Skip to main content
Log in

pH-metric studies of acid–base equilibria on the mixed M(II) complexes with R-3-[-1-hydroxy-2(methylamino)ethyl]phenol and some selected carboxylic acids

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Some new ternary complexes’ [Cu(II), Ni(II), Co(II), and Zn(II)] metal ions with phenylephrine and some selected carboxylic acid were investigated by means of potentiometry techniques at 25 °C and in I = 0.10 mol L−1 NaNO3. The protonation equilibria of phenylephrine and biologically important aliphatic and aromatic carboxylic acids: adipic, succinic, malic, tartaric, oxalic, phthalic, and salicylic were investigated and discussed. The acidity constants of the ligand under study were determined and used for determining the stability constants of the binary and ternary complexes formed in the aqueous medium under the experimental conditions. The order of stability constants of binary and ternary complexes was found to obey Co(II) < Ni(II) < Cu(II) > Zn(II). The ternary complex formation was found to occur in a stepwise manner. Extrastability of ternary complexes compared to their binary complexes was explained to be due to electrostatic interactions of the side chains of ligands, charge neutralization, chelate effect, stacking interactions, and hydrogen bonding. The relative stabilities of the ternary complexes are compared with those of the corresponding binary complexes in terms of (ΔlogK, \(\log X\) and % R. S) values. The concentration distribution of the various complex species in solution was evaluated and discussed.

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

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Scheme 2
Fig. 2
Fig. 3
Scheme 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. C. Moffat, J.V. Jackson, M.S.D. Moss, Clarke’s Isolation and Identification of Drugs (The pharmaceutical press, London, 1986)

    Google Scholar 

  2. T.N. Al-Sabha, Pak. J. Anal. Environ. Chem. 1, 1 (2010)

    Google Scholar 

  3. A.Y. Louie, T.J. Meade, Chem. Rev. 99, 2711 (1999)

    Article  CAS  Google Scholar 

  4. R.N. Patel, N. Singh, K. Shukla, U.K. Chauhan, S. Chakraborty, J.N. Gutierrez, A. Castineiras, J. Inorg. Biochem. 98, 231 (2004)

    Article  Google Scholar 

  5. A.H. Fairlamb, G.B. Henderson, A. Cerami, Proc. Natl. Acad. Sci. USA 86, 2607 (1989)

    Article  CAS  Google Scholar 

  6. Z. Balcarova, J. Kasparakova, A. Zakovska, O. Novakova, M.F. Sivo, G. Natile, V. Brabeck, Mol. Pharmacol. 53, 846 (1998)

    CAS  Google Scholar 

  7. R.L. La Femina, J. Virol. 66, 7414 (1992)

    Google Scholar 

  8. P.S. Moore, C.J. Jones, J. Biochem. 307, 129 (1995)

    CAS  Google Scholar 

  9. O. Rixe, W. Ortuzar, M. Alvarez, R. Parker, E. Reed, K. Paull, T. Fojo, Biochem. Pharmacol. 52, 1855 (1996)

    Article  CAS  Google Scholar 

  10. R. Bakhtiar, E.I. Ochiai, Gen. Pharmacol. 32, 525 (1999)

    Article  CAS  Google Scholar 

  11. H.H. Hammud, G. Nemer, W. Sawma, J. Touma, P. Barnabe, Y. Bou-Mouglabey, A. Ghannoum, J. El-Hajjar, J. Usta, Chem. Biol. Interact. 173, 84 (2008)

