Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study

Fatou Faye,Aïssatou Alioune Gaye,Mohamed Gaye,Nathalie Gruber,Papa Samba Camara,Farba Bouyagui Tamboura,Amadou Guèye

doi:10.11648/j.ajac.20210901.12

Fatou Faye, Aïssatou Alioune Gaye + Show 5 more

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https://doi.org/10.11648/j.ajac.20210901.12

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Abstract

The compounds (E)–2–amino–N'–(1–(2–hydroxyphenyl)ethylidene)–2–oxoacetohydrazide (I) and (E)–N'–(2–hydroxy–3–methoxybenzylidene)–2–amino–2–oxoacetohydrazide (II) were synthetized by the 1:1 ratio condensation reaction of oxamic hydrazide and 2–hydroxyacetophenone or o–vanillin respectively. The two compounds were characterized by physico–chemical analyses, elemental analysis, FTIR, 1H and 13C NMR spectroscopies techniques. The structure of the compound (I) was determined by single–crystal X–ray diffraction study. The compound (I) (C10H11N3O3) crystallises in the triclinic space group P–1 with the following unit cell parameters: a = 7.0399 (5) Å, b = 8.6252 (8) Å, c = 9.5474 (9) Å, a = 81.730 (3)°, b = 72.738 (3)°, g = 67.450 (3)°, V = 510.99 (8) Å3, Z = 2, T = 173 (2) K, m = 0.11 mm–1, Dcalc = 1.438 g/cm3, Rint = 0.028, Rsigma = 0.073. The oxamic hydrazide moiety of the molecule is slightly twisted as reflected by the torsion angles values of 177.2 (2)° [N1–N2–C9–C10], –171.3 (3)° [N2–C9–C10–N3], –4.6 (4)° [O2–C9–N2–N1] and 8.4 (4)° [O3–C10–C9–N2]. The intramolecular hydrogen bond O1(phenol)–H1•••N1(hydrazide) which close in S (6) ring stabilized the conformation. The intermolecular hydrogen bonds, C3–H3•••O1i(phenol) (i: −x+1, −y, −z+1), N3(amide)–H3A•••O3ii(amide) (ii: −x+1, −y+2, −z) and N3(amide)–H3B•••O2iii(hydrazide) (iii: −x+1, −y+1, −z) lead to the formation of sheets parallel to ac plane. Compounds (I) and (II) showed antioxidant activities less than 10% inhibition of DPPH.

Highlights

Ditopic Schiff bases prepared from oxamic or thioxamic hydrazide have been widely reported in the literature by chemists and in particular those interested in coordination chemistry [1,2,3,4,5,6]
We report the spectroscopic study of the two compounds and the structure of (I) obtained by X–ray diffraction
In the synthesis of Schiff bases from oxamic hydrazide, the subject of our study, the use of these solvents leads to excessively long reaction times

Summary

Introduction

Ditopic Schiff bases prepared from oxamic or thioxamic hydrazide have been widely reported in the literature by chemists and in particular those interested in coordination chemistry [1,2,3,4,5,6]. A wide variety of heterocyclic molecules with good medicinal properties are obtained starting from these oxamic precursors [18]. Schiff's bases are synthesized from oxamic hydrazide and used for the preparation of complexes with transition metal and lanthanide ions [9, 22,23,24,25]. The properties of these complexes are evaluated in superoxide catalysis [2, 3] and magnetism [26]. It is in this perspective that we have studied these types of ligands and reported their

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