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Hydrolysis and Extraction Properties of Aroylhydrazones Derived from Nicotinic Acid Hydrazide

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Abstract

The kinetics of hydrolysis of N′-salicylidene-3-pyridinecarbohydrazide (1) and N′-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide (2) were investigated in the dioxane/water (1/1, volume ratio) solvent system in acidic and basic media, and the corresponding reaction mechanisms were proposed. The kinetic results suggest that in the acidic solutions the rate-determining step of the hydrolysis reaction is the attack of a water molecule on the protonated azomethine group, whereas in the basic medium it is the attack of water on the completely deprotonated hydrazone. By analyzing the temperature dependence of the reaction rates, the thermodynamic activation parameters, i.e. activation enthalpy and entropy, were also evaluated and discussed. The complexation reactions of vanadium(V) with aroylhydrazones 1 and 2 as well as the extraction of V(V) from aqueous to an organic phase were studied spectrophotometrically. The optimum conditions for complex formation and extraction of vanadium(V) into chloroform solutions of compounds 1 or 2 have been evaluated. Based on the results obtained by Job’s method and the equilibrium shift method, the stoichiometries of the complexes were determined to be 1:1. The effect of foreign ions on V(V) extraction by compound 2 has been determined as well.

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Acknowledgments

This work was supported by the Ministry of Science, Education and Sports of the Republic of Croatia (projects 119-1191342-2959, 119-1191342-2960, 119-1191342-1083, and 006-0061247-0009).

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Authors and Affiliations

  1. Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, 10000, Zagreb, Croatia

    A. Budimir

  2. Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000, Zagreb, Croatia

    T. Benković, V. Tomišić, A. Gojmerac Ivšić & N. Galić

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  1. A. Budimir
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  2. T. Benković
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  3. V. Tomišić
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  4. A. Gojmerac Ivšić
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  5. N. Galić
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Correspondence to N. Galić.

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Budimir, A., Benković, T., Tomišić, V. et al. Hydrolysis and Extraction Properties of Aroylhydrazones Derived from Nicotinic Acid Hydrazide. J Solution Chem 42, 1935–1948 (2013). https://doi.org/10.1007/s10953-013-0081-z

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  • DOI: https://doi.org/10.1007/s10953-013-0081-z

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