Dibenzylimidazolium halides: From complex molecular network in solid state to simple dimer in solution and in gas phase

Journal of Physical Chemistry A

Volumn 112, Issue 22, 2008, Pages 4996-5001

  Leclercq, Loïc ^a   Schmitzer, Andreea R ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; FLOW INTERACTIONS; GAS DYNAMICS; HYDROGEN; HYDROGEN BONDS; NETWORK PROTOCOLS; SENSOR NETWORKS; SOLID SOLUTIONS;

AROMATIC STACKING INTERACTIONS; COMPLEX MOLECULAR NETWORK; GAS-PHASE; SOLID STATES; STRUCTURAL ORGANIZATIONS;

GASES;

EID: 52349120650     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp801172m     Document Type: Article

References (67)

1. Handy, S. T. Chem. Eur. J. 2003, 9, 2938-2944.
2. (a) Holbrey, J. D.; Seddon, K. R. Clean Products Processes 1999, 1, 223-236.
3. (b) Hagiwara, R.; Ito, Y. J. Fluorine Chem. 2000, 105, 221-227.
4. (c) Scammells, P. J.; Scott, J. L.; Singer, R. D. Aust. J. Chem. 2005, 58, 155-169.
5. (a) Zhao, H.; Malhotra, S. V. Aldrich. Acta 2002, 35, 75-83.
6. (b) Chauvin, Y.; Olivier-Bourbigou, H. CHEMTECH 1995, 25, 26-30.
7. (c) Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351-356.
8. (d) Sheldon, K. R. Chem. Commun. 2001, 2399-2407.
9. (e) Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A. C.; Plaquevent, J. C. Tetrahedron: Asymm. 2003, 14, 3081-3093.
10. (f) Mehnert, C. P. Chem. Eur. J. 2005, 11, 50-56.
11. (g) Blaser, H.-U.; Studer, M. Green Chem. 2003, 5, 112-117.
12. (h) Song, C. E. Chem. Commun. 2004, 1033-1043.
13. (j) Park, S.; Kazlauskas, R. J. Curr. Opin. Biotechnol. 2003, 14, 432-437.
14. (j) Kragl, U.; Eckstein, M.; Kaftzik, N. Curr. Opin. Biotechnol. 2002, 13, 565-571.
15. (k) Poole, C. F. J. Chromatogr. A 2004, 1037, 49-82.
16. (l) Stalcup, A. M.; Cabovska, B. J. Liq. Chromatogr. Relat. Technol. 2004, 27, 1443-1459.
17. (m) Antonietti, M.; Kuang, D. B.; Smarsly, B.; Yong, Z. Angew. Chem., Int. Ed. 2004, 43, 4988-4992.
18. (n) Geetha, S.; Trivedi, D. C. Bull. Electrochem. 2003, 19, 37-48.
19. Chiappe, C.; Pieraccini, D. J. Phys. Org. Chem. 2005, 18, 275-297.
20. (a) Dupont, J. J. Braz. Chem. Soc. 2004, 15, 341-350.
21. (b) Avent, A. G.; Chaloner, P. A.; Day, M. P.; Seddon, K. R.; Weiten, T. J. Chem. Soc., Dalton Trans. 1994, 3405-3413.
22. Zhang, H.; Liang, H.; Wang, J.; Li, K. Z. Phys. Chem. 2007, 221, 1061-1074.
23. (a) Bowers, J.; Butts, C. P.; Martin, P. J.; Vergara-Gutierrez, M. C.; Heenan, R. K. Langmuir 2004, 20, 2191-2198.
24. (b) Dorbritz, S.; Ruth, W.; Kragl, U. Adv. Synth. Catal. 2005, 347, 1273-1279.
25. (c) Malham, I. B.; Letellier, P.; Turmine, M. J. Phys. Chem. B 2007, 110, 14212-14222.
26. (d) Katayanagi, H.; Nishikawa, K.; Shimozaki, H.; Miki, K.; Westh, P.; Koga, Y. J. Phys. Chem. B 2004, 108, 19451-19457.
27. (e) Consorti, C. S.; Suarez, P. A. Z.; de Souza, R. F. S.; Burrow, R. A.; Farrar, D. H.; Lough, A. J.; Loh, W.; da Silva, L. H. M.; Dupont, J. J. Phys. Chem. B 2005, 109, 4341-4349.
28. (a) Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley-VCH: Weinheim, 2000.
29. (b) Steed, J. W.; Atwood, J. L.; Supramolecular Chemistry; Wiley: Chichester, U.K., 2000.
30. (c) Philip, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
31. (d) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995.
32. Mann, S. Nature 1993, 365, 499-505.
33. Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991-6000.
