Bivalent transition metal complexes of ONO donor hydrazone ligand: Synthesis, structural characterization and antimicrobial activity

Bhaskar, Ravindra; Salunkhe, Nilesh; Yaul, A. R.; Aswar, A. S.

doi:10.1016/j.saa.2015.06.121

Cited by 52 publications

(27 citation statements)

References 27 publications

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“…ACCEPTED MANUSCRIPT 4 4 two tautomeric forms was determined for the solid substance, as well as for highly concentrated solutions, whereas only the hydrazone tautomer is present in diluted solutions [9,10]. It is anticipated that the formation of inter-and intra-molecular hydrogen bonds strongly influence these equilibria [11].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

Saeed

Arshad

Bolte

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The 2-(phenyl-hydrazono)-succinic acid dimethyl ester compound was synthesized by reacting phenylhydrazine with dimethylacetylene dicarboxylate at room temperature and characterized by elemental analysis, infrared, Raman, (1)H and (13)C NMR spectroscopies and mass spectrometry. Its solid state structure was determined by X-ray diffraction methods. The X-ray structure determination corroborates that the molecule is present in the crystal as the hydrazone tautomer, probably favored by a strong intramolecular N-H···O=C hydrogen bond occurring between the carbonyl (-C=O) and the hydrazone -C=N-NH- groups. A substantial fragment of the molecular skeleton is planar due to an extended π-bonding delocalization. The topological analysis of the electron densities (Atom in Molecule, AIM) allows characterization of intramolecular N-H···O interaction, that can be classified as a resonant assisted hydrogen bond (RAHB). Moreover, the Natural Bond Orbital population analysis confirms that a strong hyperconjugative lpO1→σ*(N2-H) remote interaction between the C2=O1 and N2-H groups takes place. Periodic system electron density and topological analysis have been applied to characterize the intermolecular interactions in the crystal. Weak intermolecular interactions determine the crystal packing, and the prevalence of non-directional dispersive contributions are inferred on topological grounds. The IR spectrum of the crystalline compound was investigated by means of density functional theory calculations carried out with periodic boundary conditions on the crystal, showing excellent agreement between theory and the experiments. The vibrational assignment is complemented with the analysis of the Raman spectrum.

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Section: Accepted Manuscriptmentioning

confidence: 99%

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

Saeed

Arshad

Bolte

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…The magnetic moment of this complex was 1.65 BM, which is corresponding to a low spin octahedral environment around the Ru(II) ion. Also iron(III) complex (14) demonstrated an octahedral geometry around the Fe(III) ion, this is supported by the presence of three bands at 465, 550, 580 nm assignable to 6 A 1g → 4 T 1g (G), 6 A 1g → 4 T 2g (G)and 6 A 1g → 4 Eg(G) transitions [66,73]. The magnetic moment recorded by this complex was 6.01 BM referring to a high spin octahedral geometry around the Fe(III) ions [66,73].…”

Section: Ru(iii) and Fe(iii) Complexesmentioning

confidence: 70%

“…They do not show d-d transitions, and the observed bands are only intra-ligand transitions. The zinc(II) complex (6) show band at 400 nm assignable to the ligand to metal charge transfer transitions (LMCT) [65].…”

Section: Zn(ii) Complexmentioning

confidence: 99%

“…Complexes (4), (8), (9), (13) and (14) were found to afford M 2 L formulae while complex (11) adopted ML 2 formulae. The ligand acted as a neutral (bidentate [11], tridentate [6,7], monobasic (tridentate [2,3,5,12]), dibasic (tridentate [10], tetradentate [4,8,9,13,14]) chelating to the metal ions via nitrogen atoms of aceto-amino and azomethine groups, carbonyl oxygen atom in its enolic or ketonic form and/or protonated or deprotonated oximino nitrogen atom, adopting an octahedral, tetrahedral or square planar geometry around metal ions. The antimicrobial activity of the ligand, as well as the metal complexes, was examined using Amphotericin B and Amoxicillin as drugstandards against Aspergillus niger (A.niger) and Escherichia coli (E. coli) ,respectively.…”

mentioning

confidence: 99%

“…. Hydrazone ligands represent a class of Schiff base with an extra function group characterized by a nitrogen-nitrogen covalent bond that enhances their capability to form more stable metal complexes via reaction with most of the transition metal ions [6,7]. Both hydrazide and hydrazone compounds have drawn much concern in order to investigate their structures as well as their enormous biomedical activities as: antioxidant [8,9], analgesic, anti-inflammatory [10], antimalarial, anti-leishmanial and anti-trypanosomal [11], anti-convulsant [(12)], antibacterial [13,14], antiplatelet [15], antitumor [16] and antiviral [17,18] activities.…”

