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Synthesis and Characterization of a Novel Series of Amphiphilic Mercapto-1,2,4-Triazole Schiff Base Ligands: Investigation of their Behavior in Hydro-Organic Solutions

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Journal of Surfactants and Detergents

Abstract

A novel series of four Schiff base amphiphiles derived from 3-mercapto-1,2,4-triazole and different alkyl chains were successfully prepared by a new synthetic three-step method. The chemical structures of the different ligands were characterized by elemental analysis, FT-IR spectroscopy, 1H-NMR and 13C-NMR spectra. The effect of the chain length on the solution behavior of the amphiphilic ligands were studied, in both homogeneous and heterogeneous systems, using pH-metric and spectrophotometric methods. Based on the electronic spectroscopy data, some parameters governing their surfactant properties, such as the critical micelle concentration (CMC), the micellization free energy (ΔG mic) and the hydrophilic-lipophilic balance (HLB) were evaluated in chloroform and discussed. The behavior of the four Schiff bases in the heterogeneous chloroform-water mixture was then explored through the establishment of their acidity (pKA) and distribution (Log K d) constants in 1 M chloride medium and the acidity constants in aqueous medium (pKa) were deduced. Results showed that an increase of the alkyl chain decreases the distribution of the ligands and increases their acidity. The extractive performance of the Schiff base amphiphiles were investigated towards Ni(II) from a chloride medium at 30 °C. The analysis of extraction data revealed that the synthesized Schiff bases exhibit a better and faster extractability than many ligands reported in the literature.

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  1. Laboratory of Chemistry and Electrochemistry of Metallic Complexes (LCECM), Department of Industrial Organic Chemistry, Faculty of Chemistry, University of the Sciences and Technology of Oran-Mohamed Boudiaf USTOMB, BP-1505, EL-M’naouer, Oran, Algeria

    Nadia Boceiri, Tayeb Benabdallah, Mohammed Hadj Youcef & Hasnia Reffas

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  1. Nadia Boceiri
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  2. Tayeb Benabdallah
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Boceiri, N., Benabdallah, T., Hadj Youcef, M. et al. Synthesis and Characterization of a Novel Series of Amphiphilic Mercapto-1,2,4-Triazole Schiff Base Ligands: Investigation of their Behavior in Hydro-Organic Solutions. J Surfact Deterg 19, 583–597 (2016). https://doi.org/10.1007/s11743-016-1811-1

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