Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N-phenolate betaine dyes

Green Chemistry

Volumn 7, Issue 5, 2005, Pages 339-351

  Reichardt, Christian ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BETAINE DERIVATIVE; CHEMICAL COMPOUND; DYE; IONIC COMPOUND; PHENOL DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CONFERENCE PAPER; DANGEROUS GOODS; EMPIRICISM; LIQUID; ROOM TEMPERATURE;

EID: 19744376923     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b500106b     Document Type: Conference Paper

References (159)

1. C. Reichardt, Pure Appl. Chem., 2004, 76, 1903-1919.
2. C. Reichardt, Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, 3rd edn., 2003.
3. E. Buncel, R. Stairs and H. Wilson, The Role of the Solvent in Chemical Reactions. Oxford University Press, Oxford, 2003.
4. Handbook of Solvents (+ Solvent Data Base on CD-ROM), ed. G. Wypych, ChemTec Publishing, Toronto, 2001, particularly chapters 17, pp. 1149-1200,
5. G. Wypych, Handbook of Solvents (+ Solvent Data Base on CD-ROM) 20, pp. 1315-1418,
6. and G. Wypych, Handbook of Solvents (+ Solvent Data Base on CD-ROM) 21, pp. 1419-1505.
7. Modern Solvents in Organic Synthesis, ed. P. Knochel, Springer, Berlin, 1999.
8. D. J. Adams, P. J. Dyson and S. J. Tavener, Chemistry in Alternative Reaction Media. Wiley, Chichester, 2004.
9. A. Loupy, in Modern Solvents in Organic Synthesis., ed. P. Knochel, Springer, Berlin, 1999, pp. 153-207.
10. (a) P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice. Oxford University Press, Oxford, 1998;
11. (b) A. S. Matlack, Introduction to Green Chemistry. Marcel Dekker, New York, 2001;
12. (c) W. M. Nelson, Green Solvents for Chemistry - Perspectives and Practice, Oxford University Press, Oxford, 2003, particularly chapter 6.5.8, pp. 168-177.
13. (a) P. A. Grieco, Organic Syntheses in Water. Blackie Academic and Professional, London, 1998;
14. (b) N. Akiya and P. E. Savage, Chem. Rev., 2002, 102, 2725-2750.
15. (a) Handbook of Fluorous Chemistry, ed. J. A. Gladysz, D. P. Curran and I. T. Horváth, Wiley-VCH, Weinheim, 2004;
16. (b) A. Endres and G. Maas, Chem. Unserer Zeit, 2000, 34, 382-393.
17. (a) Chemical Synthesis Using Supercritical Fluids, ed. P. G. Jessop and W. Leitner, Wiley-VCH, Weinheim, 1999;
18. (b) R. Noyori, Chem. Rev., 1999, 99, 353-634;
19. (c) W. Leitner, Acc. Chem. Res., 2002, 35, 746-756;
20. W. Leitner, Chem. Unserer Zeit, 2003, 37, 32-38;
21. (d) Y. Marcus, J. Phys. Org. Chem., 2005, 18, 373-384.
22. (a) D. W. Rooney and K. R. Seddon, in Handbook of Solvents, ed. G. Wypych, ChemTec Publishing, Toronto, and William Andrew Publishing, New York, 2001, chapter 21.2, p. 1459-1484;
23. (b) Ionic-Liquids in Synthesis, ed. P. Wasserscheid and T. Welton, Wiley-VCH, Weinheim, 2003;
24. (c) P. Wasserscheid, Chem. Unserer Zeit, 2003, 37, 52-63;
25. (d) C. Chiappe and D. Pieraccini, J. Phys. Org. Chem., 2005, 18, 275-297.
26. S. Sankararaman and J. E. Nesakumar, Eur. J. Org. Chem., 2000, 2003-2011.
27. R. Fuoss, J. Chem. Educ., 1955, 32, 527.
28. (a) P. Walden, Bull. Acad. Imp. Sci. St.-Petersbourg, 1914, 8, 405-422,
29. Chem. Zentralbl, 1914, 1800;
30. (b) See also: S. Sugden and H. Wilkins, J. Chem. Soc., 1929, 1291-1298;
31. (c) D. F. Evans, A. Yamauchi, R. Roman and E. Z. Casassa, J. Colloid Interface Sci, 1982, 88, 89-96;
32. (d) D. Mirejowski and E. M. Arnett, J. Am. Chem. Soc., 1983, 105, 1112-1117;
33. (e) D. A. Jaeger and C. E. Tucker, Tetrahedron Lett., 1989, 30, 1785-1788.
