View PDF Version
 
DOI: 10.1039/A702389H (Paper) Reference Section for: Chem. Commun., 1997, 1685-1686

(cis)-5,10,15,20-Tetrakis[2-(arylurea)phenyl]porphyrins: novel neutral ligands for remarkably selective and exceptionally strong chloride anion complexation in (CD3)2SO

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

Raymond C. Jagessar and Dennis H. Burns

Abstract

Urea appended free-base porphyrins 2–4 bind strongly (K > 105 dm3 mol-1) to spherical Cl- in (CD3)2SO and exhibit significant binding selectivity since they complex with Cl- to a much greater extent (103–102:1) than with the trigonal NO3- and tetrahedral H2PO4- anions.

References

  1. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529 CrossRef CAS; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457 CrossRef CASFor more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H.. Crabtree, J. Am. Chem. Soc., 1997, 119, 2325 CrossRef CAS; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793 CrossRef CAS; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947 CrossRef CAS; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595 CrossRef CAS; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140 CrossRef CAS.
  2. J. Scheerder, J. F. J. Engbersen, A. Casnati, R. Ungaro and D. N. Reinhoudt, J. Org. Chem., 1995, 60, 6448 CrossRef CAS.
  3. P. Bühlmann, S. Nishizawa, K. P. Xiao and Y. Umezawa, Tetrahedron, 1997, 53, 1647 CrossRef CAS.
  4. J. Scheerder, M. Fochi, J. F. J. Engbersen and D. N. Reinhoudt, J. Org. Chem., 1994, 59, 7815 CrossRef CAS.
  5. E. Fan, S. A. Van Arman, S. Kincaid and A. D. Hamilton, J. Am. Chem. Soc., 1993, 115, 369 CrossRef CAS.
  6. B. C. Hamann, N. R. Branda and J. Rebek, Tetrahedron Lett., 1993, 34, 6837 CrossRef CAS.
  7. L. Stryer, Biochemistry, W. H. Freeman, New York, 1988, pp. 963–964 Search PubMed; J. W. Hanrahan, J. A. Tabcharani, F. Becq, C. J. Mathews, O. Augustinas, T. J. Jensen, X.-B. Chang and J. R. Riordan, in Ion Channels and Genetic Diseases, ed. D. C. Dawson and R. A. Frizzel, Rockefeller University Press, New York, 1995 Search PubMed.
  8. P. D. Beer, M. G. B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc., Chem. Commun., 1995, 1187 RSC; P. D. Beer, Chem. Commun., 1996, 689 RSC; P. D. Beer, M. G. B. Drew and R. Jagessar, J. Chem. Soc., Dalton Trans., 1997, 881 RSC.
  9. T. N. Sorrell, Inorg. Synth., 1980, 20, 163.
  10. J. S. Lindsey, J. Org. Chem., 1980, 45, 5215 CrossRef CAS.
  11. A. D. Adler, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour and L. Korsakoff, J. Org. Chem., 1967, 32, 476 CrossRef CAS.
  12. The computer program EQNMR was used to calculate binding constants: M. J. Hynes, J. Chem. Soc., Dalton Trans., 1993, 311 Search PubMed.
  13. Binding constants greater than 105 dm3 mol–1 cannot be determined accurately: T. Wang, J. S. Bradshaw and R. M. Izatt, J. Heterocycl. Chem., 1994, 31, 1097 Search PubMed.
  14. K. A. Connors, Binding Constants, Wiley, New York, 1987, pp. 24–28 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.