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

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, 1 H-NMR and 13 C-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 (DG 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 (pK A ) and distribution (Log K d ) constants in 1 M chloride medium and the acidity constants in aqueous medium (pK a ) 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.

Characterization, DFT, and antimicrobial evaluation of some new N2O2 tetradentate Schiff base metal complexes

“…Schiff bases were a broad class synthesized compounds, have a functional group -C=Ncalled azomethine or imine group, and were prepared from the reaction of the carbonyl group of ketone or aldehyde with a primary amine in acidic or basic media as a catalyst; the reaction was nucleophilic addition reaction through the carbonyl group (C=O). [1][2][3][4][5] The chemistry of Schiff base metal complexes containing oxygen and nitrogen as donor atoms were continued to attract the attention of researchers because they can be formed stable coordination compounds with most metals. [6][7][8][9] The Schiff bases and its complexes used in various fields such as catalysis, analytical chemistry, magnetic, and photoluminescence materials also exhibited significant biological properties.…”

Performance of Schiff Bases Metal Complexes and their Ligand in Biological Activity: A Review

“…The nucleophile is the primary amine which is reacts with the aliphatic or aromatic aldehyde or ketone to give an intermediate compound called carbinolamine. This intermediate compound was loses water molecule by hydrolyses process with acidic or basic media as a catalyst [5].…”

Synthesis and photophysical study of divalent complexes of chelating Schiff base

“…6 The industrial field of the Schiff base is used as corrosion inhibitors. 7,8 Recent studies focus on the preparation of new transition metal complexes of 1,2,4-triazole Schiff bases with their biological activity. Schiff bases complexes of triazole exhibit better biological activity than the free triazole derivatives and the geometry of these complexes suggested by different spectral analysis.…”