Structure of 2-(((1-(3-Bromophenyl)ethylidene)hydrazono)methyl)phenol and Its Application to the Spectrophotometric Determination of Iron(III)

Abstract

A novel reagent derived from salicylaldehyde has been synthesized and characterized by determining its crystalline structure through X-ray diffraction analysis. The complex formation of this reagent with iron(III) has been investigated by spectrophotometric methods. The dissociation constant of the reagent was determined by potentiometry in an aqueous–ethanolic medium, yielding pK = 9.66 ± 0.02. The interaction of iron(III) with 2-(((1-(3-bromophenyl)ethylidene)hydrazono)methyl)phenol in the presence and absence of diantipyrylmethane (DAM), diantipyrylphenylmethane (DAPhM), and diantipyrylpropylmethane (DAPrM) has been thoroughly studied. Optimal conditions for complex formation (λ_opt, pH_opt) were found. Iron(III) forms colored mixed-ligand complexes with the reagent in the presence of the third component—DAM, DAPhM, or DAPrM,—resulting in a hypsochromic shift in the absorption spectrum. The maximum yield of complexes was achieved in a more acidic medium compared to the binary complex. Molar absorption coefficients of the complexes and the ranges of compliance with Beer’s law were determined. Component ratios in the homogeneous and mixed-ligand complexes were established using isomolar series methods, as well as the relative yield of the Starik–Barbanel and equilibrium shift methods. These analyses revealed that the component ratio of Fe(III)–R in the binary complex is 1 : 2, while in the mixed-ligand complexes Fe(III)–R–DAM, Fe(III)–R–DAPhM, and Fe(III)–R–DAPrM, the ratios are 1 : 2 : 1, 1 : 1 : 1, and 1 : 1 : 2, respectively. The mixed-ligand complexes of iron(III) with 2-(((1-(3-bromophenyl)ethylidene)hydrazono)methyl)phenol exhibit favorable chemical-analytical characteristics. The developed procedure was successfully applied to the determination of trace amounts of iron(III) in oil sludge.