Designing ionic liquids: 1-Butyl-3-methylimidazolium cations with substituted tetraphenylborate counterions

European Journal of Inorganic Chemistry

Volumn , Issue 15, 2003, Pages 2798-2811

  Van den Broeke, Joep ^a   Stam, Marjolijn ^a   Lutz, Martin ^b   Kooijman, Huub ^b   Spek, Anthony L ^b   Deelman, Berth Jan ^c   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c ARKEMA   (France)

Author keywords

Anions; Cations; Hydrogen bonds; Ionic liquids; X ray diffraction

Indexed keywords

CRYSTAL STRUCTURE; HYDROGEN BONDS; MELTING; NEGATIVE IONS; POSITIVE IONS; SALTS; SINGLE CRYSTALS; X RAY DIFFRACTION;

COUNTERIONS; HYDROPHOBICS; IMIDAZOLIUM; LOW MELTING; METHYLIMIDAZOLIUM SALTS; SINGLE CRYSTAL X-RAY STRUCTURES; SYSTEMATIC VARIATION; TETRAPHENYLBORATES; X- RAY DIFFRACTIONS; X-RAY STRUCTURE DETERMINATIONS;

IONIC LIQUIDS;

1 BUTYL 3 METHYLIMIDAZOLIUM CATION; BORANE DERIVATIVE; CARBENE TRIS[4 [DIMETHYL (3,3,3 TRIFLUOROPROPYL)SILYL]PHENYL]BORANE; IMIDAZOLE DERIVATIVE; TETRAPHENYLBORON; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; HYDROGEN BOND; HYDROPHOBICITY; INFRARED SPECTROSCOPY; LIPOPHILICITY; MELTING POINT; NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 0043237712     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300057     Document Type: Article

References (94)

