Imidazolium-based dicationic cyclophanes. Solid-state aggregates with unconventional (C-H)+ ⋯Cl- hydrogen bonding revealed by X-ray diffraction

Supramolecular Chemistry

Volumn 19, Issue 7, 2007, Pages 501-509

  Alcalde, Ermitas ^a   Mesquida, Neus ^a   Vilaseca, Marta ^a   Alvarez Rúa, Carmen ^b   García Granda, Santiago ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Anion recognition; Charged cyclophanes; Electrospray mass spectrometry; Hydrogen bonds; Templated synthesis; X ray diffraction crystallography

Indexed keywords

EID: 35549002860     PISSN: 10610278     EISSN: 10290478     Source Type: Journal    
DOI: 10.1080/10610270601132624     Document Type: Article

References (51)

1. Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. 2001, 40, 486.
2. Gale, P. A. Coord. Chem. Rev. 2001, 213, 79.
3. Gale, P. A. Coord. Chem. Rev. 2002, 240, 191.
4. Gale, P. A. Annu. Rep. Chem. Sect B 2004, 100, 207.
5. Gale, P. A. Annu. Rep. Chem., Sect B 2005, 202, 148.
6. Matthews, S. E.; Beer, P. D. Supramol. Chem. 2005, 17, 411.
7. Sessler, J. L.; Gale, P. A.; Cho, W. -S. Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, 2006.
8. Gale, P. A. Acc. Chem. Res. 2006, 39, 465.
9. Beer, P. D.; Sambrook, M. R.; Curiel, D. Chem. Commun. 2006, 2105.
10. Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006, 35, 355.
11. Vilar, R. Angew. Chem. Int. Ed. 2003, 2, 1460.
12. Steiner, T. Angew. Chem. Int. Ed. 2002, 41, 48.
13. Steiner, T. Acta Crystallogr. Section B54 1998, 456.
14. Nishio, M. CrystEngComm. 2004, 6, 130.
15. Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem. Int. Ed. 2001, 40, 2382.
16. Metrangolo, P.; Resnati, G. Chem. Eur. J. 2001, 7, 2511.
17. Bates, G. W.; Kostermans, M.; Dehaen, W.; Gale, P. A.; Light, M. E. CrystEngComm. 2006, 8, 444.
18. Custelcean, R.; Delmau, L. H.; Moyer, B. A.; Sessler, J. L.; Cho, W-S; Gross, D.; Bates, G. W.; Brooks, S. J.; Light, M. E.; Gale, P. A. Angew. Chem. Int. Ed. 2005, 44, 2537.
19. Sessler, J. L.; Gross, D. E.; Cho, W-S.; Lynch, V. M.; Schmidtchen, F. P.; Bates, G. W; Light, M. E.; Gale, P. A. J. Am. Chem. Soc. 2006, 128, 12281.
20. Alcalde, E.; Alvarez-Rúa, C.; García-Granda, S.; García-López, E.; Mesquida, N.; Pérez-García, L. Chem. Commun. 1999, 295.
21. Tomapatanaget, B.; Tuntulani, T.; Wisner, J. A.; Beer, P. Tetrahedron Lett. 2004, 45, 663.
22. Wong, W. W. H.; Vickers, M. S.; Cowley, A. R.; Paul, R. L.; Beer, P. D. Org. Biomol. Chem. 2005, 3, 4201.
23. Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R.; Szemes, F.; Drew, M. G. B. J. Am. Chem. Soc. 2005, 127, 2292.
24. Chellappan, C.; Singh, N. J.; Hwang, I. -C.; Lee, J. W.; Kim, K. S. Angew. Chem. Int. Ed. 2005, 44, 2899.
25. Fahlbusch, T.; Frank, M.; Schatz, J.; Schmaderer, H. Eur. J. Org. Chem. 2006, 1899.
26. Alcalde, E. Adv. Heterocycl. Chem. 1994, 60, 197.
27. Alcalde, E.; Mesquida, N.; Pérez-García, L.; Ramos, S.; Alemay, M.; Rodríguez, M. L. Chem. Eur. J. 2002, 8, 474.
28. Alcalde, E.; Mesquida, N.; Alemany, M.; Alvarez-Rúa, C.; García-Granda, S.; Pacheco, P.; Pérez-García, L. Eur. J. Org. Chem. 2002, 1221.
29. Alcalde, E.; Mesquida, N.; Pérez-García, L. Eur. J. Org. Chem. 2006, 3988.
30. Pérez-García, L.; Alcalde, E.; Mesquida, N.; Alemany, M.; Fernández, I.; Vilaseca, M. Eur. J. Org. Chem. 2002, 2691.
31. Alcalde, E.; Ramos, S.; Pérez-García, L. Org. Lett. 1999, 1, 1035.
32. Ramos, S.; Alcalde, E.; Doddi, G.; Mencarelli, P.; Pérez- García, L. J. Org. Chem. 2002, 67, 8463.
33. Alcalde, E.; Mesquida, N.; Vilaseca, M. Rapid Commun. Mass Spectrom. 2000, 24, 1443.
34. Konstantinchenko, A. A.; Morkovnik, A. S.; Pozharskii, A. F.; Tertov, B. A. Chem. Heterocycl. Compd. Engl. Transl. 1985, 1398.
35. Arduengo III, A. J.; Rasika Dias, H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
36. Thummel, R. P. J. Org. Chem. 1989, 54, 3057.
37. Shi, Z.; Thummel, R. P. J. Org. Chem. 1995, 60, 5935.
38. Díez-Barra, E.; Dotor, J.; Foces-Foces, C.; Enjabl, C.; Aubagnac, J. L.; Claramunt, R. M.; Elguero, J. Tetrahedron 1997, 53, 7689.
39. Cole, R. B. Electrospray Ionization Mass Spectrometry; John Wiley & Sons: New York, 1997.
40. Zhu, J. H.; Cole, C. B. J. Am. Soc. Mass Spectrom. 2000, 11, 932.
41. Zhu, J. H.; Cole, C. B. J. Am. Soc. Mass Spectrom. 2002, 22, 1193.
42. Cai, Y.; Cole, R. B. Anal. Chem. 2002, 74, 985.
43. Kumar, M. R.; Prabhakar, S.; Kimar, M. K.; Reddy, T. J.; Vairamani, M. Rapid Commun. Mass. Spectrom. 2004, 18, 1109.
44. Alcalde, E.; Mesquida, N.; Fernández, I.; Giralt, E. Rapid Commun. Mass. Spectrom. 2000, 14, 1014.
45. Neus Mesquida, Ph.D. Thesis, University of Barcelona, 1999, Barcelona (Spain).
46. CCDC deposition numbers 102466 and 102467.
47. The atom numbering system used for the X-ray data is not the same as that directly obtained from the single-crystal X-ray crystallographic analysis.
48. Gale, P. A.; Sessler, J. L.; Král, V. Chem. Commun. 1998, 1.
49. Baker, M. V.; Bosnisch, M. J.; Williams, C. C.; Skelton, B. W.; White, A. H. Aus. J. Chem. 1999, 52, 823.
50. Yuan, Y.; Zhou, H.; Jiang, Z.; Yang, J.; Xie, R. Acta Cryst (C) 2000, 56, 34.
51. Moore, S. S.; Tarnowski, T. L.; Newcomb, M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6398.