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Potentiometric Studies on Complexation of Cu(II) Ion with Methyl/Nitro-Substituted 1,10-Phenanthrolines and Selected Amino Acids

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Abstract

Protonation constants of methyl/nitro substituted 1,10-phenanthrolines {(m/n-sphen): 4-methyl-phenanthroline (4-mphen), 5-methyl-1,10-phenanthroline (5-mphen), 4,7-dimethyl-1,10-phenanthroline (dmphen), 3,4,7,8-tetramethyl-1,10-phenanthroline (tmphen) and 5-nitro-1,10-phenanthroline (5-nphen)] and the amino acids (aa) l-tyrosine (tyr) and glycine (gly), and their corresponding binary and ternary stability constants with Cu(II), were determined in aqueous 0.1 mol·L−1 KCl ionic media at 298.15 K. The protonation constants of the ligands and the stability constants of the binary and ternary complexes of Cu(II) with the ligands were calculated from the potentiometric data using the “BEST” software package. The species distribution diagrams were obtained using the “SPE” software package under the experimental conditions described. The order of stability of the ternary complexes in terms of the primary ligands is [Cu(tmphen)(aa)]+ > [Cu(dmphen)(aa)]+ > [Cu(4-mphen)(aa)]+ > [Cu(5-mphen)(aa)]+ > [Cu(5-nphen)(aa)]+. The stability constants of the ternary complexes decrease in the following order: [Cu(m/n-sphen)(gly)]+ > [Cu(m/n-sphen)(tyr)]+, which is identical to the sequence found for the binary complexes of Cu(II) with gly and tyr.

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References

  1. Kaim, W., Schwederski, B.: Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life. Wiley, New York (1996)

    Google Scholar 

  2. McBryde, W.A.E., Brisbin, D.A., Irving, H.: 1004. The stability of metal complexes of 1,10-phenanthroline and its analogues. Part III. 5-Methyl-1,10-phenanthroline. J. Chem. Soc., 5245–5253 (1962)

  3. Irwing, H., Mellor, D.H.: 1003. The stability of metal complexes of 1,10-phenanthroline and its analogues. Part II. 2-Methyl- and 2,9-dimethyl-phenanthroline. J. Chem. Soc. 5237–5245 (1962)

  4. Irwing, H., Mellor, D.H.: 1002. The stability of metal complexes of 1,10-phenanthroline and its analogues. Part I. 1,10-Phenanthroline and 2,2′-bipyridyl. J. Chem. Soc. 5222–5237 (1962)

  5. İnci, D., Aydın, R., Yılmaz, D., Gençkal, H.M., Vatan, O., Çinkılıç, N., Zorlu, Y.: New water-soluble copper(II) complexes including 4,7-dimethyl-1,10-phenanthroline and l-tyrosine: synthesis, characterization, DNA interactions and cytotoxicities. Spectrochim. Acta A. 136(Part B), 761–770 (2015)

    Google Scholar 

  6. İnci, D., Aydın, R., Vatan, O., Yılmaz, D., Gençkal, H.M., Zorlu, Y., Cavaş, T.: Binary and ternary new water soluble copper(II) complexes of l-tyrosine and substituted 1,10-phenanthrolines: effect of substitution on DNA interactions and cytotoxicities. Spectrochim. Acta A 145, 313–324 (2015)

    Article  Google Scholar 

  7. Garret, R.H., Grisham, C.M.: Biochemistry. Sanders, New York (1995)

    Google Scholar 

  8. İnci, D., Aydın, R., Zorlu, Y.: Affinity of a new copper(II) complex to DNA/BSA andantioxidant/radical scavenging activities: crystal structure of [Cu(4,7-diphenyl-1,10-phenanthroline)(leucine)(NO3)(H2O)]. J. Coord. Chem. 69, 2677–2696 (2016)

    Article  Google Scholar 

  9. Aydın, R., Yırıkoğulları, A.: Potentiometric study on complexation of divalent transition metal ions with amino Acids and adenosine 5′-triphosphate. J. Chem. Eng. Data 55, 4794–4800 (2010)

    Article  Google Scholar 

  10. İnci, D., Aydın, R.: Stabilities of the ternary complexes of copper(II) with substituted 1,10-phenanthrolines and some amino acids in aqueous solution. J. Solution Chem. 43, 711–726 (2014)

    Article  Google Scholar 

  11. Aydın, R., Serbest, Z., Özer, U.: Formation of the complexes between lanthanum(III) ion and 5-sulfosalicylate,5-nitrosalicylate. Rev. Inorg. Chem. 25, 271–283 (2005)

    Google Scholar 

  12. Aydın, R.: Study on the interaction of yttrium(III) with adrenaline, noradrenaline, and dopamine. J. Chem. Eng. Data 52, 2400–2404 (2007)

    Article  Google Scholar 

  13. Aydın, R., İnci, D.: Potentiometric and spectrophotometric studies of the complexation of lanthanum(III) with adrenaline, noradrenaline, and dopamine. J. Chem. Eng. Data 57, 967–973 (2012)

