Skip to main content
Log in

A competitive polarographic study of complexation of ammonium, anilinium, hydrazinium and pyridinium ions with some macrocyclic ligands in binary ethanol-water mixtures using a Pb(II)/Pb(Hg) couple as an electrochemical probe

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

Abstract

The formation of ammonium, anilinium, hydrazinium and pyridinium ion complexes with the crown ethers 18-crown-6 (18C6) and 1,10-diaza-18-crown-6 (C22) and the cryptand C222 in different binary ethanol-water mixtures has been studied by a competitive polarographic method using a Pb2+/Pb(Hg) couple as a sensitive electro-chemical probe. Lead ion was found to form very stable complexes with the ligands used, in all solvent mixtures studied; Pb2+−C222 cryptate revealed a pronounced ‘cryptate effect’ compared to the corresponding complexes with the monocyclic crown ethers used. In all solvent mixtures studied, the stability of the resulting 1∶1 complexes between the protonated amines and macrocyclic ligands used vary in the order C22>C222>18C6. The observed selectivity order of each macrocyclic ligand used for different protonated amines is discussed based on the chemical and structural features of the host-guest partners in solution. In all cases studied there is an inverse linear relationship between the complex formation constants and the mole fraction of water in the mixed solvent.

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. C.J. Pedersen:J. Am. Chem. Soc. 89, 7017 (1967).

    Google Scholar 

  2. B. Dietrich, J.M. Lehn, and J.P. Sauvage:Tetrahedron Lett. 2885 (1969).

  3. C.J. Pedersen:Fed. Proc. Fed. Am. Soc. Exp. Biol. 27, 1305 (1968).

    Google Scholar 

  4. Yu.A. Ovchinnikov, V.T. Ivanov, and A.M. Shkrob:Membrane-Active Complexones, Elsevier, Amsterdam (1974).

    Google Scholar 

  5. D.J. Cram: inApplications of Biochemical Systems in Organic Chemistry, Part (Ed. J. B. Jones) Wiley, New York (1976).

    Google Scholar 

  6. K.A. Rubinson:J. Chem. Educ. 54, 345 (1977).

    Google Scholar 

  7. R.M. Izatt, N.E. Izatt, B.E. Rossiter, and J.J. Christensen:Science 199, 994 (1978).

    Google Scholar 

  8. R.M. Izatt, J.D. Lamb, N.E. Izatt, B.E. Rossiter, J.J. Christensen, and B.L. Haymore:J. Am. Chem. Soc. 101, 6273 (1979).

    Google Scholar 

  9. J.M. Lehn and P. Vierling:Tetrahedron Lett 1323 (1980).

  10. E. Graf, J.P. Kintzinger, J.M. Lehn, and J. LeMoigne:J. Am. Chem. Soc. 104, 1672 (1982).

    Google Scholar 

  11. R.A. Schultz, E. Schlegel, D.M. Dishong, and G.W. Gokel:J. Chem. Soc., Chem. Commun. 242 (1982).

  12. J.P. Behr, J.M. Lehn, and P. Vierling:Helv. Chim. Acta 65, 1853 (1982).

    Google Scholar 

  13. R.A. Schultz, B.D. White, D.M. Dishong, K.A. Arnold, and G.W. Gokel:J. Am. Chem. Soc. 107, 6659 (1985).

    Google Scholar 

  14. S. Petrucci, R.J. Adamic, and E.M. Eyring:J. Phys. Chem. 90, 1677 (1986).

    Google Scholar 

  15. J.S. Bradshaw, P. Huszthy, C.W. McDaniel, C.Y. Zhu, N.K. Dalley, and R.M. Izatt:J. Org. Chem. 55, 129 (1990).

    Google Scholar 

  16. C.Y. Zhu, R.M. Izatt, J.S. Bradshaw, and N.K. Dalley:J. Incl. Phenom. 13, 17 (1992).

    Google Scholar 

  17. M. Hasani and M. Shamsipur:J. Incl. Phenom. 16, 123 (1993).

    Google Scholar 

  18. M. Hasani and M. Shamsipur:J. Solution Chem. 23, 721 (1994).

    Google Scholar 

  19. A. Semnani and M. Shamsipur:J. Electroanal. Chem. 315, 95 (1991).

    Google Scholar 

  20. H. Parham and M. Shamsipur:J. Electroanal. Chem. 314, 71 (1991).

    Google Scholar 

  21. S. Kashanan and M. Shamsipur:Inorg. Chim. Acta 155, 203 (1989).

    Google Scholar 

  22. H. Parham and M. Shamsipur:Polyhedron 11, 987 (1992).

    Google Scholar 

  23. D.R. Crow:Polarography of Metal Complexes, Academic Press, New York (1969).

    Google Scholar 

  24. I.M. Kolthoff and J.J. Lingane:Polarography, 2nd ed., Interscience, New York (1952).

    Google Scholar 

  25. M. Kodama and E. Kimura:Inorg. Chem. 17, 2446 (1978);Bull. Chem. Soc. Jpn. 49, 2465 (1976).

    Google Scholar 

  26. C. Luca, H.A. Azab, and I. Tanase:Anal. Lett. 18, 449 (1985).

    Google Scholar 

  27. L. Chen, M. Bos, P.D.J. Grootenhuis, A. Christenhusz, E. Hoogendam, D.N. Reinhoudt, and W.E. Van der Linden:Anal. Chim. Acta 201, 117 (1987).

