Raman spectroscopic study on solvation of diphenylcyclopropenone and phenol blue in room temperature ionic liquids

Journal of Physical Chemistry A

Volumn 110, Issue 18, 2006, Pages 6164-6172

  Fujisawa, Tomotsumi ^a   Fukuda, Masanori ^a   Terazima, Masahide ^a   Kimura, Yoshifumi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; ACIDITY; BANDWIDTH; METHANOL; ORGANIC SOLVENTS; RAMAN SPECTROSCOPY;

ACCEPTOR NUMBERS (AN); DIPHENYLCYCLOPROPENONE (DPCP); LEWIS ACIDITY;

PHENOLS;

EID: 33744805066     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp057423d     Document Type: Article

References (68)

1. Welton, T. Chem. Rev. 1999, 99, 2071.
2. Ionic liquids: The Front and Future of Material Development; Ohno, H., Ed.; CMC: Tokyo, Japan, 2002.
3. Ionic Liquids in Synthesis; Welton, T., Ed.; Willy-VCH-Verlag: Weinheim, Germany, 2003.
4. Buzzeo, M. C.; Evans, R. G.; Compton, R. G. ChemPhysChem. 2004, 5, 1106.
5. Poole, C. F. J. Chromatogr. A 2004, 1037, 49.
6. Ue, M.; Takeda, M.; Toriumi, A.; Kominato, A.; Hagiwara, R.; Ito, Y. J. Electrochem. Soc. 2005, 150 (4), A499.
7. Weingartner, H.; Knocks, A.; Schrader, W.; Kaatze, U. J. Phys. Chem. A 2001, 105, 8646.
8. Paul, A.; Mandal, P. K.; Samanta, A. Chem. Phys. Lett. 2005, 402, 375.
9. Liu, J.; Jonsson, J. A.; Jiang, G. Trends Anal. Chem. 2005, 24, 20.
10. Ozawa, R.; Hayashi, S.; Saha, S.; Kobayashi, A.; Hamaguchi, H. Chem. Lett. 2003, 32, 948.
11. Hamaguchi, H.; Ozawa, R.; Hayashi, S.; Satyen, S. Abstract of Papers, 226th National Meeting of the American Chemical Society; American Chemical Scoiety: Washington, DC, 2003; U622.
12. Katayanagi, H.; Hayashi, S.; Hamaguchi, H.; Nishikawa, K. Chem. Phys. Lett. 2004, 392, 460.
13. Hamaguchi, H.; Ozawa, R. Adv. Phys. Chem. 2005, 131, 85.
14. Hyun, B. R.; Dzyuba, S. V.; Bausch, R. A.; Quitevis, E. L. J. Phys. Chem. A 2002, 106, 7579.
15. Valkenburg, M. E. V.; Vaughn, R. L.; Williams, M.; Wilkes, J. S. Themochim. Acta 2005, 425, 181.
16. Crowhurst, L.; Mawdsley, P. R.; Perez-Arlandis, J. M.; Slater, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2003, 5, 2790.
17. Fletcher, K. A.; Storey, I. A.; Hendricks, A. E.; Pandey, S.; Pandey, S. Green Chem. 2001, 3, 210.
18. Baker, S. N.; Baker, G. A.; Bright, F. V. Green Chem. 2002, 4, 165.
19. Dzyuba, S. V.; Bartsch, R. A. Tetrahedron Lett. 2002, 43, 4657.
20. Taft, R. W.; Kamlet, M. J. J. Am. Chem. Soc. 1976, 98, 2886.
21. Kamlet, M. J.; Abboud, J. L.; Taft, R. W. J. Am. Chem. Soc. 1977, 99, 6027.
22. Reichardt, C. Chem. Rev. 1994, 94, 2319.
23. Karmakar, R.; Samanta, A. J. Phys. Chem. A 2002, 106, 6670.
24. Karmakar, R.; Samanta, A. J. Phys. Chem. A 2002, 106, 4447.
25. Saha, S.; Mandal, P. K.; Samanta, A. Phys. Chem. Chem. Phys. 2004, 6, 3106.
26. Chowdhury, P. K.; Halder, M.; Sanders, L.; Calhoun, T.; Anderson, J. L.; Armstrong, D. W.; Song, X.; Petrich, J. W. J. Phys. Chem. B 2004, 108, 10245.
27. Ito, N.; Arzhantsev, S.; Heitz, M.; Maroncelli, M. J. Phys. Chem. B 2004, 108, 5771.
