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Potentiometric Studies on Binary and Ternary Complexes of Ni(II) and Cu(II) Ions with L-Valine and Paracetamol

Year 2023, , 325 - 338, 31.05.2023
https://doi.org/10.18596/jotcsa.1140039

Abstract

The protonation constants of the free ligands and the stability constants of binary and ternary complexes of bivalent metal ions of Ni(II) and Cu(II) with a biologically important amino acid of L-valine, Val, and paracetamol, Para, were studied potentiometrically in aqueous solutions at 313.15 ± 0.1 K and a fixed ionic strength of I = 0.10 M NaCl. The complexation model for each system was established using the Irving-Rossotti equation. The formation of the 1:2 or 1:1 binary complexes and 1:1:1 ternary complexes in which the amino acid Val was used as the primary ligand and Para as the secondary ligand, as inferred from the corresponding potentiometric pH-metric titration curves, and their relative stabilities compared to the corresponding ML and ML2 binary complexes are expressed in terms of statistical parameters ∆logK, logK1 and logK2. The complex stability was found to follow the order of Cu(II) > Ni(II). Through these diagnostic studies, it was possible to give the general formula of compounds prepared from amino acids and paracetamol. Amino acid binds to the central ion through oxygen in the hydroxyl group and nitrogen atom in the amine group (-NH2), whereas paracetamol forms a unipolar bond by binding to the concentrated ion through the oxygen atom in the hydroxyl group. Most of the nickel complexes had octahedral symmetry with valine and paracetamol ligands, while the copper complexes had square or hierarchical to square base symmetry.

Supporting Institution

CHEMISTRYDEPARTEMENT

Thanks

SEBHA UNIVERSITY

References

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Year 2023, , 325 - 338, 31.05.2023
https://doi.org/10.18596/jotcsa.1140039