1. For recent reviews see: [1a] J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3691.
2. [1b] H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A 2002, 182-183, 419-437.
3. [1c] R. Sheldon, Chem. Commun. 2001, 2399-2407.
4. [1d] P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772-3789.
5. [1e] P. Wasserscheid, W. Keim, Angew. Chemie 2000, 112, 3926-3945.
6. [1f] T. Welton, Chem. Rev. 1999, 99, 2071-2083.
7. [2a] P. T. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694.
8. [2b] K. R. Seddon, J. Chem. Tech. & Biotech. 1997, 68, 351-356.
9. [2c] European Union Council Directive 1999/13/EG of 11 March 1999, Official Journal L85, 29.03.1999.
10. [2d] Clean Air Act and Amendments, 42 U. S. C. 7401, et seq.
11. [3a] P. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzel, Inorg. Chem. 1996, 35, 1168-1178.
12. [3b] H. Waffenschmidt, PhD Thesis, RWTH Aachen, Germany, 2000.
13. J. S. Wilkes, M. J. Zaworotko, J. Chem. Soc., Chem. Commun. 1992, 965-966.
14. [5a] A. S. Larsen, J. D. Holbrey, F. S. Tham, C. A. Reed, J. Am. Chem. Soc. 2000, 122, 7264-7272.
15. [5b] D. R. MacFarlane, J. Golding, S. Forsyth, M. Forsyth, G. B. Deacon, Chem. Commun. 2001, 1430-1431.
16. [5c] S. V. Dzyuba, R. A. Bartsch, Chem. Commun. 2001, 1466-1467.
17. [5d] T. L. Merrigan, E. D. Bates, S. C. Dorman, J. H. Davis, Chem. Commun. 2000, 2051-2052.
18. [5e] J. H. Davis, K. J. Forrester, Tetrahedron Lett. 1999, 40, 1621-1622.
19. [5f] L. C. Branco, J. N. Rosa, J. J. Moura Ramos, C. A. M. Afonso, Chem. Eur J. 2002, 8, 3671-3677.
20. [6a] R. Hagiwara, Y. Ito, J. Fluorine Chem. 2000, 105, 221-227.
21. [6b] S. V. Dzyuba, R. A. Bartsch, Chem. Phys. Chem. 2002, 3, 161-166.
22. [6c] J. Sun, M. Forsyth, D. R. MacFarlane, J. Phys. Chem. B 1998, 102, 8858-8864.
23. [6d] J. D. Holbrey, K. R. Seddon, J. Chem. Soc., Dalton Trans. 1999, 2133-2140.
24. [6e] J.-F. Huang, P.-Y. Chen, I.-W. Sun, S. P. Wang, Inorg. Chim. Acta 2001, 320, 7-11.
25. [6f] A. D. Headley, N. M. Jackson, J. Phys. Org. Chem. 2002, 15, 52-55.
26. [6g] K. R. Seddon, A. Stark, M.-J. Torres, Pure Appl. Chem. 2000, 72, 2275-2287.
27. [7a] P. A. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. de Souza, J. Dupont, Polyhedron 1996, 15, 1217-1219.
28. [7b] Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. Int. Ed. Engl. 1996, 34, 2698-2700.
29. [7c] C. M. Gordon, Appl. Catal. A 2001, 222, 101-117.
30. [7d] W. Keim, D. Vogt, H. Waffenschmidt, P. Wasserscheid, J. Catal. 1999, 186, 481-484.
31. [7e] A. Bösmann, G. Franciò, E. Janssen, M. Solinas, W. Leitner, P. Wasserscheid, Angew. Chem. Int. Ed. 2001, 40, 2697-2699.
32. [7f] M. F. Sellin, P. B. Webb, D. J. Cole-Hamilton, Chem. Commun. 2001, 781-782.
33. [7g] P. Lozano, T. De Diego, D. Carrié, M. Vaultier, J. L. Iborra, Chem. Commun. 2002, 692-693.
34. J. DuPont, P. A. Z. Suarez, R. F. De Souza, R. A. Burrow, J.-P. Kintzinger, Chem. Eur. J. 2000, 6, 2377-2381.
35. S. H. Strauss, Chem. Rev. 1993, 93, 927-942.
36. C. A. Reed, Acc. Chem. Res. 1998, 31, 133-139.
37. L. Cammarata, S. G. Kazarian, P. A. Salter, T. Welton, Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.
38. J. van den Broeke, F. Winter, B.-J. Deelman, G. van Koten, Org. Lett. 2002, 4, 3851-3854.
39. P. W. Glunz, S. Hintermann, L. J. Williams, J. B. Schwarz, S. C. Kuduk, V. Kudryashov, K. O. Lloyd, S. J. Danishefsky, J. Am. Chem. Soc. 2000, 122, 7273-7279.
40. A. Elaiwi, P. B. Hitchcock, K. R. Seddon, N. Srinivasan, Y.-M. Tan, T. Welton, J. A. Zora, J. Chem. Soc., Dalton Trans. 1995, 3467-3472.
41. J. van den Broeke, M. Lutz, H. Kooijman, A. L. Spek, B.-J. Deelman, G. van Koten, Organometallics 2001, 20, 2114-2117.
42. [16a] G. R. Desiraju, T. Steiner, in The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
43. [16b] J. F. Malone, C. M. Murray, M. H. Charlton, R. Docherty, A. J. Lavery, J. Chem. Soc., Faraday Trans. 1997, 93, 3429-3436.
44. [17a] M. Nishio, M. Hirote, Y. Umezawa, in The CH/π Interaction Evidence, Nature and Consequences; John Wiley & Sons, New York, 1998.
45. [17b] I. Alkorta, I. Rozas, J. Elguero, Chem. Soc. Rev. 1998, 27, 163-170.
46. [17c] S. Harder, Chem. Eur. J. 1999, 5, 1852-1861.
47. [18a] V. R. Thalladi, H.-C. Weiss, D. Bläser, R. Boese, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 8702-8710.
48. [18b] J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89-98.
49. [19a] M.-A. Guillevic, A. M. Arif, I. T. Horváth, J. A. Gladysz, Angew. Chem. Int. Ed. Engl. 1997, 36, 1612-1615.
50. [19b] E. de Wolf, A. L. Spek, B. W. M. Kuipers, A. P. Philipse, J.D. Meeldijk, P. H. H. Bomans, P. M. Frederik, B.-J. Deelman, G. van Koten, Tetrahedron 2002, 58, 3911-3922.
51. [19c] R. P. Singh, B. Twamley, J. M. Shreeve, J. Chem. Dalton Trans. 2000, 4089-4092.