34. (a) Gordon, C. M.; Holbrey, J. D.; Kennedy, A. R.; Seddon, K. R. J. Mater. Chem. 1998, 8, 2627-2636.
35. (b) Dupont, J.; Suarez, P. A. Z.; de Souza, R. F.; Burrow, R. A.; Kintzinger, J. P. Chem. Eur. J. 2000, 6, 2377-2381.
36. (c) van den Broeke, J.; Stam, M.; Lutz, M.; Kooijman, H.; Spek, A. L.; Deelman, B.-J.; van Koten, G. Eur. J. Inorg. Chem. 2003, 2798-2811.
37. (d) Holbrey, J. D.; Reichert, W. M.; Nieuwenhuyen, J. S.; Seddon, K. R.; Rogers, R. D. Chem. Commun. 2003, 1636-1837.
38. (e) Saha, S.; Hayashi, S.; Hamaguchi, H. Chem. Lett. 2003, 32, 740-741.
39. (f) Downard, A.; Earle, M. J.; Hardacre, C.; McMath, S. E. J.; Nieuwenhuyzen, M.; Teat, S. J. Chem. Mater. 2004, 16, 43-46.
40. (g) Holbrey, J. D.; Reichert, W. M.; Rogers, R. D. Dalton Trans. 2004, 15, 2267-2271.
41. (h) Golovanov, D. G.; Lyssenko, K. A.; Antipin, M. Y.; Vygoskii, Y. S.; Lozinskaya, E. I.; Shaplov, A. S. Cryst. Eng. Comm 2005, 6, 53-56.
42. (i) Fujimoto, T.; Kawahata, M.; Nakakoshi, Y.; Yamaguchi, K.; Machinami, T.; Nischikawa, K.; Tashiro, M. Anal. Sci. 2007, 23, 107-108.
43. (j) Nakakoshi, Y.; Shiro, M.; Fujimoto, T.; Machinami, T.; Seki, H.; Tashiro, M.; Nischikawa, K. Chem. Lett. 2006, 35, 1400-1401.
44. (k) Getsis, A.; Mudring, A.-V. Acta Crystallogr. 2005, E61, 2945-2946.
45. Dupont, J.; Suarez, P. A. Z. Phys. Chem. Phys. Chem. 2006, 8, 2441-2452.
46. (a) Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366-4374.
47. (b) Alder, R. W.; Allen, P. R.; Williams, S. J. J. Chem. Soc., Chem. Commun. 1995, 1267-1268.
48. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, U.K., 1997.
49. (a) For π-stacking in supramolecular aggregates see: Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319.
50. (b) Sirish, M.; Schneider, H. J. J. Am. Chem. Soc. 2000, 122, 5881-5882.
51. (c) Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222.
52. Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2003; Chapter 2.
53. Leclercq, L.; Suisse, I.; Nowogrocki, C.; Agbossou Niedercorn, F. Green Chem. 2007, 9, 1097-1103.
54. (a) Schmuck, G Chem. Eur. J. 2000, 6, 709-718.
55. (b) Dixon, R. D.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 365-366.
56. (a) Wilcox, C. S. In Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H. J., Dürr, H. Eds.; VCH: Weinheim, 1990.
57. (b) Connors, K. A. Binding Constants; Wiley: New York, 1987.
58. (a) Bangerter, B. W.; Chan, S. I. J. Am. Chem. Soc. 1969, 91, 3910-3919.
59. (b) Davis, J. C., Jr.; Deb, K. K. Adv. Magn. Reson. 1970, 4, 201-270.
60. (a) Gozzo, F. C.; Santos, L. S.; Augusti, R.; Consorti, C. S.; Dupont, J.; Eberlin, M. N. Chem. Eur. J. 2004, 10, 6187-6193.
61. (b) Bini, R.; Bortolini, O.; Chiappe, C.; Pieraccini, D.; Siciliano, T. J. Phys. Chem. B 2007, 111, 598-604.
62. (a) Koch, K. J.; Gozzo, F. C.; Nanita, S. C.; Takats, Z.; Eberlin, M. N.; Cooks, R. G. Angew. Chem., Int. Ed. 2002, 41, 1721-1724.
63. (b) Takats, Z.; Nanita, S. C.; Cooks, R. G. Angew. Chem., Int. Ed. 2003, 42, 3521-3523.
64. (c) Cooks, R. G.; Zhang, D. X.; Koch, K. J.; Gozzo, F. C.; Eberlin, M. N. Anal. Chem. 2001, 73, 3646-3655.
65. (a) Wang, G.; Cole, R. D. Anal. Chem. 1998, 70, 873-881.
66. (b) Hao, C.; March, R. E. J. Mass Spectrom. 2001, 36, 509-521.
67. Smith, M. B.; March, J. Mechanisms and Methods of Determining Them in March's Advanced Organic Chemistry, 6th ed.; John Wiley & Sons: New York, 2007.