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Spectrophotometric and conductometric studies of new synthesized azo derived from pyrazole as analytical reagents

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Abstract

A new pyrazole derivatives azo dye 1-(3-phenyl-5-Pyrazolylazo)-R acid (L1) and 5-(3-phenyl-5-Pyrazolylazo)-8-hydroxy quinoline (L2) was synthesized. The acid–base equilibrium, ionization constants, the effect of pH and some organic solvents on the spectra of ligands, the chromogenic reaction and the stability constant of Co+2, Cu+2,Ni+2 and Zn+2 ion complexes with ligands were studied and determined spectrophotometrically and conductometrically. The optimum pH was determined for the ligands and the complexes. 2:1 and 1:1 (L:M) stoichiometric complexes have been formed in solutions. The stability constants order of the under study complexes was Co+2 < Ni+2 < Cu+2. These metal ions were determined using the ligands as indicators. The reagents can be also useful to use as indicators in acid–base titrations as confirmed experimentally.

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References

  • Anastassova NO, Yancheva DY, Mavrova AT, Kondva-Burdina MS, Tzankova VI, Hristova-Avakumova NG, Hadjimitova VA (2018) Design, synthesis, antioxidant properties and mechanism of action of new N, N′-disubstituted benzimidazole-2-thione hydrazone derivatives. J Mole Struct 1165:162. https://doi.org/10.1016/j.molstruc.2018.03.119

    Article  CAS  Google Scholar 

  • Banerjee B, Nandi SK, Caudhuri SR (1983) Characterization of 3(5)-Aminopyrazole and its complexes with cobalt (II), Nickel (II), Copper(II), Zinc(II), Cadmium(II) and Mercury(II). Indian J Chem Sect A 22A(10):875

    CAS  Google Scholar 

  • Bayliss NS, Macrae EG (1950) The effect of the electrostatic polarization of the solvent on electronic absorption spectra in solution. J Chem Phys 18(3):292

    Article  CAS  Google Scholar 

  • Beck MT (1970) Chemistry of Complex Equilibria, Van Nostrand Reinhold Company Ltd, London 86

  • Britton HTS (1952) Hydrogen Ions, 4th. Chapman and Hall, London

    Google Scholar 

  • Busev AI, Akimov VK, Gusev SI (1965) Pyrazolone Derivatives as Analytical Reagents. Russ Chem Rev (eng Trans) 34:237

    Article  Google Scholar 

  • Can OD, Osmaniye D, Ozkay UD, Saglik BN, Levent S, Llgin S, Baysal M, Ozkay Y (2017) MAO enzymes inhibitory activity of new benzimidazole derivatives including hydrazone and propargyl side chains. Euro J Med Chem 131:92–106. https://doi.org/10.1016/j.ejmech.2017.03.009

    Article  CAS  Google Scholar 

  • Cotton FA, Wilkinson CW (1967) Advanced Inorganic Chemistry. Inter Science, New York, p 92

    Google Scholar 

  • Elguero J (1982) Comprehensive Heterocyclic Chemistry II, 3: 70

  • Elnagdi MH, El-moghayer MRH, Fleita DH, Hafez EAA, Fahmy SM (1976) Pyrimidine derivatives and related compounds. 4. A route for the synthesis of pyrazolo [3,4-e]-as-triazines, pyrazolo[3,4-d]pyrimidines, and pyrazolo[1,5-c]-as-triazines. J Org Chem 41(24):3781

    Article  CAS  Google Scholar 

  • Evans NA, Waters PJ (1978) 2-Pyrazoline dyes for wool and nylon. J Soc Dyers Colourists 94(6):252

    Article  CAS  Google Scholar 

  • Gati L, Szalay L (1950) Acta Phys Chem 5:87

    Google Scholar 

  • Jacimovic Z, Tomic DZ, Bogdanović GA (1999) Transition metal complexes with pyrazole-derived ligands X. [Zn(CH3COO)2L2]. 2meoh (L = 3-Amino-5-Phenylpyrazole). Acta Crystallogr Sect C Cryst Struct Commun 55(11):1769

    Article  Google Scholar 

  • Job P (1928) Formation and stability of inorganic complexes in solution. Ann Chim 9:113–203

    CAS  Google Scholar 

  • Joshi KC, Pothak VN, Grag MU (1979) Synthesis of some new fluorine-containing 5-amino-1,3-disubstituted pyrazoles and 1H-pyrazolo[3,4-b]pyridines. J Heterocycl Chem 16(6):1141

    Article  CAS  Google Scholar 

  • Kamlet MJ, Talf RW (1976) The solvatochromic comparison method 1. The beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc 98(2):377. https://doi.org/10.1021/ja00418a009

    Article  CAS  Google Scholar 

  • Karrouchi K, Radi S, Ramli Y, Taoufik J, Mabkhot YN, Al-aizari FA, Ansar M (2018) Synthesis and pharmacological activities of pyrazole derivatives: a review. Molecules 23:134. https://doi.org/10.3390/molecules23010134

