Skip to main content
SpringerLink
Log in

Synthesis of Tetra-N-substituted 1,10-dioxa-4,7,13,16- tetraazacyclooctadecanes and their Application as Lead (II) Selective Electrodes. X-ray Crystal Structure of 4,7,13,16-tetrathenoyl-1,10- dioxa-4,7,13,16-tetraazacyclooctadecane

  • Published:
Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

Tetra-N-substituted 1,10-dioxa-4,7,13,16-tetraazacyclooctadecanes (tetraazacrown ethers) (1-5) have been synthesised. Each compound was incorporated in a PVC membrane that provided the basis for a lead-selective potentiometric electrode. The electrode based on the 4,7,13,16-tetrathenoyl-1,10-dioxa-4,7,13,16- tetraazacyclooctadecane (5) ionophore bearing four thenoyl functional subunits exhibited excellent lead (II) ion selectivity with only Ag+ and Hg2+ significantly interfering. The crystal structure of this host (5) has been determined by single crystal X-ray analysis. Crystal data. C32H36N4O6S4, M 700.9, monoclinic, space group P21/c, a, 10.315(4), b, 13.635(2), c, 14.357(6)Å, β 124.63(2)°, V 1661.6(9)Å3, Dc 1.40 g cm-3, Z 2, μ Cu 29.90 cm-1. Final residuals R, Rw were 0.054, 0.082 for the observed data.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Z. Brozozka, M. Pietraszkiewicz, and R. Gasiorowski: J. Incl. Phenom. 9, 259 (1990).

    Google Scholar 

  2. Z. Brozozka and M. Pietraszkiewicz: Electroanalysis 3, 855 (1991).

    Google Scholar 

  3. M. Pietraszkiewicz and R. Gasiorowski: J. Incl. Phenom. 14, 237 (1992).

    Google Scholar 

  4. E. Malinowska, J. Jurczak, and T. Stankiewicz: Electroanalysis 5, 489 (1993).

    Google Scholar 

  5. K. Suzuki, K. Watanabe, Y. Matsumoto, M. Kobayashi, S. Sato, D. Siswanta, and H. Hisamoto: Anal. Chem. 67, 324 (1995).

    Google Scholar 

  6. H. Tsukube, K. Takagi, T. Higashiyama, T. Iwachido, and N. Hayama: J. Chem. Soc. Perkin Trans. 1. 1033 (1996).

  7. X. Yang, N. Kumar, H. Chi, D. B. Hibbert, and P.W. Alexander: Electroanalysis 9, 549 (1997).

    Google Scholar 

  8. K. E. Krakowiak, J. S. Bradshaw, and D. J. Zamecka-Krakowiak: Chem. Rev. 89, 929 (1989).

    Google Scholar 

  9. N. G. Luk'yanenko, S. S. Basok, and L. K. Filonova: Zh. Org. Khim. 24, 1562 (1988).

    Google Scholar 

  10. J. F. Biernat and E. Luboch: Tetrahedron 40, 1927 (1984).

    Google Scholar 

  11. P.W. Wade, R. D. Hancock, J. C. A. Boeyens, and S. M. Dobson: J. Chem. Soc., Dalton Trans. 483 (1990).

  12. J. De Meulenaer and H. Tompa: Acta Crystallogr. 19, 1014 (1965).

    Google Scholar 

  13. J. A. Ibers and W. C. Hamilton (Eds.): International Tables for X-Ray Crystallography, Vol. 4, Kynoch Press, Birmingham, (1974).

    Google Scholar 

  14. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, and G. Polidori: J. Appl. Crystallogr. 27, 435 (1994).

    Google Scholar 

  15. W. R. Busing, K. O. Martin, and H. A. Levy: ORFLS, Oak Ridge National Laboratory, Tennessee, U.S.A., (1962).

    Google Scholar 

  16. C. K. Johnson: ORTEP-II, Oak Ridge National Laboratory, Tennessee, U.S.A., (1976).

    Google Scholar 

  17. H. A. Laitinen and W. E. Harris: Chemical Analysis, McGraw-Hill, pp. 9–14, (1975).

  18. IUPAC: Recommendation for Nomenclature of Ion-Selective Electrodes, Pure Appl. Chem. 48, 129 (1976).

  19. H. Tsukube, K. Takagi, T. Higashixama, T. Iwachido, and N. Hayama: J. Incl. Phenom. 2, 103 (1984).

    Google Scholar 

  20. D. Tétard, A. Rabion, J-B. Verlhac, and J. Guilhem: J. Chem. Soc., Chem. Commun. 531 (1995).

Download references

Author information

Authors and Affiliations

  1. School of Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia

    Xinhao Yang, Donald C. Craig, Aresh Kumar & D. Brynn Hibbert

Authors
  1. Xinhao Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Donald C. Craig
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aresh Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. Brynn Hibbert
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, X., Craig, D.C., Kumar, A. et al. Synthesis of Tetra-N-substituted 1,10-dioxa-4,7,13,16- tetraazacyclooctadecanes and their Application as Lead (II) Selective Electrodes. X-ray Crystal Structure of 4,7,13,16-tetrathenoyl-1,10- dioxa-4,7,13,16-tetraazacyclooctadecane. Journal of Inclusion Phenomena 33, 135–148 (1999). https://doi.org/10.1023/A:1008080423071

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1008080423071

Search

Navigation