mentioning

confidence: 99%

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Preparation, characterization and Microbicide activities of N'-((3-(hydroxyimino)butan-2-ylidene)-2-(phenylamino)acetohydrazide and its complexes

et al. 2017

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, UO 2 2+ and VO 3 -). The ligand, N'-((3-(hydroxyimino) butan-2-ylidene)-2-(phenylamino)acetohydrazide was prepared by refluxing an equimolar amount of phenyl amino acetohydrazide with 2,3-butanedione monoxime. The synthesized compounds were characterized using elemental and thermal analyses, NMR, IR, U.V spectroscopy, magnetic and conductance measurements. The results demonstrated that complexes (2), (3), (5-7), (10) and (12) were formed in 1L:1M molar ratio. Complexes (4), (8), (9), (13) and (14) were found to afford M 2 L formulae while complex (11) adopted ML 2 formulae. The ligand acted as a neutral (bidentate [11], tridentate [6,7], monobasic (tridentate [2,3,5,12]), dibasic (tridentate [10], tetradentate [4,8,9,13,14]) chelating to the metal ions via nitrogen atoms of aceto-amino and azomethine groups, carbonyl oxygen atom in its enolic or ketonic form and/or protonated or deprotonated oximino nitrogen atom, adopting an octahedral, tetrahedral or square planar geometry around metal ions. The antimicrobial activity of the ligand, as well as the metal complexes, was examined using Amphotericin B and Amoxicillin as drugstandards against Aspergillus niger (A.niger) and Escherichia coli (E. coli) ,respectively. The ligand demonstrates a high cytotoxicity against A.niger whereas it recorded a moderate activity against E. coli. It is interestingly found that zinc(II) complex (6), copper(II) complexes (8) and (10) recorded higher activities than the Amphotericin B drug with 122%, 116% and 111.1% percentages respectively against A.niger. Zinc(II) complex (6) was also the most sensitive complex against E. coli with (94.1 %) comparable to Amoxicillin.

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Characterization and thermal studies of nano‐synthesized Mn(II), Co(II), Ni(II) and Cu(II) complexes with adipohydrazone ligand as new promising antimicrobial and antitumor agents

Gaber

Khedr

Elsharkawy

2017

Applied Organom Chemis

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New seven complexes of N 1 ,N 6 -bis((2-hydroxynaphthalin-1-yl)methinyl)) adipohydrazone (H 2 L) with MnCl 2 •4H 2 O, CoCl 2 •6H 2 O, NiCl 2 •6H 2 O, CuCl 2 •2H 2 O, Cu(NO 3 ) 2 •3H 2 O, CuSO 4 •5H 2 O, and Cu(OAc) 2 •2H 2 O have beenprepared and characterized by the aid of elemental and thermal analyses, spectra (FT-IR, 1 H NMR, MS, UV-Vis, ESR, X-ray powder diffraction), molar conductance and magnetic moment measurements. The XRD results unambiguously confirmed the nano-sized particles of the complexes. The results showed that H 2 L behaves as dibasic tetra-dentate ligand towards the metal ions of interest. The low molar conductance values revealed the non-electrolytic nature for the chelates. The magnetic moment data, UV-Vis and ESR spectra denoted the formation of octahedral geometries for Mn(II) and Ni(II) complexes, whereas Co(II), Cu(II) complexes exhibited tetrahedral arrangement. The activation parameters for the thermal decomposition stages were calculated from TGA curves using Coats-Redfern and Horowitz-Metzger methods. The obtained data were confirmed by 3-D molecular modeling of the ligand and some complexes. The investigated compounds were screened for their antimicrobial activities against different types of organisms and antitumor activities towards human liver Carcinoma (HEPG2) cell to access their potential chemotherapeutic use. The free ligand (H 2 L) exhibited a weak inhibition of cell viability with IC 50 of 11.80 μg/ml, complexes 4, 6 and 7 showed a moderate activity with IC 50 of 5.56, 7.71 and 5.67 μg/ml, whereas complexes 1, 2, 3, and 5 displayed a strong anticancer activity with IC 50 of 4.65, 3.97, 3.30 and 4.84 μg/ml, compared with IC 50 value of 4.73 μg/ml for the doxorubicin (standard cytotoxin drug).

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Bivalent transition metal complexes of ONO donor hydrazone ligand: Synthesis, structural characterization and antimicrobial activity

Cited by 52 publications

References 27 publications

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

Preparation, characterization and Microbicide activities of N'-((3-(hydroxyimino)butan-2-ylidene)-2-(phenylamino)acetohydrazide and its complexes

Characterization and thermal studies of nano‐synthesized Mn(II), Co(II), Ni(II) and Cu(II) complexes with adipohydrazone ligand as new promising antimicrobial and antitumor agents

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