    Article  CAS  PubMed Central  Google Scholar 

  • Kater MM, Issa YM, Shoulry AF, El-seify FAA (1979) Spectrophotometric studies on complexes of Co(II), Ni(II) and Cu(II) with benzimidazolylazo derivatives, Mikrochim. Acta II 72(5–6):501

    Google Scholar 

  • Katritzky A, Rees CW (1984) Comprehensive Heterocyclic Chemistry. Pergaman Press, Oxford, p 298

    Google Scholar 

  • Kosower EM (1956) The effect of solvent on charge-transfer complex spectra. J Am Chem Soc 78(21):5700

    Article  CAS  Google Scholar 

  • Mitra A, Banerjee T, Roychowdhury P, Chaudhuri S, Bera P (1997) Synthesis and spectroscopic characterisation of cobalt(III) complexes with S-benzyl dithiocarbazate of 5-methyl-3-formyl pyrazole (HMPzSB): X-ray crystal structure of [Co(MPzSB)2]Cl. Polyhedron 16(21):3735. https://doi.org/10.1016/S0277-5387(97)00151-4

    Article  CAS  Google Scholar 

  • Mohamed AA (2001) Thermodynamic study of the complexation processes between 2,4-diamino-3,5-dicyano thiophene and Cu2+, Ni2+, Zn2+, Co2+ and Mn2+ in 20% n-propanol-water solvent. Al-Azhar Bull Sci 12(2):65

    Google Scholar 

  • Nakum KJ, Patel JR, Gupta VK, Jadeja RN (2019) Crystal Structure of 5-Butoxy-4-((3-butoxyphenyl)diazenyl)-3-methyl-1-phenyl-1H-pyrazole. Crystallogr Reports 64:1051–1054

    Article  CAS  Google Scholar 

  • Omar MM (2002) Spectroscopic spectrophotometric and potentiometric studies on 3-(naphthylazo)-5-phenylpyrazole dye and its metal chelates. Anal Chim 92(5–6):601

    CAS  Google Scholar 

  • Omar MM, El-seify FAA (1991) Metal chelates of benzimidazolylazo derivatives. Monatshefte Fur Chemie 122(6–7):445

    Article  CAS  Google Scholar 

  • Omar MM, El-Seify FAA, Issa YM (1993) Potentiometric and Spectrophotometric Studies of some Benzimidazole Azo Dyes. Egypt J Chem 36(3):235

    CAS  Google Scholar 

  • Reichard C, Erlyon T (1988) Solvents and solvent effect in organic chemistry, 2nd Ed, Weinheim, Germany

  • Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94(8):2319. https://doi.org/10.1021/cr00032a005

    Article  CAS  Google Scholar 

  • Sandell EB (1959) Colorimetric Determination of Metals C. W. third Ed., Interscience, New York.

  • Suppan P (1968) Solvent effects on the energy of electronic transitions: experimental observations and applications to structural problems of excited molecules. J Chem Soc A (2):3125

  • Taft RW, Kamalet MJ (1976) The solvatochromic comparison method 2 The beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc 98(10):2886. https://doi.org/10.1021/ja00426a036

    Article  CAS  Google Scholar 

  • Ta-kamoto S, Fwenado Q, Ereiser H (1965) Structure and behavior of organic analytical reagents some Aryl Azo 8-Quinolinols. Anal Chem 37(10):1249

    Article  CAS  Google Scholar 

  • Takeda Y (1983) Thermodynamic study for dibenzo-24-crown-8 complexes with alkali metal ions in nonaqueous solvents. Bull Chem Soc Jpn 56:3600–3602. https://doi.org/10.1246/bcsj.56.3600

    Article  CAS  Google Scholar 

  • Vogel AI (1956) ‘Practical Organic Chemistry Including Quantitative Organic Analysis, 3ed. Longmans, London, p 854

    Google Scholar 

  • Welcher FJ (1965) The analytical uses of ethylene diamine tetra acetic acid. Van Nostrand, Princeton

    Google Scholar 

  • Yoe JH, Jones AL (1944) Colorimetric determination of iron with disodium-1,2-dihydroxybenzene-3,5-disulfonate. Ind Eng Chem Anal Ed 16(2):111

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Faculty of Engineering, Port Said University, Port Said, Egypt

    F. A. El-Seify

  2. Chemistry Department, Faculty of Science, Port Said University, Port Said, Egypt

    F. I. El-Dossoki & Mahmoud M. Gouda

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  1. F. A. El-Seify
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  2. F. I. El-Dossoki
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  3. Mahmoud M. Gouda
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Correspondence to F. I. El-Dossoki.

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El-Seify, F.A., El-Dossoki, F.I. & Gouda, M.M. Spectrophotometric and conductometric studies of new synthesized azo derived from pyrazole as analytical reagents. Chem. Pap. 75, 5917–5927 (2021). https://doi.org/10.1007/s11696-021-01753-1

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