34. P. C. Ray and J. N. Rakshit, J. Chem. Soc., 1911, 1470-1475.
35. (a) W. Sundermeyer, Angew. Chem., 1965, 77, 241-258,
36. Angew. Chem., Int. Ed. Engl., 1976, 4, 222-238;
37. (b) W. Sundermeyer, Chem. Unserer Zeit, 1967, 1, 150-157.
38. Ionic Liquids, ed. D. Inman and D. G. Lovering, Plenum Press, New York, 1981.
39. C. F. Poole, J. Chromatogr. A, 2004, 1037, 49-82.
40. C. G. Swain, A. Ohno, D. K. Roe, R. Brown and T. Maugh, J. Am. Chem. Soc., 1967, 89, 2648-2649.
41. (a) F. H. Hurley and T. P. Wier, J. Electrochem. Soc., 1961, 98, 203-206;
42. (b) H. L. Chum, V. R. Koch, L. L. Miller and R. A. Osteryoung, J. Am. Chem. Soc., 1975, 97, 3264-3265.
43. (a) J. S. Wilkes, J. A. Levisky, R. A. Wilson and C. L. Hussey, Inorg. Chem., 1982, 21, 1263-1264;
44. (b) J. R. Sanders, E. H. Ward and C. L. Hussey, Proc. Electrochem. Soc., 1986, 86-1, 307-316,
45. Chem. Abstr., 1986, 104, 156804s, special issue on molten salts;
46. (c) J. S. Wilkes and M. J. Zaworotko, J. Chem. Soc., Chem. Commun., 1992, 965-967.
47. P. Wasserscheid and W. Keim, Angew. Chem., 2000, 112, 3926-3945,
48. Angew. Chem., Int. Ed., 2000, 39, 3772-3789.
49. (a) N. L. Lancaster, T. Welton and G. B. Young, J. Chem. Soc., Perkin Trans. 2, 2001, 2267-2270;
50. (b) N. L. Lancaster, P. A. Salter, T. Welton and G. B. Young, J. Org. Chem., 2002, 67, 8855-8861;
51. (c) N. L. Lancaster and T. Welton, J. Org. Chem., 2004, 69, 5986-5992;
52. (d) L. Crowhurst, N. L. Lancaster, J. M. Pérez Arlandis and T. Welton, J. Am. Chem. Soc., 2004, 126, 11549-11555;
53. (e) C. Chiappe, D. Pieraccini and P. Saullo, J. Org. Chem., 2003, 68, 6710-6715.
54. C. Reichardt, Angew. Chem., 1965, 77, 30-40,
55. Angew. Chem., Int. Ed. Engl., 1965, 4, 29-40.
56. P. Müller, Pure Appl. Chem., 1994, 66, 1077-1184, particularly p. 1151.
57. A. Streitwieser, C. H. Heathcock and E. M. Kosower, Introduction to Organic Chemistry, MacMillan Publishing Company, New York, 4th edn., 1992, p. 677 ff. and Essay 4.
58. (a) L. P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, 2nd edn., 1970;
59. L. P. Hammett, Physikalische Organische Chemie., Verlag Chemie, Weinheim, 1973, p. 352 ff;
60. (b) J. Shorter, Chem. Unserer Zeit, 1985, 19, 197-208.
61. T used in photochemistry as abbreviation for triplet energy.
62. (a) C. Reichardt, Chem. Soc. Rev., 1992, 21, 147-153;
63. (b) C. Reichardt, Chem. Rev., 1994, 94, 2319-2358.
64. A. Schweig and C. Reichardt, Z. Naturforsch., Part A, 1966, 21a, 1373-1376, value for 2,6-di-t-butyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate for solubility reasons.
