Intramolecular C–HO hydrogen bonding reduces cation complexation strength in a fluorescent crown ether

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

Stephen L. De Wall, Eric S. Meadows, Leonard J. Barbour and George W. Gokel


Abstract

Complexes of the fluorescent crown ether, N,N-bis(9-anthrylmethyl)-4,13-diaza-18-crown-6, with NaI3 and KSCN reveal the presence of intramolecular C–H‥O hydrogen bonds that appear to control conformation and lead to reduced cation binding affinity.


References

  1. H.-G. Löhr and F. Vögtle, Acc. Chem. Res., 1985, 18, 65 CrossRef.
  2. G. W. Gokel and J. E. Trafton, Cation Binding by Lariat Ethers, in Cation Binding by Macrocycles, ed. Y. Inoue and G. Gokel, Marcel Dekker, New York, 1990, pp. 253–310; Search PubMed; G. W. Gokel, Chem. Soc. Rev., 1992, 21, 39 Search PubMed; G. W. Gokel and O. F. Schall, Lariat Ethers, in Comprehensive Supramolecular Chemistry, ed. G. Gokel, Pergamon, Oxford, 1996, vol. 1, pp. 97–152 RSC.
  3. Fluorescent Chemosensors for Ion and Molecule Recognition, ed. A. W. Czarnik, ACS Symp. Ser.ACS, Washington, DC, 1993, vol. 538 Search PubMed.
  4. A. P. de Silva and S. A. de Silva, J. Chem. Soc., Chem. Commun., 1986, 1709 RSC.
  5. U. Herrmann, B. Tümmler, G. Maas, P. K. T. Mew and F. Vögtle, Biochemistry, 1984, 23, 4059 CrossRef CAS; B. Tümmler, U. Herrmann, G. Maas and H. Eibl, Biochemistry, 1984, 23, 4068 CrossRef CAS.
  6. R. A. Bissell, E. Calle, A. P. deSilva, S. A. deSilva, H. Q. N. Gunaratne, J.-L. Habib-Jiwan, S. L. A. Peiris, R. A. D. D. Rupasinghe, T. K. S. D. Samarasinge, K. R. A. S. Sandanayake and J.-P. Soumillon, J. Chem. Soc., Perkin Trans. 2, 1992, 1559 RSC.
  7. D. Marquis, J.-P. Desvergne and H. Bouas-Laurent, J. Org. Chem., 1995, 60, 7984 CrossRef CAS.
  8. J. H. R. Tucker, H. Bouas-Laurent, P. Marsau, S. W. Riley and J.-P. Desvergne, Chem. Commun., 1997, 1165 RSC.
  9. G. DeSantis, L. Fabbrizzi, M. Licchelli, C. Mangano, D. Sacchi and N. Sardone, Inorg. Chim. Acta, 1997, 257, 69 CrossRef CAS.
  10. C. R. Cooper and T. D. James, Chem. Commun., 1997, 1419 RSC.
  11. V. J. Gatto, S. R. Miller and G. W. Gokel, Org. Synth., 1989, 68, 227.
  12. Combustion analysis: Calc. for C42H46N2O4: C, 78.47; H, 7.21; N, 4.36%. Found: C, 78.44; H, 7.34; N, 4.28%.
  13. R. D. Gandour, F. R. Fronczek, V. J. Gatto, C. Minganti, R. A. Schultz, B. D. White, K. A. Arnold, D. Mazzocchi, S. R. Miller and G. W. Gokel, J. Am. Chem. Soc., 1986, 108, 4078 CrossRef CAS.
  14. K. Kubo, R. Ishige and T. Sakuri, Heterocycles, 1998, 48, 347 CrossRef CAS.
  15. D. M. Dishong and G. W. Gokel, J. Org. Chem., 1982, 47, 147 CrossRef CAS.
  16. R. D. Shannon, Acta Crystallogr., Sect. A, 1976, 32, 751 CrossRef.
  17. G. R. Desiraju, Acc. Chem. Res., 1996, 29, 441 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.