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Asian Journal of Chemistry Asian Journal of Chemistry Asian Journal of Chemistry; Vol. 26, No. 8 (2014), 2395-2399 ASIAN JOURNAL OF CHEMISTRY http://dx.doi.org/10.14233/ajchem.2014.16023 Determination of Stability Constants of Mixed Ligand Complexes of Picolinic Acid and Other Bioactive Ligands with Zn(II) by Potentiometric Titration Method 1 1,2,* 1 NADA M. ARISHY , REDA A. AMMAR and ABDULRHMAN AL-WARTHAN 1Department of Chemistry, College of Science, King Saud University, P.O. Box 22452, Riyadh 11495, Saudi Arabia 2Department of Chemistry, College of Science, Al Azhar University, Cairo, Egypt *Corresponding author: E-mail: [email protected] Received: 9 July 2013; Accepted: 5 November 2013; Published online: 15 April 2014; AJC-15033 The stability constants of ternary complexes of Zn(II) with picolinic acid as primary ligand and some of bioactive ligands (e.g., amino acids and peptides) as secondary ligand were determined pH-metrically at 25 °C and ionic strength 0.1 mol/L NaNO3 in water solution. The possible formation of ternary complexes via simultaneous mechanisms has been confirmed by comparison with constructed theoretical curves. The stability of each ternary complexes was also investigated and compared with those of the corresponding binary complexes in terms of the ∆ log K parameter. In addition, the concentration distribution of the complexes formed in solution was evaluated. Keywords: Picolinic acid, Mixed ligand complexes, ∆∆∆ log K, Stability constants, Potentiometric studies. INTRODUCTION (amino acid and peptide) with Zn(II) were determined using potentiometric titration in water solution at 25 °C and an ionic Picolinic acid (P) is, chemically, pyridine-2-carboxalic strength (I) of 0.1 mol/L (NaNO ). acid. It is a six-member ring structure compound (Fig. 1) that 3 has been detected in a many of the biological systems1. The EXPERIMENTAL picolinic acid is present in many natural products and acts as All chemicals in this work were of guaranteed grade and a bidentate ligand by (N, COO-) coordination for many metal used without further purification. Picolinic acid was obtained 2 3 4 5 ions . Examples include, cobalt(III) , copper(II) , chromium(VI) , from sigma. All the amino acids, related compounds and peptides 6 7 8 manganese(II) , vanadium(III) and palladium(II) . Metallic used are glycine, alanine, valine, proline, β-phenylalanine, complexes of picolinic acid have received increasing attention methionine, isoleucine, glutamic acid, threonine, serine, 2 in last few decades because of their variety applications in ornithine, cysteine, histidine, histamine-2HCl, pencill-amine, 9 the chemical and pharmaceutical industry . For example, imidazole, mercaptoethanol methylamine, glycyl glycine, chromium picolinate increases and regulates the secretion of glycinamide and glutamine were provided by BDH-Bioche- 10,11 insulin . Also, zinc picolinate has a healing effect against micals Ltd. The zinc content of solutions was determined by 12 herpes simplex virus . complexometric EDTA titrations15. Threonine, serine, ornithine, cysteine, histidine and pencillamine solutions were prepared in HO the protonated form by dissolution in two equivalents of nitric acid. All stock solutions of NaNO3 and HNO3 (Merck) were N prepared in deionized water. Zn(NO3)2·6H2O and NaNO3 were O Fig.1. Structure of picolinic acid provided by BDH-Biochemicals Ltd. The ionic strength of each solution was adjusted to 0.10 mol/L NaNO3. Carbonate-free Furthermore, the stability constants of zinc(II)-picolinic NaOH (titrant) was prepared and standardized against a acid13, zinc(II)-amino acid and zinc(II) peptides complexes14 potassium hydrogen phthalate solution. were previously studied. Until now, there are no reports on All the pH-measurements were performed with a Metrohm the speciation of ternary Zn(II)-picolinic acid complexes with 211 microprocessor (Hanna, Romania) in 0.1 M ionic strength amino acids and peptides by potentiometric titration. In the at 298 K temperature. The microprocessor and electrode were present work, equilibrium and the stability constants of mixed calibrated with standard buffer solutions, prepared according complexes composed of picolinic acid and bioactive ligands to NBS specification16. 