65. R. Allmann, Z. Kristallogr., 1969, 128, 115-132.
66. W. Liptay, Z. Naturforsch., A, 1965, 20, 1441-1471;
67. W. Liptay, Z. Naturforsch., A, 1966, 21, 1605-1618.
68. (a) M. C. Beard, G. M. Turner and C. A. Schmuttenmaer, J. Am. Chem. Soc., 2000, 122, 11541-11542;
69. (b) C. A. Schmuttenmaer, Chem. Rev., 2004, 104, 1759-1779, particularly p. 1769.
70. (a) H. Langhals, Angew. Chem., 1982, 94, 739-749;
71. Angew. Chem., Int. Ed. Engl., 1982, 21, 724-733;
72. (b) R. D. Skwierczynski and K. A. Connors, J. Chem. Soc., Perkin Trans. 2, 1994, 467-472;
73. (c) M. Rosés, C. Ráfols, J. Ortega and E. Bosch, J. Chem. Soc., Perkin Trans. 2, 1995, 1607-1615;
74. M. Rosés, C. Ráfols, J. Ortega and E. Bosch, J. Chem. Soc., Perkin Trans. 2, 1996, 1497-1503;
75. E. Bosch, F. Rived and M. Rosés, J. Chem. Soc., Perkin Trans. 2, 1996, 2177-2184;
76. C. Ráfols, M. Rosés and E. Bosch, J. Chem. Soc., Perkin Trans. 2, 1997, 243-248;
77. M. Rosés, U. Buhvestov, C. Ráfols, F. Rived and E. Bosch, J. Chem. Soc., Perkin Trans. 2, 1997, 1341-1348.
78. D. A. Johnson, R. Shaw and E. F. Silversmith, J. Chem. Educ., 1994, 71, 517.
79. B. R. Osterby and R. D. McKelvey, J. Chem. Educ., 1996, 73, 260-261.
80. T. Deng and W. E. Acree, Jr., J. Chem. Educ., 1999, 76, 1555-1556.
81. M. F. Vitha, J. Chem. Educ., 2001, 78, 370-372.
82. C. Machado and V. G. Machado, J. Chem. Educ., 2001, 78, 649-651.
83. C. Reichardt and E. Harbusch-Görnert, Liebigs Ann. Chem., 1983, 721-743.
84. (a) C. Reichardt, Angew. Chem., 1979, 91, 119-131;
85. Angew. Chem., Int. Ed. Engl., 1979, 18, 98-110;
86. (b) O. Exner, Correlation Analysis of Chemical Data. Plenum Press, New York, 1988.
87. (a) C. Reichardt, D. Che, G. Heckenkemper and G. Schäfer, Eur. J. Org. Chem., 2001, 2343-2361;
88. (b) C. Reichardt, M. Eschner and G. Schäfer, J. Phys. Org. Chem., 2001, 14, 737-751.
89. A. J. Parker, Q. Rev. Chem. Soc., 1962, 16, 163-187;
90. A. J. Parker, Adv. Org. Chem., 1965, 5, 1-46;
91. A. J. Parker, Adv. Phys. Org. Chem., 1967, 5, 173-235;
92. A. J. Parker, Chem. Rev., 1969, 69, 1-32.
93. (a) W. Schroth, H.-D. Schädler and J. Andersch, Z. Chem., 1989, 29, 56-57;
94. (b) W. Schroth, J. Andersch, H.-D. Schädler and R. Spitzner, Chem.-Ztg., 1989, 113, 261-271.
95. (a) S. K. Poole, P. H. Shetty and C. F. Poole, Anal. Chim. Acta, 1989, 218, 241-264:
96. (b) C. F. Poole, J. Chromatogr., Part A, 2004, 1037, 49-82.
97. W. B. Harrod and N. J. Pienta, J. Phvs. Org. Chem., 1990, 3, 534-544.
98. I.-M. Herfort and H. Schneider, Liebigs Ann. Chem., 1991, 27-31.
99. E. Bart, A. Meltsin and D. Huppert, J. Phys. Chem., 1994, 98, 3295-3299.
100. (a) P. Wasserscheid, C. M. Gordon, C. Hilgers, M. J. Muldoon and I. R. Dunkin, J. Chem. Soc., Chem. Commun., 2001, 1186-1187;
101. (b) M. J. Muldoon, C. M. Gordon and I. R. Dunkin, J. Chem. Soc., Perkin Trans. 2, 2001, 433-435.