    Article  CAS  Google Scholar 

  12. E. Martell, R.M. Smith, Critical Constants-1: Amino acids (New York, 1974)

  13. H. Sigel, Metal Ions in Biological Systems-2 (Marcel-Dekker Inc, New York, 1973)

    Google Scholar 

  14. M.T. Beck, Chemistry of Complex Equilibria, (Van Nostrand, New York, 1970) p. 174

  15. A.L. Lehninger, Phys. Rev. 30, 393 (1950)

    CAS  Google Scholar 

  16. F.M. Richards, H.M. Wyckoff, N.M. Allewel, Neurosciences 901, (1969)

  17. W.R. Harris, L. Messori, Coord. Chem. Rev. 228, 237 (2002)

    Article  CAS  Google Scholar 

  18. P.J. Sadler, Z. Gun, Pure Appl. Chem. 70, 863 (1998)

    Article  CAS  Google Scholar 

  19. P.J. Sadler, Adv. Inorg. Chem. 36, 1 (1991)

    Article  CAS  Google Scholar 

  20. M.J. Abrams, B.A. Murrer, Science 261, 725 (1993)

    Article  CAS  Google Scholar 

  21. A.E. Martell, M. Calvin, Chemistry of Metal Chelate Compounds (Prentie Hall, Inc., Englad, Cliffs, N.J., 1962)

    Google Scholar 

  22. R.A. Ammar, A. Nafady, M.F. Amin, M.M. Al-Mogren, M.E. Shoukry, Int. J. Electrochem. Sci. 8, 1501 (2013)

    CAS  Google Scholar 

  23. A.K. Banerjee, T.V. Rao, J. Indian Chem. Soc. 63, 480 (1968)

    Google Scholar 

  24. H. Irving, R.J.P. William, J. Chem. Soc 3192 (1953)

  25. F.J. Welcher, The Analytical Uses of Ethylenediaminetetraacetic Acid (Von Nostrand, Princeton, NJ, 1965)

    Google Scholar 

  26. H.M. Irving, H.S. Rossotti, J. Chem. Soc 3397, 2904 (1953–1954)

  27. P. Gans, O. Sullivan, B. Glee, Talanta 51, 33 (2000)

    Article  CAS  Google Scholar 

  28. P. Gans, A. Sabatini, Vacca. Talanta 43, 1739 (1996)

    Article  CAS  Google Scholar 

  29. R.G. Bates, Determination of pH-Theory and Practice, 2nd edn. (Wiley-Interscience, New York, 1975)

    Google Scholar 

  30. SC Database; Royal Society of Chemistry; IUPAC: 2004. http://www.Acadsoft.Co.uk/

  31. R. Cornelis, J. Caruso, H. Crews, K. Heumann, Handbook of Elemental Speciation: Techniques and Methodology (Wiley, New York, 2003)

    Book  Google Scholar 

  32. M.M. Shoukry, A.A. Shoukry, P.A.K. Alla, S.S. Hassan, Int. J. Chem. Kinet. 42, 608 (2010)

    Article  CAS  Google Scholar 

  33. J. Inezedy, Determination of equilibrium constants, in Analytical Applications of Omplex Equilibria, ed. by S. Ellis (Ellis Howard, Chichester, UK, 1967)

    Google Scholar 

  34. R.M. Smith, A.E. Martell, NIST critically selected stability constants of metal complexes database, Version 3.0. NIST Standard Reference Database 46, U.S. Department of Commerce, (National Institute of Standard and Technology (1997)