    Google Scholar 

  28. V. Gutmann and E. Wychera:Inorg. Nucl. Chem. Lett. 2, 257 (1966).

    Google Scholar 

  29. M. Shamsipur and A.I. Popov:J. Am. Chem. Soc. 101, 4051 (1979).

    Google Scholar 

  30. M. Shamsipur, S. Madaeni, and S. Kashanian:Talanta 36, 773 (1989).

    Google Scholar 

  31. M.K. Amini and M. Shamsipur:Inorg. Chim. Acta 183, 65 (1991).

    Google Scholar 

  32. J. Ghasemi and M. Shamsipur:J. Coord. Chem. 23, 337 (1992).

    Google Scholar 

  33. M. Shamsipur and A.I. Popov:J. Phys. Chem. 91, 447 (1987).

    Google Scholar 

  34. M. Shamsipur and A.I. Popov:J. Phys. Chem. 92, 147 (1988).

    Google Scholar 

  35. M.K. Amini and M. Shamsipur:J. Phys. Chem. 95, 9601 (1991).

    Google Scholar 

  36. R.H. Erlish and A.I. Popov:J. Am. Chem. Soc. 93, 5620 (1971).

    Google Scholar 

  37. A. Rouhollahi, M.K. Amini, and M. Shamsipur:J. Solution Chem 23, 63 (1994).

    Google Scholar 

  38. M. Shamsipur and A. Semnani:Iran. J. Sci. Technol. 18, 23 (1994).

    Google Scholar 

  39. M. Shamsipur and J. Ghasemi:J. Incl. Phenom. 20, 157 (1995).

    Google Scholar 

  40. J. Ghasemi and M. Shampsipur:J. Solution Chem. In press.

  41. H. Khajesharifi and M. Shamsipur:J. Coord. Chem. 35, 289 (1995).

    Google Scholar 

  42. M. Shamsipur, A. Esmaeili, and M.K. Amini:Talanta 36, 1300 (1989).

    Google Scholar 

  43. M. Saeidi and M. Shamsipur:J. Coord. Chem. 22, 131 (1990).

    Google Scholar 

  44. M.R. Fat'hi and M. Shamsipur:Spectrosc. Lett. 26, 1797 (1993).

    Google Scholar 

  45. J.M. Lehn:Struct. Bonding (Berlin) 16, 1 (1973).

    Google Scholar 

  46. R.D. Shannon:Acta Crystallogr., Sect. A 32, 751 (1976).

    Google Scholar 

  47. M. Kodama and E. Kimura:J. Chem. Soc. Dalton Trans. 2269 (1977);ibid. 1081 (1978).

  48. J.M. Lehn and J.P. Sauvage:J. Am. Chem. Soc. 97, 6700 (1975).

    Google Scholar 

  49. A. Pullman and A.M. Armbruster:Chem. Phys. Lett. 36, 558 (1975).

    Google Scholar 

  50. P. Kollmann:J. Am. Chem. Soc. 99, 4875 (1977).

    Google Scholar 

  51. J.F. Griffin and P. Coppens:J. Am. Chem. Soc. 97, 3496 (1975).

    Google Scholar 

  52. D.J. Cram and J.M. Cram:Science 183, 803 (1974).

    Google Scholar 

  53. S.N. Vinogradov and R.H. Linnell:Hydrogen Bonding, Van Nostrand Reinhold, New York (1971), Ch.5.

    Google Scholar 

  54. D.S. Allam and W.H. Lee:J. Chem. Soc. 5 (1966).

  55. W.H. Lee:The Chemistry of Non-Aqueous Solvents (Ed. J. J. Logowski) Academic Press, New York (1967).

    Google Scholar 

  56. J. March:Advanced Organic Chemistry: Reaction, Mechanisms, and Structure, McGraw-Hill, New York (1968).

    Google Scholar 

  57. S. Kulstad and L.A. Malmsten:J. Inorg. Nucl. Chem. 4, 1299 (1981).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ganjali, M., Shamsipur, M. A competitive polarographic study of complexation of ammonium, anilinium, hydrazinium and pyridinium ions with some macrocyclic ligands in binary ethanol-water mixtures using a Pb(II)/Pb(Hg) couple as an electrochemical probe. J Incl Phenom Macrocycl Chem 23, 41–51 (1995). https://doi.org/10.1007/BF00706948

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00706948

Key words

Navigation