Abstract
A macrocyclic hydrazone Schiff bases were synthesized by reaction of pyridine-2,6-dicarbohydrazide and pyridine-2,6-thiodicarbohydrazide with dicarbonyls. Schiff bases have been characterized by melting point, elemental analyses, LC-MS, IR, 1 H and 13 C NMR spectral data. The Schiff base from pyridine-2,6-dicarbohydrazide and benzil has been studied by liquid–liquid extraction towards the d-metal ions (Cu(II) and Cr(III)) from aqueous phase to organic phase. The effect of chloroform and dichloromethane as organic solvents over the metal chlorides extraction was investigated at 25 ± 0.1°C by using flame atomic absorption.
Highlights
Hydrazones are special group of compounds in the Schiff bases family. They are characterized by the presence of (C=N-N=C). the presence of two inter-linked nitrogen atoms was separated from imines, oximes, etc. hydrazone Schiff bases of acyl, aroyl and heteroacroyl compounds have additional donor sites like C=O
In the context of the above applications we have reported here the synthesis and characterization of novel macrocyclic hydrazone Schiff bases
A Survey of the literature reveal that no work has been carried out on the synthesis of mcrocyclic hydrazone Schiff bases derived from pyridine-2,6-dicarbohydrazide and dicarbonyls
Summary
Schiff bases are widely studied and used in the fields of organic synthesis and metal ion complexation [1,2] for a number of reasons: their physiological and pharmacological activities [3,4,5] their use in ionselective electrodes [6,7,8,9,10,11] in the determination of heavy metals ions in environmental samples [12] and in the extraction of metals ions [13,14] and their many catalytic applications (e.g. for epoxidation of olefins, alkene cyclopropanation [15,16] trimethylsilylcyanation of ketones [17] asymmetric oxidation of methyl phenyl sulfide enantioselective epoxidation of silylenol [18] and ring-opening polymerization of lactide [19]). The additional donor sites make them more flexible and versatile This versatility has made hydrazones good polydentate chelating agents that can form a variety of complexes with various transition and inner transition metals and have attracted the attention of many researchers. A Survey of the literature reveal that no work has been carried out on the synthesis of mcrocyclic hydrazone Schiff bases derived from pyridine-2,6-dicarbohydrazide and dicarbonyls. These Schiff bases have donor sites with the NON sequence and varied coordination abilities. In the present study, we synthesized hydrazone Schiff base (V) and used it as an organic chelating agent to extract some metal cations from their aqueous to another organic phase. For the application to analysis, solvent extraction conditions such as solution pH, the types of organic solvents, the concentration of Schiff base and the effect of aqueous to organic phase
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