Abstract

References

  • 1. Myers R. The basics of chemistry. Greenwood Publishing Group; 2003.
  • 2. Crabb E, Moore E. Metals and Life Chapter 9. RSC Publishing; 2010.
  • 3. Jones C, Thornback JR. Medicinal Applications of Coordination Chemistry. RSC Publishing; 2007.
  • 4. Alexandrova R, Rasshkova G, Alexandrov I, Tsenova W, Tudose R, Costisor O. Briefly about copper. Exp Pathol Parasitol. 2003;1311:6851.
  • 5. Malmström BG, Leckner J. The chemical biology of copper. Curr Opin Chem Biol [Internet]. 1998 Apr 1;2(2):286–92.
  • 6. Coleman N, Castrejon A, Blaine C, Chemmachel T. The toxicology of essential and nonessential metals. 2017.
  • 7. Smith RM, Motekaitis RJ, Martell AE. Prediction of stability constants. II. Metal chelates of natural alkyl amino acids and their synthetic analogs. Inorganica Chim Acta [Internet]. 1985 Sep 2;103(1):73–82.
  • 8. Gergely A, Nagypál I, Farkas E. Thermodynamic relations of parent and mixed complexes of asparagine and glutamine with copper(II). J Inorg Nucl Chem [Internet]. 1975 Feb 1;37(2):551–5.
  • 9. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature and symbolism for amino acids and peptides. Recommendations 1983. Biochem J [Internet]. 1984 Apr 15;219(2):345–73.
  • 10. Lynch CJ, Adams SH. Branched-chain amino acids in metabolic signalling and insulin resistance. Nat Rev Endocrinol [Internet]. 2014 Dec 7;10(12):723–36.
  • 11. Belkher NA, Al-Abbas AA, Zidan M. Potentiometric Studies on Stability Constant of the Complexes of Some Essential Transition Metal Ions with L-Valine. J Pure Appl Sci [Internet]. 2019 May 1;18(3):59–63.
  • 12. Sigel A, Sigel H, Sigel, Roland KO. Nickel and its surprising impact in nature. Metal Ions in Life Sciences, Volume 2 [Internet]. England: Wiley; 2007. 728pp p.
  • 13. Wieser ME, Holden N, Coplen TB, Böhlke JK, Berglund M, Brand WA, et al. Atomic weights of the elements 2011 (IUPAC Technical Report). Pure Appl Chem [Internet]. 2013 Apr 30;85(5):1047–78.
  • 14. Wiberg E, Wiberg N, Holleman A. Inorganic chemistry. Academic Press; 2001. 1665 p.
  • 15. Harris ED. Copper Homeostasis: The Role of Cellular Transporters. Nutr Rev [Internet]. 2001 Apr 27;59(9):281–5.
  • 16. Groff JL, Gropper SS, Hunt SM. Advanced nutrition and human metabolism. St. Paul Minneapolis: West Publishing Company. 1995.
  • 17. Araya M, Pizarro F, Olivares M, Arredondo M, Gonzalez M, Mendez M. Understanding copper homeostasis in humans and copper effects on health. Biol Res [Internet]. 2006;39(1):183–7.
  • 18. Bowman WC, Rand MJ. Textbook of pharmacology. Blackwell Scientific Publications; 1980.
  • 19. Negwer M. Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH; 2001. 4880 p.
  • 20. Alhalib A. Spectrophotometric determination of acetaminophen content of different brands of paracetamol tablets from Zliten. J Alasmarya Univ [Internet]. 2017;2(2):134–40.
  • 21. Van Boxtel CJ, Santoso B, Edwards IR. Drug benefits and risks: International textbook of clinical pharmacology-revised 2nd edition. Ios Press; 2008.
  • 22. Goodman LS. Goodman and Gilman’s The Pharmacological Basis of Therapeutics. New York: Mcgraw-Hill; 1996.
  • 23. Singh Sandhu R, Kumar Kalia R. Complexation reaction of metal ions with peptide systems. VII. Equilibrium studies of N-benzoyl-L-valine, N-benzoyl-glycyl-L-valine and isovaleric acid with metal(II) ion systems. Thermochim Acta [Internet]. 1980 Sep 15;40(2):305–9.
  • 24. Enamullah M, Ahmed MG, Akhtar F. Meters of Divalent Zinc, Nickel, Cobalt and Cadmium Complexes of Phthalic Acid. J Bangladesh Chem Soc. 1991;4(2):129–36.
  • 25. Mendes J, de Almeida KJ, Neto JL, Ramalho TC, Duarte HA. Theoretical spectroscopic insights of tautomers and enantiomers of penicillamine. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2017 Sep 5;184:308–17.
  • 26. Mackay D. The reaction of thiol amino acids with pyridoxal 5′-phosphate in the absence and in the presence of l-glutamic acid. Biochim Biophys Acta - Spec Sect Enzymol Subj [Internet]. 1963 Jul 9;73(3):445–53.
  • 27. Ash T, Debnath T, Ghosh A, Das AK. Comprehensive understanding of multiple binding of D-penicillamine with Cu2+-hexa aqua complex: a DFT approach. Struct Chem [Internet]. 2020 Feb 4;31(1):155–69.
  • 28. Chakrawarti PB, Chakrawarti M, Maini P. Equilibrium studies of ternary chelates of some divalent metal ions with cephalosporins and α-alanine. J Indian Chem Soc. 2000 Mar 15;77(5):217–9.
  • 29. Suhud K, Heng LY, Rezayi M, Al-abbasi AA, Hasbullah SA, Ahmad M, et al. Conductometric Studies of the Thermodynamics for Complexation of 1,1-Diethyl-3-(4-methoxybenzoyl)thiourea and Cobalt(II) Cation in Aqueous Binary Mixtures of Polar Organic Solvents. J Solution Chem [Internet]. 2015 Feb 22;44(2):181–92.
  • 30. Tan SS, Al-abbasi AA, Mohamed Tahir MI, Kassim MB. Synthesis, structure and spectroscopic properties of cobalt(III) complexes with 1-benzoyl-(3,3-disubstituted)thiourea. Polyhedron [Internet]. 2014 Jan 28;68:287–94.
  • 31. Al-abbasi AA, Mohamed Tahir MI, Kassim MB. 1,1-Diethyl-3-(4-methoxybenzoyl)thiourea. Acta Crystallogr Sect E [Internet]. 2011 Dec 15;E67:o3414.
  • 32. Al-abbasi AA, Kassim MB. 1-Ethyl-1-methyl-3-(2-nitrobenzoyl)thiourea. Acta Crystallogr Sect E [Internet]. 2011 Jul 15;E67:o1840.
