frenna, V.; Noto, R.; Pace, V.; Spinelli, D. J. Org. Chem. 2005, 70, 2828-2831.
31. (b) D'Anna, F.; Frenna, V.; Noto, R.; Pace, V.; Spinelli, D. J. Org. Chem. 2006, 71, 9637-9642.
32. (c) D'Anna, F.; Noto, R. Tetrahedron 2007, 63, 11681-11685.
33. (d) Mečiarová, M.; Cigáň, M.; Toma, S.; Gáplovský, A. Eur. J. Org. Chem. 2008, 4408-4411.
34. (a) Brinchi, L.; Germani, R.; Savelli, G. Tetrahedron Lett. 2003, 44, 6583-6585.
35. (b) McNulty, J.; Cheekoori, S.; Nair, J. J.; Larichev, V.; Capretta, A.; Robertson, A. J. Tetrahedron Lett. 2005, 46, 3641-3644.
36. (c) Yoshino, T.; Imori, S.; Togo, H. Tetrahedron 2006, 62, 1309-1317.
37. (d) Mallakpour, S.; Yousefian, H. J. Braz. Chem. Soc. 2007, 18, 1220-1223.
38. Malham, I. B.; Letellier, P.; Turmine, M. Talanta 2008, 77, 48-52.
39. Johnson, K. E.; Pagni, R. M.; Bartmess, J. Monatsh. Chem. Chem. Monthly 2007, 138, 1077-1101.
40. (a) Bordwell, F. G.; Branca, J. C.; Hughes, D. L.; Olmstead, W. N. J. Org. Chem. 1980, 45, 3305-3313.
41. (b) Rodima, T.; Kaljurand, I.; Pihl, A.; Mäemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2002, 67, 1873-1881.
42. (c) Rõõm, E.-I.; Kaljurand, I.; Leito, I.; Rodima, T.; Koppel, I. A.; Vlasov, V. M. J. Org. Chem. 2003, 68, 7795-7799.
43. (d) Erdemgil, F. Z.; S, anli, S.; S, anli, N.; Ozkan, G.; Barbosa, J.; Guiteras, J.; Beltrán, J. L. Talanta 2007, 72, 489-496.
44. (e) Perrin, C. L.; Dong, Y. J. Am. Chem. Soc. 2007, 129, 4490-4497.
45. Thomazeau, C.; Olivier-Barbigou, H.; Magna, L.; Luts, S.; Gilbert, B. J. Am. Chem. Soc. 2003, 125, 5264-5265.
46. The measurement samples have a mole fraction of IL of X ≃ 0.5. On the grounds of our previous reports (see: (a) D'Anna, F.; Frenna, V.; La Marca, S.; Noto, R.; Pace, V.; Spinelli, D. Tetrahedron 2008, 64, 672-680.
47. (b) D'Anna, F.; Marullo, S.; Noto, R. J. Org. Chem. 2008, 73, 6224-6228), we are confident that data collected in the binary mixture can be referred to a partially organized solvent medium, such as neat IL.
48. (a) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
49. (b) Aggarwal, V. K.; Emme, I.; Mereu, A. Chem. Commun. 2002, 1612-1613.
50. (c) Handy, S. T.; Okello, M. J. Org. Chem. 2005, 70, 1915-1918.
51. Lide, D. R. In CRC Handbook of Chemistry and Physics, 80th ed.; CRC Press: London, 1999-2000.
52. MacFarlane, D. R.; Forsyth, S. A. In Ionic Liquids as Green Solvents. Progress and Prospects; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003; pp 264-276.
53. Kobrak, M. N. J. Chem. Phys. 2006, 125, 064502-1-11.
54. Yau, H. M.; Barnes, S. A.; Hook, J. M.; Youngs, T. G. A.; Croft, A. K.; Harper, J. B. Chem, Commun. 2008, 3576-3678.
55. Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 45-92.
56. Crowhurst, L.; Mawdslev, P. R.; Perez-Arlandis, J. M.; Salter. P. A.; Welton, T. Phys. Chem, Chem. Phys. 2003, 5, 2790-2794.
57. Steed, W. J.; Atwood, J. L. In Supramolecular Chemistry; Wiley-VCH: Weinheim 2000; pp 26-28.
58. Anslyn, E. V.; Dougherty, D. A. In Modem Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; p 285.
59. D'Anna, F.; Frenna V.; Pace. V.; Noto, R. Tetrahedron 2006, 62, 1690-1698.
60. Cammarata, L.; Kazarian. S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.
61. Bergeron, R. J.; Channing, M. A. J. Am. Chem. Soc. 1979, 101, 2511-2515.