52. [19d] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-99.
53. Chemical shifts for tetraphenylboron compounds can be observed between δ = 0 ppm and -25 ppm: [20a] J. D. Kennedy, in Multinuclear NMR; (Ed.: J. Mason); Plenum Press: New York, 1987, 221. [20b] H. Nöth, H. Vahrenkamp, Chem. Ber. 1966, 99, 1049-1067.
54. Chemical shifts for tetraphenylboron compounds can be observed between δ = 0 ppm and -25 ppm: [20a] J. D. Kennedy, in Multinuclear NMR; (Ed.: J. Mason); Plenum Press: New York, 1987, 221. [20b] H. Nöth, H. Vahrenkamp, Chem. Ber. 1966, 99, 1049-1067.
55. [21a] W. Baratta, E. Herdtweck, W. A. Herrmann, P. Rigo, J. Schwarz, Organometallics 2002, 21, 2101-2106.
56. [21b] S. Caddick, F. G. N. Cloke, G. K. B. Clentsmith, P. Hitchcock, D. McKerrecher, L. R. Titcomb, M. R. V. Williams, J. Organomet. Chem. 2001, 617-618, 635-639.
57. [21c] A. J. Arduengo, S. F. Gamper, J. C. Calabrese, F. Davidson, J. Am. Chem. Soc. 1994, 116, 4391-4394.
58. [21d] A. J. Arduengo, H. V. R. Dias, F. Davidson, R. L. Harlow, J. Organomet. Chem. 1993, 462, 13-18.
59. N. Kuhn, G. Henkel, T. Kratz, J. Kreuzenberg, R. Boese, A. H. Maulitz, Chem. Ber. 1993, 126, 2041-2045.
60. L. Weber, E. Dobbert, H.-G. Stammler, B. Neumann, R. Boese, D. Bläser, Chem. Ber./Recueil 1997, 130, 705-710.
61. D. S. Otkidach, I. V. Pletnev, Theochem. 2001, 536, 65-72.
62. [25a] P. Haake, L. P. Bausher, J. Phys. Chem. 1968, 78, 2213-2217.
63. [25b] A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363.
64. [25c] A. J. Arduengo, H. V. R. Dias, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1992, 114, 5530-5534.
65. T. V. Ashworth, M. J. Nolte, R. H. Reimann, E. Singleton, J. Chem. Soc., Chem. Commun. 1977, 936-937.
66. D. S. McGuinness, K. J. Cavell, B. F. Yates, B. W. Skelton, A. H. White, J. Am. Chem. Soc. 2001, 123, 8317.
67. [28a] M. Koel, Proc. Estonian Acad. Sci. Chem. 2000, 49, 145-155.
68. [28b] P. A. Z. Suarez, S. Einloft, J. E. L. Dullius, R. F. de Souza, J. Dupont, J. Chem. Phys. 1998, 95, 1626-1639.
69. S. Bratos, H. Ratajczak, P. Voit, in Mathematical and Physical Sciences, (Eds.: J. C. Dore, J. Teixeira), NATO ASI Ser. C, Kluwer: Dordrecht, 1989, vol. 329, p. 221.
70. C. G. Hanke, N. A. Atamas, R. M. Lynden-Bell, Green Chem. 2002, 4, 107-111.
71. [31a] M. Hesse, H. Meier, B. Zeeh, in Spektroskopische Methoden in der Organischen Chemie, 2nd ed.; Thieme Verlag: Stuttgart, Germany, 1984.
72. [31b] J. W. Akitt, in NMR and Chemistry: an Introduction to the Fourier Transform-Multinuclear Era, 2nd ed.; Chapman and Hall: London, 1983.
73. A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon, T. Welton, Proceedings of the 8th International Symposium on Molten Salts; The Electrochemical Society: Pennington, NJ, 1992; Proceeding Vol. 92-16, p. 98.
74. During repeated heating cycles, a slight change in the slope of the DSC trace could be observed at these temperatures.
75. 2- linker facilitates a high degree of freedom in the orientation of the attached alkyl- and perfluoroalkyl groups.
76. H. Bock, T. T. H. Van, H. Schödel, J. Prak. Chem. 1997, 339, 525-533.
77. [36a] A. J. Carmichael, K. R. Seddon, J. Phys. Org. Chem. 2000, 13, 591-595.
78. [36b] K. A. Fletcher, I. A. Storey, A. E. Hendricks, S. Pandey, S. Pandey, Green Chem. 2001, 3, 210-215.
79. J. F. Dye, T. A. Berger, Anal. Chem. 1990, 62, 615-622.
80. 2] is stable up to 400 °C, see ref.[3a]
81. - anion decomposes relatively easily in the presence of water: P. Wasserscheid, R. van Hal, A. Boesmann, Green Chem. 2002, 4, 400-404.
82. IR spectroscopy showed no vOH stretch frequencies.
83. 6 (R = methyl or butyl, x = 5 or 7) have been reported, but no solubility data were given, ref.[5d]
84. H. O. House, J. A. Hrabie, S. L. Narasimhan, J. Chem. Eng. Data 1986, 31, 124.
85. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser, R. D. Rogers, Chem. Commun. 1998, 1765-1766.
86. P. Lucas, N. E. Mehdi, H. A. Ho, D. Belanger, L. Breau, Synthesis 2000, 9, 1253-1258.
87. J. D. Wilkey, G. B. Schuster, J. Org. Chem. 1987, 52, 2117-2122.
88. J. T. Vandeberg, C. E. Moore, F. P. Cassaretto, H. Posvic, Anal. Chim. Acta 1969, 44, 175-183.
89. [471 M. Brookhart, B. Grant, A. F. Volpe, Organometallics 1992, 11, 3920-3922.
90. J. van den Broeke, E. de Wolf, B.-J. Deelman, G. van Koten, Adv. Synth. Catal. 2003, 345, 625-635.
91. G. M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, University of Göttingen, Germany, 1997.
92. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, A. Giacovazzo, A. Guagliardi, G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. 1999, 32, 115-119.
93. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
94. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, The Netherlands, 2002.