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New nitrogen-donor pyrazole ligands for excellent liquid–liquid extraction of Fe2+ ions from aqueous solution, with theoretical study

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Abstract

New N-donor pyrazole derivatives L 1 –L 6 were prepared by monoalkylation, by simple and easy condensation of one equivalent of 1-(hydroxymethyl)-3,5-dimethylpyrazole and one equivalent of an appropriate primary amine. The compounds were used to extract different metal ions. Their capacity in extraction of Cu2+, Cd2+, Pb2+, Co2+, Ni2+, Zn2+, and Fe2+ was determined by measurement, by atomic absorption, of percentage extraction of the cation at pH 7. All the ligands tested extract these metals with different efficiency: efficiency of L 2 was 99 % for Fe2+ and 29 % for Zn; efficiency of L 4 was 24 % for Cu2+ and Cd2+ and 19 % for Pb2+. The geometries were optimized, the energies, spatial distributions, energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), the difference between these (E LUMO − E HOMO), known as energy band gap (ΔE), bond lengths, charges on the atoms, and electrostatic potential were then calculated. The molecule with smallest value of ΔE is the most reactive (least stable) and correlation proves that the efficiency of extraction of Fe2+ increases as molecular stability decreases.

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Acknowledgments

Financial support by la Commission Universitaire pour le Développement (CUD—Belgium) is highly appreciated. We thank also le Centre de l’Oriental des Sciences et Technologies de l’Eau (COSTE) for use of Atomic Absorption Spectroscopy.

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Authors and Affiliations

  1. LCAE-URAC18 COSTE, Faculté des Sciences Oujda & Faculté Pluridisciplinaire de Nador, Université Mohammed Premier, BP: 300, 62700, Selouane, Nador, Morocco

    Mohamed Khoutoul, Farid Abrigach, Abdelkader Zarrouk, Nour-Eddine Benchat, Morad Lamsayah & Rachid Touzani

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  1. Mohamed Khoutoul
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  2. Farid Abrigach
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  3. Abdelkader Zarrouk
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  6. Rachid Touzani
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Correspondence to Rachid Touzani.

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Khoutoul, M., Abrigach, F., Zarrouk, A. et al. New nitrogen-donor pyrazole ligands for excellent liquid–liquid extraction of Fe2+ ions from aqueous solution, with theoretical study. Res Chem Intermed 41, 3319–3334 (2015). https://doi.org/10.1007/s11164-013-1435-2

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