NDLI: Novel repaglinide complexes with manganese(II), iron(III), copper(II) and zinc(II): Spectroscopic, DFT characterization and electrochemical behaviour

Content Provider	Springer Nature Link
Author	Sadaoui Kacel, S. Zaater, S. Bensouilah, N. Djebbar, S.
Copyright Year	2016
Abstract	Novel transition metal complexes with the repaglinide ligand [2-ethoxy-4-[N-[1-(2piperidinophenyl)-3-methyl-1-1butyl] aminocarbonylmethyl]benzoic acid] (HL) are prepared from chloride salts of manganese(II), iron(III), copper(II), and zinc(II) ions in water-alcoholic media. The mononuclear and non-electrolyte [M(L)$_{2}$(H$_{2}$O)$_{2}$]•nH$_{2}$O (M = Mn$^{2+}$, n = 2, M = Cu$^{2+}$, n = 5 and M = Zn$^{2+}$, n = 1) and [M(L)$_{2}$(H$_{2}$O)(OH)]•H$_{2}$O (M = Fe$^{3+}$) complexes are obtained with the metal:ligand ratio of 1:2 and the L-deprotonated form of repaglinide. They are characterized using the elemental and molar conductance. The infrared, $^{1}$H and $^{13}$C NMR spectra show the coordination mode of the metal ions to the repaglinide ligand. Magnetic susceptibility measurements and electronic spectra confirm the octahedral geometry around the metal center. The experimental values of FT-IR, $^{1}$H, NMR, and electronic spectra are compared with theoretical data obtained by the density functional theory (DFT) using the B3LYP method with the LANL2DZ basis set. Analytical and spectral results suggest that the HL ligand is coordinated to the metal ions via two oxygen atoms of the ethoxy and carboxyl groups. The structural parameters of the optimized geometries of the ligand and the studied complexes are evaluated by theoretical calculations. The order of complexation energies for the obtained structures is as follows: $$Fe(III) complex < Cu(II) complex < Zn(II) complex < Mn(II) complex.$$ The redox behavior of repaglinide and metal complexes are studied by cyclic voltammetry revealing irreversible redox processes. The presence of repaglinide in the complexes shifts the reduction potentials of the metal ions towards more negative values.
Starting Page	1519
Ending Page	1530
Page Count	12
File Format	PDF
ISSN	00224766
Journal	Journal of Structural Chemistry
Volume Number	57
Issue Number	8
e-ISSN	15738779
Language	English
Publisher	Pleiades Publishing
Publisher Date	2017-01-22
Publisher Place	Moscow
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	metal complexes repaglinide ligand synthesis DFT electrochemical behavior Inorganic Chemistry Physical Chemistry Atomic, Molecular, Optical and Plasma Physics Atomic/Molecular Structure and Spectra Solid State Physics
Content Type	Text
Resource Type	Article
Subject	Materials Chemistry Physical and Theoretical Chemistry Inorganic Chemistry

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