Synthesis, characterization, mass spectral fragmentation, thermal study and biological evaluation of new Schiff base ligand and its metal(II) complexes derived from 4-(diethylamino)salicylaldehyde and thiazole moiety

Yernale, Nagesh Gunvanthrao; Udayagiri, Mahadev Dhanraj; Mruthyunjayaswam, Bennikallu Hire Mathada

doi:10.5155/eurjchem.7.1.56-65.1372

Cited by 12 publications

(2 citation statements)

References 32 publications

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“…In the third stage of degradation, mass loss of the non-coordinated part of the ligand is observed at 62.08% (Calc. 62.04%) at ~450 °C and finally, the TG curve attains a horizontal level corresponding to the formation of stable metal oxide (½Cr2O3) [29,30].…”

Section: Thermogravimetric Analysismentioning

confidence: 99%

A heterocyclic N'-(4-(diethylamino)-2-hydroxybenzylidene)-4-oxopiperidine-1-carbohydrazide Schiff base ligand and its metal complexes: Synthesis, structural characterization, thermal behavior, fluorescence properties, and biological activities

Dongare

Aswar

2022

Eur J Chem

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A new heterocyclic hydrazone Schiff base ligand, N'-(4-(diethylamino)-2-hydroxy benzylidene)-4-oxopiperidine-1-carbohydrazide, (H2L) was derived by a condensation reaction of 4-oxopiperidine-1-carbohydrazide with 4-(diethylamino)-2-hydroxybenz-aldehyde. The ligand reacts with chloride salts of chromium(III), manganese(II), iron(III), cobalt(II), nickel(II), copper(II) and zinc(II) to form metal complexes of [Cr(L)(Cl)(H2O)2], [Mn(HL)(Cl)(H2O)2], [Fe(L)(Cl)(H2O)2], [Co(HL)(Cl)(H2O)2], [Ni(HL)(Cl)(H2O)2], [Cu(HL)(Cl) (H2O)2], [Zn(L)(H2O)], respectively. The structure of the hydrazone ligand was confirmed by elemental analysis and spectroscopic techniques, viz., FT-IR, 1H NMR, 13C NMR, and LC-MS spectroscopy. The newly synthesized ligand behaves as a tridentate ONO donor towards Cr, Mn, Fe, Co, Ni, Cu, and Zn metal ions. The spectral, magnetic moment, and thermal data indicate the octahedral geometry for all metal complexes except for Zn, which has tetrahedral geometry with 1:1 stoichiometry (M:L). ESR study revealed that π-bonding covalency is much stronger than the σ-bonding with axial distortion in the structure. The molar conductivity data suggested the nonelectrolytic nature of the complexes. The powder X-ray diffraction patterns suggest the nanocrystalline nature of the compounds. The SEM micrograph of the ligand significantly differs from its Ni(II) complex indicating coordination of Ni(II) ion to the ligand. The intense fluorescence emitted in the region of λExcitation 521 to 524 nm due to the functional fluorophores of the ligand and its manganese (II), chromium(III), cobalt(II), and zinc(II) complexes. Various kinetic parameters such as Ea, ∆S, ∆H, and ∆G of various decomposition steps were calculated from TGA diagrams using Coats-Redfern method and the thermal stability order was found to be Cr < Fe < Co < Mn = Cu < Zn < Ni. The antibacterial and antifungal activities of the ligand and its divalent and trivalent metal complexes were performed against the various pathogens viz. Escherichia coli, Salmonella typhi, Staphylococcus aureus, Bacillus subtilis, Candida albicans, and Aspergillus niger with reference to standard antibiotics viz. ofloxacin, azithromycin, and fluconazole. All metal complexes showed promising biological activity as compared with their parent ligand and may be used as a potential antimicrobial candidate in biological science.

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Section: Thermogravimetric Analysismentioning

confidence: 99%

A heterocyclic N'-(4-(diethylamino)-2-hydroxybenzylidene)-4-oxopiperidine-1-carbohydrazide Schiff base ligand and its metal complexes: Synthesis, structural characterization, thermal behavior, fluorescence properties, and biological activities

Dongare

Aswar

2022

Eur J Chem

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“…The precipitate was filtered, washed with ethanol and left to dry in air. The product was recrystallized from ethanol [13,14].…”

Section: Synthesis Of the Ligand (Hl)mentioning

confidence: 99%

Synthesis, characterization and biological activity of a Schiff base derived from o-amino benzoic acid and its Co(II), Cd(II) and Ni(II) complexes

et al. 2020

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Equimolar amounts of imidazoleacetophenone and 2-aminobenzoic acid were combined together and the Schiff base 4(1H-imidazole-yl)acetophenoneanthranilic acid was prepared as a new bidentate complexing agent. The synthesized ligand was reacted with cobalt(II), cadmium(II), and nickel(II) ions yielding air stable complexes. For quantification and characterization purposes, elemental analysis, infrared spectra, electronic spectra, proton nuclear magnetic resonance spectra and mass spectra studies were carried out on the obtained complexes and ligand. Thermogravimetric analysis and magnetic susceptibility measurements were also used for characterization. The ligand IR spectrum showed that the ligand acts as a bidentate coordinates to the metal ions through the nitrogen and oxygen atoms.Measurements of magnetic susceptibility for Ni(II) and Co(II) complexes were found to be 3.4 and 3.8 B.M., respectively, in the range normal for the octahedral geometry. The conductivity measurements revealed that the chelates are non-electrolytes. An in vitro antimicrobial investigation was also carried out for the free ligand and its metal complexes against a number of bacterial and fungal strains, to assess their antimicrobial properties by diffusion technique. Antimicrobial activity of the prepared complexes showed higher activity than the free ligand.

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Biological aspects of Schiff base–metal complexes derived from benzaldehydes: an overview

Mohapatra¹,

Das

Pradhan³

et al. 2018

J IRAN CHEM SOC

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Synthesis, characterization, mass spectral fragmentation, thermal study and biological evaluation of new Schiff base ligand and its metal(II) complexes derived from 4-(diethylamino)salicylaldehyde and thiazole moiety

Cited by 12 publications

References 32 publications

A heterocyclic N'-(4-(diethylamino)-2-hydroxybenzylidene)-4-oxopiperidine-1-carbohydrazide Schiff base ligand and its metal complexes: Synthesis, structural characterization, thermal behavior, fluorescence properties, and biological activities

A heterocyclic N'-(4-(diethylamino)-2-hydroxybenzylidene)-4-oxopiperidine-1-carbohydrazide Schiff base ligand and its metal complexes: Synthesis, structural characterization, thermal behavior, fluorescence properties, and biological activities

Synthesis, characterization and biological activity of a Schiff base derived from o-amino benzoic acid and its Co(II), Cd(II) and Ni(II) complexes

Biological aspects of Schiff base–metal complexes derived from benzaldehydes: an overview

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