102. (a) K. A. Fletcher, I. A. Storey, A. E. Hendricks, Sh. Pandey and Si. Pandey, Green Chem., 2001, 3, 210-215;
103. (b) K. A. Fletcher and S. Pandey, Appl. Spectrosc., 2002, 56, 266-271;
104. (c) K. A. Fletcher and S. Pandey, Appl. Spectrosc., 2002, 56, 1498-1503;
105. (d) S. N. Baker, G. A. Baker and F. V. Bright, Green Chem., 2002, 4, 165-169;
106. (e) K. A. Fletcher and S. Pandey, Proc. Electrochem. Soc., 2002, 19, 244-256,
107. Chem. Abstr., 2003, 139, 266433, special issue on molten salts;
108. (f) K. A. Fletcher, S. N. Baker, G. A. Baker and S. Pandey, New J. Chem., 2003, 27, 1706-1712;
109. (g) K. A. Fletcher and S. Pandey, J. Phys. Chem. B, 2003, 107, 13532-13539.
110. (a) S. N. V. K. Aki, J. F. Brennecke and A. Samanta, J. Chem. Soc., Chem. Commun., 2001, 413-414;
111. (b) R. Karmakar and A. Samanta, J. Phys. Chem. A, 2002, 106, 4447-4452;
112. (c) R. Karmakar and A. Samanta, J. Phys. Chem. A, 2003, 107, 7340-7346;
113. (d) S. Saha, P. K. Mandal and A. Samanta, Phys. Chem. Chem. Phys., 2004, 6, 3106-3110;
114. (e) A. Samanta, personal communication, University of Hyderabad, 2004;
115. (f) C. P. Fredlake, M. J. Muldoon, S. N. V. K. Aki, T. Welton and J. F. Brennecke, Phys. Chem. Chem. Phys., 2004, 6, 3280-3285.
116. S. Park and R. J. Kazlauskas, J. Org. Chem., 2001, 66, 8395-8401.
117. J. G. Huddleston, G. Broker, H. Willauer and R. D. Rogers, in Ionic Liquids - Industrial Applications for Green Chemistry, ed. R. D. Rogers and K. Seddon, American Chemical Society, Washington, DC, 2002, pp. 270-288.
118. (a) S. V. Dzyuba and R. A. Bartsch, Tetrahedron Lett., 2002, 43, 4657-4659;
119. (b) S. V. Dzyuba and R. A. Bartsch, Chem. Phys. Chem., 2002, 3, 161-166;
120. (c) R. A. Bartsch and S. V. Dzyuba, in: Ionic Liquids as Green Solvents - Progress and Prospects, American Chemical Society, Washington, DC, 2003, p. 289-299;
121. Chem. Abstr., 2004, 140, 253495.
122. J. L. Kaar, A. M. Jesionowski, J. A. Berberich, R. Moulton and A. J. Russel, J. Am. Chem. Soc., 2003, 125, 4125-4131.
123. J. A. Ingram, R. S. Moog, N. Ito, R. Biswas and M. Maroncelli, J. Phys. Chem. B, 2003, 107, 5926-5932.
124. V. Znamenskiy and M. N. Kobrak, J. Phys. Chem. B, 2004, 108, 1072-1079.
125. (a) T. Welton, in Ionic Liquids in Synthesis, ed. P. Wasserscheid and T. Welton, Wiley-VCH, Weinheim, 2003, p. 94-99, (particularly Table 3.5-1 on p. 97);
126. (b) L. Crowhurst, P. R. Mawdsley, J. M. Perez-Arlandis, P. A. Salter and T. Welton, Phys. Chem. Chem. Phys., 2003, 5, 2790-2794.
127. (a) C. Chiappe, P. Piccioli, D. Pieraccini, P. De Maria and G. Siani, poster presented at Green Solvents for Synthesis, Bruchsal, Germany, October 3-6, 2004;
128. (b) C. Chiappe, personal communication, Pisa, October 18, 2004.