28. Arzhantsev, S.; Ito, N.; Heitz, M.; Maroncelli, M. Chem. Phys. Lett. 2003, 381, 278.
29. Ito, N.; Arzhantsev, S.; Maroncelli, M. Chem. Phys. Lett. 2004, 596, 83.
30. Charkrabarty, D.; Hazra, P.; Chakraborty, A.; Seth, D.; Sarkar, N. Chem. Phys. Lett. 2003, 381, 697.
31. Mandal, P. K.; Sarkar, M.; Samanta, A. J. Phys. Chem. A 2004, 108, 9048.
32. Ammon, H. L. J. Am. Chem. Soc. 1973, 17, 7093.
33. Gomaa, M. A.-M. J. Chem. Soc., Perkin Trans. 1 2002, 341.
34. Terazima, M.; Hara, T.; Hirota, N. Chem. Phys. Soc. 1995, 246, 577.
35. Takeuchi, S.; Tahara, T. J. Chem. Phys. 2004, 120, 4768.
36. Osawa, E.; Kitamura, K.; Yoshida, Z. J. Am. Chem. Soc. 1967, 89, 3814.
37. Almeida, L. C. J.; Santos, P. S. Spectrochim. Acta 2002, 58, 3139.
38. Kimura, Y.; Fukuda, M.; Fujisawa, T.; Terazima, M. Chem. Lett. 2005, 34, 338.
39. See, e.g.: Reichardt, C. Solvents and Solvents effects in Organic Chemistry; VCH: Weinheim, Germany, 1988.
40. Figueras, J. J. Am. Chem. Soc. 1971, 93, 3255.
41. Yamaguchi, T.; Kimura, Y.; Hirota, N. J. Phys. Chem. A 1997, 101, 9050.
42. Yamaguchi, T.; Kimura, Y.; Hirota, N. J. Chem. Phys. 1997, 107, 4436.
43. Yamaguchi, T.; Kimura, Y.; Hirota, N. J. Chem. Phys. 1998, 109, 9075.
44. Yamaguchi, T.; Kimura, Y.; Hirota, N. J. Chem. Phys. 1998, 109, 9084.
45. Morley, J. O.; Fitton, A. L. J. Phys. Chem. A 1999, 103, 11442.
46. Nagasawa, Y.; Watanabe, A.; Ando, Y.; Okada, T. J. Mol. Liq. 2001, 90, 295.
47. Chen, J.; Shen, D.; Wu, W.; Han, B.; Wang, B.; Sun, D. J. Chem. Phys. 2005, 122, 204508.
48. Huddleston, J. G.; Wilauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 16, 1765.
49. Holbrey J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133.
50. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192.
51. Dupont, J.; Consorti, C. S.; Suarez, P. A. Z.; de Souza, R. F. Org. Synth. 2003, 79, 236.
52. Marcus, Y. Chem. Soc. Rev. 1993, 22, 409.
53. 48
54. 4] was not measured due to strong fluorescence from the solvent.
55. Headley, A. D.; Jackson, N. M. J. Phys. Org. Chem. 2002, 15, 52.
56. Antony, J. H.; Mertens, D.; Dolle, A.; Wasserscheid, P.; Carper, W. R. ChemPhysChem 2003, 4, 588.
57. Kolling, O. W. Anal. Chem. 1981, 53, 54.
58. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877.
59. Ulstrup, J.; Jortner, J. J. Chem. Phys. 1975, 63, 4358.
60. Sakaebe, H.; Matsumoto, H. Electrochem. Commun. 2003, 5, 594.
61. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, Md. A. B. H.; Watanabe, M. J. Phys. Chem. B 2004, 108, 16593.
62. Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156.
63. Gu, Z.; Brennecke, J. F. J. Chem. Eng. Data. 2002, 47, 339.
64. Fredlake, C. P.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. J. Chem. Eng. Data 2004, 49, 954.
65. Kim, Y.-J.; Matsuzawa, Y.; Ozaki, S.; Park, K. C.; Kim, C.; Endo, M.; Yoshida, H.; Masuda, G.; Sato, T.; Dresselhaus, S. D. J. Electrochem. Soc. 2005, 152, A710.
66. -3 at 25°C.
67. MacRae, E. G. J. Phys. Chem. 1957, 61, 562.
68. -1 relative to cyclohexane, which explains the larger absorption shift to some extent.