Skip to main content
Log in

NMR and potentiometric determination of the high pK values and protonation sequence of dipyridino-hexaaza-28-crown-8 and its interactions with selenate, sulfate and nitrate ions in aqueous solution

  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

The aqueous protonation and anion-binding SeO −/42 SO 42− , and NO 3 ) constants of the macrocyclic polyamine ligand, dipyridino-hexaaza-28-crown-8(L), were measured in 0.1M KCl using a potentiometric titration technique. The protonation sequence of the aza groups of L was studied in D2O from the chemical shifts of the nonlabile protons so as to find the charge distribution geometry as a function of pD. The study indicates that in 0.1M KC1 fully protonated L forms stable l: 1 complexes with SeO 42− (logK=3.68) and SO 42− (logK=3.55), but not with NO 3 (logK < l.5). All of the amine pK values were above 6.3, thus allowing the use of the protonated form of this ligand over a wide pH range.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. W. Hosseini, J. M. Lehn and M. P. Mertes:Helv. Chim. Acta 66, 2454 (1983).

    Google Scholar 

  2. E. Kimura, T. Koike and M. Kodama:Chem. Pharm. Bull. Jpn. 32, 3569 (1984).

    Google Scholar 

  3. E. Kimura: ‘Macrocyclic Polyamines as Biological Cation and Anion Complexones — An Application to Calculi Dissolution', inTop. Curr. Chem. 128, 113 (1985).

    Google Scholar 

  4. National Research CouncilDrinking Water and Health, National Academy of Sciences, Washington, D.C., 1977.

    Google Scholar 

  5. S. E. Carson and K. K. Hank:Ultrapure Water 4, 47 (1987).

    Google Scholar 

  6. F. W. Pontius:J. Am. Water Works Assoc. 82, 32 (1990).

    Google Scholar 

  7. C. J. King, Chairman,Separation and Purification: Critical Needs and Opportunities, Report to the National Research Council by the Committee on Separation Science and Technology, National Academy Press, Washington, D.C., 1987.

    Google Scholar 

  8. R. M. Izatt, K. Pawlak, R. L. Bruening, J. S. Bradshaw:Chem. Rev. 91, 1721 (1991).

    Google Scholar 

  9. A. Bencini, A. Bianchi, E. G. Espana, M. Giusti, S. Mangan, M. Micheloni, P. Orioli and P. Paoletti:Inorg. Chem. 26, 3902 (1987).

    Google Scholar 

  10. C. H. Park and H. E. Simmons:J. Am. Chem. Soc. 90, 2431 (1968).

    Google Scholar 

  11. E. Graf and J.-M. Lehn:J. Am. Chem. Soc. 98, 6403 (1976).

    Google Scholar 

  12. B. Dietrich, M. W. Hosseini, J.-M. Lehn and R. B. Sessions:J. Am. Chem. Soc. 103, 1282 (1981).

    Google Scholar 

  13. F. P. Schmidtchen:Top. Curr. Chem. 132, 101 (1986).

    Google Scholar 

  14. A. Bianchi, M. Micheloni and P. Paoletti:Inorg. Chim. Acta 151, 269 (1988).

    Google Scholar 

  15. M. W. Hosseini and J.-M. Lehn:Helv. Chim. Acta 70, 1312 (1987).

    Google Scholar 

  16. M. W. Hosseini and J.-M. Lehn:Helv. Chim. Acta 71, 749 (1988).

    Google Scholar 

  17. E. Kimura, A. Sakonaka, T. Yatsunami and M. Kodama:J. Am. Chem. Soc. 103, 3041 (1981).

    Google Scholar 

  18. M. W. Hosseini, J. Comarmond and J.-M. Lehn:Helv. Chim. Acta 72, 1066 (1989).

    Google Scholar 

  19. F. P. Schmidtchen, A. Gleich and A. Schummer:Pure Appl. Chem. 61, 1535 (1989).

    Google Scholar 

  20. K. E. Krakowiak, J. S. Bradshaw, W. Jiang, N. K. Dalley, G. Wu and R. M. Izatt:J. Org. Chem. 56, 2675 (1991).

    Google Scholar 

  21. P. Gans, A. Sabatini, and A. Vacca:J. Chem. Soc. Dalton Trans. 1195 (1985).

  22. R. Maggiore, S. Musumeci and S. Sammartano:Talanta 23, 43 (1976).

    Google Scholar 

  23. K. Mikkelsen and S. O. Nielson:J. Phys. Chem. 64, 632 (1960).

    Google Scholar 

  24. E. Martell and R. M. Smith: Critical Stability Constants, Plenum Press, New York, NY, 1982.

    Google Scholar 

  25. J. L. Sudmeier and C. N. Reilley:Anal. Chem. 36, 1699 (1964).

    Google Scholar 

  26. J. Cullinane, R. I. Gelb, T. N. Margulis and L. J. Zompa:J. Am. Chem. Soc. 104, 3048 (1982).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wu, G., Izatt, R.M., Bruening, M.L. et al. NMR and potentiometric determination of the high pK values and protonation sequence of dipyridino-hexaaza-28-crown-8 and its interactions with selenate, sulfate and nitrate ions in aqueous solution. J Incl Phenom Macrocycl Chem 13, 121–127 (1992). https://doi.org/10.1007/BF01053635

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01053635

Key words

Navigation