129. (a) A. J. Carmichael and K. R. Seddon, J. Phys. Org. Chem., 2000, 13, 591-595;
130. (b) W. Ogihara, T. Aoyama and H. Ohno, Chem. Lett., 2004, 33, 1414-1415.
131. P. Bonhote, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram and M. Grätzel, Inorg. Chem., 1996, 35, 1168-1178.
132. V. Znamenskiy and M. N. Kobrak, J. Phys. Chem. B, 2004, 108, 1072-1079.
133. (a) M. G. Del Pópolo and G. A. Voth, J. Phys. Chem. B, 2004, 108, 1744-1754;
134. (b) W. Schröer and H. Weingärtner, Pure Appl. Chem., 2004, 76, 19-27.
135. (a) A. Elaiwi, P. B. Hitchcock, K. R. Seddon, N. Srinivasan, Y.-M. Tan, T. Welton and J. A. Zora, J. Chem. Soc., Dalton Trans., 1995, 3467-3472;
136. (b) J. Ross and J. Xiao, Chem. Eur. J., 2003, 9, 4900-4906;
137. (c) J. Dupont, J. Braz. Chem. Soc., 2004, 15, 341-350, and references cited in these papers.
138. Recent review on stable singlet-diaminocarbenes: W. Kirmse, Angew. Chem., 2004, 116, 1799-1801,
139. Angew. Chem., Int. Ed.., 2004, 43, 1767-1769.
140. (a) V. K. Aggarwal, J. Emme and A. Mereu, J. Chem. Soc., Chem. Commun., 2002, 1612-1613;
141. (b) J.-C. Hsu, Y.-H. Yen and Y.-H. Chu, Tetrahedron Lett., 2004, 45, 4673-4767.
142. J. L. Anderson, J. Ding, T. Welton and D. W. Armstrong, J. Am. Chem. Soc., 2002, 124, 14247-14254.
143. K. Swiderski, A. McLean, C. M. Gordon and D. H. Vaughan, J. Chem. Soc., Chem. Commun., 2004, 2178-2179.
144. Y. U. Paulechka, G. J. Kabo, A. V. Blokhin, O. A. Vydrov, J. W. Magee and M. Frenkel, J. Chem. Eng. Data, 2003, 48, 457--462.
145. V. Gutmann, The Donor-Acceptor Approach to Molecular Interactions. Plenum, New York, 1978.
146. (a) T. M. Krygowski and W. R. Fawcett, J. Am. Chem. Soc., 1975, 97, 2143-2148;
147. Aust. J. Chem., 1975, 28, 2115-2124;
148. Can. J. Chem., 1976, 54, 3283-3292;
149. (b) W. R. Fawcett, J. Phys. Chem., 1993, 97, 9540-9546;
150. (c) W. R. Fawcett, Liquids, Solutions, and Interfaces - From Classical Macroscopic Descriptions to Modern Microscopic Details. Oxford University Press, Oxford, 2004, ch. 4.9, p. 191 ff.
151. (a) M. J. Kamlet, J.-L. M. Abboud and R. W. Taft, J. Am. Chem. Soc., 1977, 99, 6027-6038, 8325-8327;
152. (b) J.-L. M. Abboud, M. J. Kamlet and R. W. Taft, Prog. Phys. Org. Chem., 1981, 13, 485-630;
153. (c) M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham and R. W. Taft, J. Org. Chem., 1983, 48, 2877-2887;
154. (d) R. W. Taft, J.-L. M. Abboud, M. J. Kamlet and M. H. Abraham, J. Solution Chem., 1985, 14, 153-186.
155. C. Laurence, P. Nicolet, M. T. Dalati, J.-L. M. Abboud and R. Notario, J. Chem. Phys., 1994, 98, 5807-5816.
156. Y. Marcus, Chem. Soc. Rev., 1993, 22, 409-416.
157. (a) Y. Marcus, The Properties of Solvents. Wiley, Chichester, 1998, particularly Table 4.3 on p. 145 ff;
158. (b) J.-L. M. Abboud and R. Notario, Pure Appl. Chem., 1999, 71, 645-718.
159. A. Kawai, T. Hidemori and K. Shibuya, Chem. Lett., 2004, 33, 1464-1465.