View PDF Version
 
DOI: 10.1039/A808503J (Paper) Reference Section for: Chem. Commun., 1999, 295-296

Hydrogen bonded driven anion binding by dicationic [14]imidazoliophanes

(Note: The full text of this document is currently only available in the PDF Version )

Ermitas Alcalde, Neus Mesquida, Lluïsa Pérez-García, Carmen Alvarez-Rúa, Santiago García-Granda and Esther García-Rodriguez

Abstract

Imidazolium units represent the main structural motifs for the formation of unconventional C–H···Cl– hydrogen bonds which become the noncovalent forces driving the anion interactions exibited by dicationic [14]imidazoliophanes in the solid state, while C–H···O hydrogen bonds with water play a crucial role in governing the conformation of the solid–state aggregates, as well as in solution, wherein NMR studies also reveal the importance of hydrogen bonds in controlling the tendency to anion binding.

References

  1. M. C. T. Fyfe and J. F. Stoddart, Acc. Chem. Res., 1997, 30, 393 CrossRef CAS.
  2. Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. García-España, Wiley-VCH, New York, 1997 Search PubMed; F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609 Search PubMed.
  3. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, Oxford, 1997 Search PubMed; The Crystal as a Supramolecular Entity, ed. G. R. Desiraju, Wiley, Chichester, 1996 Search PubMed.
  4. For some examples on C–H⋯anion hydrogen bonds, see: S. Shinoda, M. Tadokoro, H. Tsukube and R. Arakawa, Chem. Commun., 1998, 181 Search PubMed; B. Koning, R. Hulst, A. Bouter, J. Buter, A. Meetsma and R. M. Kellogg, Chem. Commun., 1997, 1065 RSC; M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White and D. J. Williams, Angew. Chem., Int. Ed. Engl., 1997, 36, 2068 RSC; R. E. Cramer, V. Fermin, E. Kuwabara, R. Kirkup, M. Selma, K. Aoki, A. Adeyemo and H. Yamakazi, J. Am. Chem. Soc., 1991, 113, 7033 CrossRef CAS.
  5. E. Alcalde, M. Alemany, L. Pérez-García and M. L. Rodríguez, J. Chem. Soc., Chem. Commun., 1995, 1239 RSC and references cited therein E. Alcalde, M. Alemany and M. Gisbert, Tetrahedron, 1996, 52, 15171 Search PubMed.
  6. P. K. Dahl and F. H. Arnold, J. Am. Chem. Soc., 1991, 113, 7417 CrossRef CAS.
  7. S. S. Moore, T. L. Tarnowski, M. Newcomb and D. J. Cram, J. Am. Chem. Soc., 1977, 99, 6398 CrossRef CAS.
  8. E. Alcalde, I. Dinarés, J. Frigola, C. Jaime, J.-P. Fayet, M.-C. Vertut, C. Miravitlles and J. Rius, J. Org. Chem., 1991, 56, 4223 CrossRef CAS.
  9. M. G. Shieldrick, Acta. Crystallogr., 1990, A46, 467 CrossRef CAS.
  10. G. M. Sheldrick, Crystallographic Computing, ed. G. H. D. Flack, P. Parkanyi and K. Simon, Oxford University Press, Oxford, 1993, p. 111 Search PubMed.
  11. T. Kottke and D. Stalke, J. Appl. Crystallogr., 1993, 26, 615 CrossRef.
  12. T. Steiner, Acta. Crystallogr., 1998, B54, 456 CAS and references cited therein.
  13. P. A. Gale, J. L. Sessler and V. Král, Chem. Commun., 1998, 1 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.