  • 33. Al-abbasi AA, Tan SS, Kassim MB. 1-Benzoyl-3-(4-hydroxyphenyl)thiourea. Acta Crystallogr Sect E Struct Reports Online [Internet]. 2010 Dec 15;E66:o3181.
  • 34. Al‐abbasi AA, Tahir MIM, Kayed SF, Kassim MB. Synthesis, characterisation and biological activities of mixed ligand oxovanadium (IV) complexes derived from N , N ‐diethyl‐ N ′‐ para ‐substituted‐benzoylthiourea and hydrotris(3,5‐dimethylpyrazolyl)borate. Appl Organomet Chem [Internet]. 2022 Apr 1;36(4):e6607.
  • 35. Almutaleb AAA, Alabbasi AA. Synthesis, characterization and computational studies for (2′ S *,3 R *,3′ S *,8a′ R *)‐2′,3′‐bis(ethoxycarbonyl)‐2‐oxo‐2′,3′‐dihydro‐8a′H‐spiro[indoline‐3,1′‐indolizine]‐6′‐carboxylic acid and some derivatives. J Phys Org Chem [Internet]. 2023 Feb 27;36(2):e4452.
  • 36. Bjerrum J. Metal ammine formation in aqueous solution: Theory of the reversible step reactions. 1957. 296 p.
  • 37. Bjerrum J. Stability Constants of Metal-Ion Complexes with Solubility Products of Inorganic Substances. Stability Constants of Metal-Ion Complexes. Section I: Inorganic Ligands. Compiled by Lars Gunnar Sillén. Section II: Organic Ligands. Compiled by Arthur E. Marte [Internet]. London : Chemical society; 1964.
  • 38. Irving H, Williams RJP. The stability of transition-metal complexes. J Chem Soc [Internet]. 1953 Jan 1;3192–210.
  • 39. Irving HM, Rossotti HS. The calculation of formation curves of metal complexes from pH titration curves in mixed solvents. J Chem Soc [Internet]. 1954 Jan 1;2904–10.
  • 40. Bretti C, Giuffrè O, Lando G, Sammartano S. Modeling solubility and acid–base properties of some amino acids in aqueous NaCl and (CH3)4NCl aqueous solutions at different ionic strengths and temperatures. Springerplus [Internet]. 2016 Dec 30;5(1):928.
  • 41. Juela DM. Comparison of the adsorption capacity of acetaminophen on sugarcane bagasse and corn cob by dynamic simulation. Sustain Environ Res [Internet]. 2020 Dec 1;30(1):23.
  • 42. Doğan A, Kılıç E. Potentiometric studies on the stability constants of some-amino acid-copper (II) and nickel (II) systems in ethanol-water mixture. Indian J Chem - Sect A Inorganic, Phys Theor Anal Chem. 2003;42(7):1632–5.
  • 43. Snyder RV. A Study of Stereoselective Amino Acid Complexes of Copper(II) and Nickel(II) [Internet]. Doctoral Theses. [United States -- Iowa]: Iowa State University; 1972.
  • 44. Zine AM. Ni(II)-Mercaptosuccinic Acid/2-Mercaptopropionyl Glycine-Amino Acids Ternary Complexes-A potentiometric Study. Int J Chem Sci. 2005;3(2):295–300.
  • 45. Smith PK, Taylor AC, Smith ERB. Thermodynamic properties of solutions of amino acids and related substances. J Biol Chem [Internet]. 1937 Dec;122(1):109–23.
  • 46. Belkher NA, Al-Abbas AA, Zidan M. Potentiometric Studies on Stability Constant of the Complexes of Some Essential Transition Metal Ions with L-Valine. J Pure Appl Sci [Internet]. 2019;18(3):59–63.
  • 47. Angelici RJ, Allison JW. Stability constants for amino acid coordination by substituted diethylenetriamine complexes of copper(II) and the kinetics of amino acid ester hydrolysis. Inorg Chem [Internet]. 1971 Oct 1;10(10):2238–43.
  • 48. Magare BK, Ubale MB. Equilibrium Studies on Ternary Metal Complexes of Drug Ethambutol Hydrochloride with Nickel and Cobalt Metal Ions and Four Amino Acids. Int Res J Eng Technol [Internet]. 2008;6(8):1280–4.
  • 49. Rajarajan G, Dhineshkumar E, Amala S, Seenivasan M, Paramasivan A. Determination of Stability constants Nickel binary and ternary complexes in aquesous DMSO by Pontentiometric method. J Phys Conf Ser [Internet]. 2021 Jan 1;1724(1):012005.
  • 50. Chandrathilaka A, Ileperuma O, Hettiarachchi C. Spectrophotometric and pH-metric studies on Pb(II), Cd(II), Al(III) and Cu(II) complexes of paracetamol and ascorbic acid. J Natl Sci Found Sri Lanka [Internet]. 2013 Dec 12;41(4):337–44.
  • 51. O’Neil MJ, Heckelman PE, Koch CB, Roman KJ. The Merck Index, 14th edition. Merck, John Wiley & Sons, Inc.; 2006.
  • 52. Patil A. Stability constants of binary and ternery complexes of ibuprofen and paracetamol. Rasayan J Chem [Internet]. 2013;6(3):168–71.
  • 53. Kaur H, Singla A. Comparative study of stability constants and thermodynamic properties of complexation of Aspirin and Paracetamol with divalent metal ions by potentiometry. Int J Theor Appl Sci. 2010;2(1):14–7.
  • 54. Sovago I, Kiss T, Gergely A. Critical survey of the stability constants of complexes of aliphatic amino acids (Technical Report). Pure Appl Chem [Internet]. 1993 Jan 1;65(5):1029–80.
  • 55. Li NC, White JM, Yoest RL. Some Metal Complexes of Glycine and Valine 1. J Am Chem Soc [Internet]. 1956 Oct 1;78(20):5218–22.
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There are 72 citations in total.

Details

Primary Language English
Subjects Inorganic Chemistry
Journal Section RESEARCH ARTICLES
Authors

Aisha Alabbası 0000-0002-6082-9246

Nouria Ali Belkher This is me

Khadija Ahmida This is me

Mohamed Zidan This is me

Publication Date May 31, 2023
Submission Date July 3, 2022
Acceptance Date February 2, 2023
Published in Issue Year 2023

Cite

Vancouver Alabbası A, Belkher NA, Ahmida K, Zidan M. Potentiometric Studies on Binary and Ternary Complexes of Ni(II) and Cu(II) Ions with L-Valine and Paracetamol. JOTCSA. 2023;10(2):325-38.