    Article  Google Scholar 

  14. Martell, A.E., Motekaites, R.J.: Determination and Use of Stability Constants. VCH Publishers, New York (1989)

    Google Scholar 

  15. Schwarzenbach, G., Flaschka, A.: Complexometric Titrations. Methuen, New York (1969)

    Google Scholar 

  16. Gran, G.: Determination of the equivalent point in potentiometric titrations. Acta Chem. Scand. 4, 559–577 (1950)

    Article  CAS  Google Scholar 

  17. Rossotti, F.J.C., Rossotti, H.: Potentiometric titrations using Gran plots. J. Chem. Educ. 42, 375–378 (1965)

    Article  CAS  Google Scholar 

  18. Soliman, A.A., El-Sherif, A.A., Amin, M.A.: Thermodynamics, chemical speciation and complex formation equilibria studies of binary and mixed ligand complexes of Cu(II) with 2,2′-bipyridyl and some aromatic diamines. J. Solution Chem. 44, 77–99 (2015)

    Article  CAS  Google Scholar 

  19. Brandt, W.W., Gullstrom, D.K.: Studies on some ferrous complexes of substituted 1,10-phenanthrolines. J. Am. Chem. Soc. 74, 3532–3535 (1952)

    Article  CAS  Google Scholar 

  20. The stability of metallic complexes of two dimethyl-phenanthrolines: Brisbin, D.A., MCbryde, W.A.E. Can. J. Chem. 41, 1135–1141 (1963)

    Article  Google Scholar 

  21. Schilt, A.A., Smith, G.F.: Acid dissociation constants of substituted 1,10-phenanthrolines. J. Phys. Chem. 60, 1546–1548 (1956)

    Article  CAS  Google Scholar 

  22. Demirelli, H., Köseoğlu, F.: Equilibrium studies of Schiff bases and their complexes with Ni(II), Cu(II) and Zn(II) derived from salicylaldehyde and some α-amino acids. J. Solution Chem. 34, 561–577 (2005)

    Article  CAS  Google Scholar 

  23. Tanaka, M., Tabata, M.: Stability constants of metal(II) complexes with amines and aminocarboxylates with special reference to chelation. Bull. Chem. Soc. Jpn. 82, 1258–1265 (2009)

    Article  CAS  Google Scholar 

  24. Banks, C.V., Bystroff, R.I.: Stability orders in transition metal-1,10-phenanthroline complexes. J. Am. Chem. Soc. 81, 6153–6158 (1959)

    Article  CAS  Google Scholar 

  25. Sigel, H.: Ternary Cu2+ complex: stability, structure and reactivity. Angew. Chem. Int. Ed. Engl. 14, 394–402 (1975)

    Article  Google Scholar 

  26. Patel, P.J., Patel, V.K., Bhattachanya, P.K.: Effect of two ligands on ternary complex stability. Inorg. Chem. 21, 3163–3166 (1982)

    Article  CAS  Google Scholar 

  27. Watanabe, S., Saito, T.: Circular dichroism and ultraviolet studies of the cupric(II) and nickel(II)–3,4-dihydroxyphenylalanine complex. J. Inorg. Biochem. 58, 147–155 (1995)

    Article  CAS  Google Scholar 

  28. Yamauchi, O., Sakurai, T., Nakahara, A.: Stereo selectivity in mixed ligand copper(II) complexes with electrostatic ligand–ligand interactions. Application to optical resolution of α-amino acids with a charged side chain. Bull. Chem. Soc. Jpn. 50, 1776–1779 (1977)

    Article  CAS  Google Scholar 

  29. Sakurai, T., Yamauchi, O., Nakahara, A.: Mixed ligand copper(II) complexes of α-amino acids with ligand–ligand interactions. Bull. Chem. Soc. Jpn. 49, 169–173 (1976)

    Article  CAS  Google Scholar 

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Acknowledgements

We thank the Research Fund of Uludag University for the financial support given to the research project (Project Numbers OUAP (F)-2015/14) and the Scientific and Technological Research Council of Turkey (TUBITAK) for a Domestic PhD Scholarship intended for priority areas of the first author (Code: 2211-C). This study is a part of a doctoral thesis in progress of the first author at the Graduate School of Natural and Applied Sciences of Uludag University.

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  1. Department of Chemistry, Faculty of Arts and Sciences, Uludag University, 16059, Bursa, Turkey

    Duygu İnci & Rahmiye Aydın

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  1. Duygu İnci
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  2. Rahmiye Aydın
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Correspondence to Rahmiye Aydın.

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İnci, D., Aydın, R. Potentiometric Studies on Complexation of Cu(II) Ion with Methyl/Nitro-Substituted 1,10-Phenanthrolines and Selected Amino Acids. J Solution Chem 46, 124–138 (2017). https://doi.org/10.1007/s10953-016-0551-1

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