  35. A.A. Boraei, N.F.A. Mohamed, J. Chem. Eng. 47, 987 (2002)

    CAS  Google Scholar 

  36. M.M. Shoukry, S.M.T. Ezzat, Bioinorgan. Chemistry Appl 1 (2014)

  37. H.A. Azab, A.M. Nady, A. Hassan, R.S.A. Azkal, J. Chem. Eng 38, 502 (1993)

    CAS  Google Scholar 

  38. R. Weast, Handbook of Chemistry and Physics, 68th edn. (CRC Press, Boca Raton, FL, 1987)

    Google Scholar 

  39. M.F. Amin, J. Chem. Chem. Eng. 7, 591 (2013)

    CAS  Google Scholar 

  40. H.A. Ewais, M. Taha, H.N. Salm, J. Chem. Eng. Data 55, 754 (2010)

    Article  CAS  Google Scholar 

  41. B. Humbert, M. Alnot, F. Quile`s, F. Infrared, A. Raman, J. Chromatogr. 54, 465 (1998)

    Google Scholar 

  42. F. Mack, H. Bonisch, Naunyn-Schmiedeberg’s Arch. Pharmacol 310, 1 (1979)

    Article  CAS  Google Scholar 

  43. M. Meloun, T. Syrový, A. Vrána, Anal. Chem. Acta 533(1), 97 (2005)

    Article  CAS  Google Scholar 

  44. S. Riegelman, L.A. Strait, E.Z. Fischer, J. Pharm. Sci. 51, 2 (1962)

    Google Scholar 

  45. H.A. Azab, A.M. Nady, A. Hassan, R.S.A. Azkal, Monatsshefte fṻr Chemie 124, 267 (1993)

    Article  CAS  Google Scholar 

  46. G.V. Mane, D.G. Kolhatkar, L.P. Shinde, J. Chem. Pharm. Res. 4(2), 1022 (2012)

    CAS  Google Scholar 

  47. P.D. Manwel, Asian J. Chem. 6(2), 408 (1994)

    Google Scholar 

  48. S.A.A. Sajadi, Adv. Biosc. Biotechnol. 1, 354 (2010)

    Article  Google Scholar 

  49. M.M. Khalil, A. Radalla, F. Qasem, R. Khaled, J. Korean Chem. Soc. 31(1), 109 (2014)

    Article  CAS  Google Scholar 

  50. K. Irving, R.P. Williams, Nature (London) 162, 746 (1948)

    Article  CAS  Google Scholar 

  51. H.M.N.H. Irving, R.J.P. Williams, The stability of transition-metal complexes. J. Chem. Soc. (pp. 3192–3210, 1952)

  52. J.E. Huheey, Inorganic Chemistry-Principles of Structure and Reactivity (Harper, New York, NY, USA, 1983)

    Google Scholar 

  53. F.A. Cotton, G. Wilkinson, Advaned Inorganic Chemistry (Wiley, London, UK, 1962)

    Google Scholar 

  54. C.S.G. Phillips, R.J.P. Williams, Inorganic Chemistry: Metals, vol. 2 (Oxford University Press, New York, NY, USA, 1966)

    Google Scholar 

  55. H. Sigel, Angew. Chem. Int. Edn. 14, 394 (1975)

    Article  Google Scholar 

  56. H. Sigel, B.E. Fischer, E. Farkas, Inorg. Chem. 22, 925 (1983)

    Article  CAS  Google Scholar 

  57. B.E. Fischer, H. Sigel, Inorg. Chem. 18(2), 425 (1979)

    Article  CAS  Google Scholar 

  58. R.B. Martin, R.J. Prados, J. Inorg. Nucl. Chem. 36, 1665 (1974)

    Article  CAS  Google Scholar 

  59. G.F. Condike, A.E. Martell, J. Inorg. Nucl. Chem. 31, 2455 (1969)

    Article  CAS  Google Scholar 

  60. S. Singh, A.K. Ghose, J. Indian Chem. Soc. 73, 650 (1996)

    CAS  Google Scholar 

  61. S. Tyagi, S. Gencaslan, U.P. Singh, J. Chem. Eng. Data 48, 925 (2003)

    Article  CAS  Google Scholar 

  62. R. Dewitt, J.L. Watters, J. Am. Chem. Soc. 76, 3810 (1954)

    Article  CAS  Google Scholar 

  63. S. Kida, Bull. Chem. Soc. Jpn. 29, 805 (1956)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Rehab Khaled Mahmoud.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khalil, M.M., Mahmoud, R.K. pH-metric studies of acid–base equilibria on the mixed M(II) complexes with R-3-[-1-hydroxy-2(methylamino)ethyl]phenol and some selected carboxylic acids. J IRAN CHEM SOC 12, 1149–1161 (2015). https://doi.org/10.1007/s13738-014-0576-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-014-0576-6

Keywords

Navigation