2396 Arishy et al. Asian J. Chem. Procedure and measurements: The dissociation constants TABLE-1 of the primary ligand picolinic acid and other ligands were STABILITY CONSTANTS OF BINARY SYSTEMS Zn(II)-P, Zn(II)-L AND PROTON-ASSOCIATION CONSTANTS determined potentiometrically by titrating the ligand (40 mL) AT 25 °C AND I = 0.1 mol; L = NaNO -2 3 solution (1 × 10 mol/L). All titrations, HNO3 solution was System L P q ra b added in this work to ensure full protonation of ligands. The log 10 β formation constant of the binary complex was determined 0 0 1 1 5.22 (0.008) 0 0 1 2 6.74 (0.04) Picolinic acid (P) using potentiometric data obtained from mixtures (40 mL) of 1 0 1 0 5.12 (0.02) -3 zinc ion (5 × 10 mol/L) and the ligand in the concentration 1 0 2 0 9.42(0.03) ratio of 1:1 and 1:2 (zinc:ligand) for picolinic acid, amino 0 0 1 1 9.64 (0.01) acids and peptides. Finally, the stability constants of the ternary 0 0 1 2 12.17 (0.02) Glycine complexes were determined by titrating 40 mL of a solution 1 0 1 0 4.91 (0.01) mixture contained equivalent amounts of zinc(II) ion, picolinic 1 0 2 0 9.37 (0.02) acid and the other ligand (1 × 10-2 mol/L), giving rise to molar 0 0 1 1 9.80 (0.01) 0 0 1 2 12.62 (0.03) ratios of 1:1:1 at I = 0.1 mol/L (NaNO3) at 25 °C in water solution. Alanine 1 0 1 0 4.75 (0.02) Data processing: The stability constants and stoichio- 1 0 2 0 8.76 (0.02) metries of the complex species formed in water solutions were 0 0 1 1 9.68 (0.00) determined through the study of various possible composition 0 0 1 2 12.18 (0.01) Valine models for the systems studied. In this study, all the calculations 1 0 1 0 5.32 (0.02) were performed for the dissociation and the complex formation 1 0 2 0 9.19 (0.03) constants using the computer program HYPERQUAD17 and 0 0 1 1 10.65 (0.009) 0 0 1 2 13.18 (0.01) the speciation as a function of pH using the computer program Proline HYSS18. 1 0 1 0 5.24 (0.03) 1 0 2 0 9.98 (0.05) RESULTS AND DISCUSSION 0 0 1 1 9.20 (0.01) 0 0 1 2 11.81(0.03) β-Phenyl alanine The dissociation constants of the ligands were determined 1 0 1 0 4.57 (0.02) 1 0 2 0 8.25 (0.03) in water solution and under the experimental conditions (25 °C, 0 0 1 1 9.23 (0.02) I = 0.1 mol/L NaNO3), which were also used for determining 0 0 1 2 12.04 (0.04) Methionine the stability constants of the Zn(II) complexes and the results 1 0 1 0 4.37 (0.03) are given in Table-1. 1 0 2 0 8.75 (0.05) Dissociation constants of picolinic acid: The calculated 0 0 1 1 9.82 (0.01) 0 0 1 2 12.46 (0.04) acid dissociation constants of the picolinic acid, expressed as Isoleucine pKa values, were given in Table-1. In acid medium, the first 1 0 1 0 5.29 (0.02) 1 0 2 0 8.97 (0.03) protonation constant refers to the of the pyridine (pKa1 = 5.22) 0 0 1 1 9.46 (0.01) and the second to the carboxylic acid (pKa2 = 1.52). These 0 0 1 2 13.54 (0.01) results obtained are consistent with previous investigations Glutamic acid 19 1 0 1 0 5.70 (0.01) undertaken for related systems . 1 0 2 0 9.74 (0.02) Binary complexes: The titration curve of the Zn(II)-picolinic 0 0 1 1 9.06 (0.009) acid complex is markedly lower than the picolinic acid titration 0 0 1 2 11.07 (0.03) Threonine curve, indicating formation of Zn(II) complexes by displace- 1 0 1 0 4.62 (0.04) ment of protons (Fig. 2). In the binary systems of (Zn(II)- 1 0 2 0 8.59 (0.05) picolinic acid) the selected model with the best statistical fit 0 0 1 1 9.17 (0.01) 0 0 1 2 11.54 (0.03) was found to consist of Zn(picolinic acid) and Zn(picolinic Serine 1 0 1 0 4.57 (0.01) acid)2, where the picolinic acid binds the zinc ion by N-pyridine 1 0 2 0 8.51 (0.02) and O-carboxylato atoms. Beside, the selected model of zinc 0 0 1 1 10.47 (0.03) with bioligand was found to consist of Zn(L), Zn(L)2 and Zn(L)3 0 0 1 2 19.27 (0.04) species. Ornithine 0 0 1 3 20.98 (0.05) Ternary complexes: In general, the overall formation 1 0 1 0 4.10 (0.04) constant can be written as follows (charges are omitted for 1 0 2 0 7.30 (0.07) simplicity): 0 0 1 1 9.68 (0.01) 0 0 1 2 17.72 (0.02) zn(l ) + )P(p + L(q ) + (r H) ↔ Zn( )l )P( p L( )q (H)r Cysteine 0 0 1 3 19.35 (0.06) 1 0 1 0 9.04 (0.03) zn[ l PpL qH r ] 1 0 2 0 17.54 (0.06) βlpqr = [][][][]Zn l P p L q H r 0 0 1 1 9.48 (0.01) 0 0 1 2 15.76 (0.01) Ternary complexes involving Zn(II)-picolinic acid- 0 0 1 3 17.92 (0.04) Histidine amino acids: The possible formation of ternary complexes 1 0 1 0 6.13 (0.08) via simultaneous mechanisms has been confirmed by compa- 1 0 2 0 12.09 (0.09) rison with con structed theoretical curves.
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