Synthesis, characterization, nano-sized binuclear nickel complexes, DFT calculations and antibacterial evaluation of new macrocyclic Schiff base compounds

Parsaee, Zohreh; Mohammadi, Khosro

doi:10.1016/j.molstruc.2017.02.026

Cited by 47 publications

(47 citation statements)

References 40 publications

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“…The stretching vibration of the phenolic ν(C-O) observed at regions 1232-1237 cm -1 in the free ligands undergo a hypochromic shift to 1311-1340 cm -1 Also, the appearance of new bands in the range of 839-850 cm regions in the complexes upon complexation as recorded in table 2. This shifts further confirms the coordination of the phenolic oxygen leading to the formation of C-O-M bond [4,14,19] (where M = Co, Mn and Mg). …”

Section: Fourier Transform Infrared Spectroscopy (Ft-ir)supporting

confidence: 61%

“…The compound was stable up to 260 °C and its decomposition started at 272 °C and finally completed at 340 °C, with the temperature of the highest decomposition observed at about 316 °C ( fig. 2) [4,12].…”

Section: -N'-{(e)-[4-(diethylamino)-2-hydroxyphenyl] Methylidene}-4-nmentioning

confidence: 99%

“…Mg(acac)(L 2 ) weight loss started at about 85 °C revealing four endothermal peaks corresponding to the removal of methoxylation, diethylamino, acetylacetonate and Schiff ligand molecule, the remaining mass seems likely to correspond to MgO as a residue ( fig. 4) [4,10]. However, the number of decomposition processes (stages) gives an indication of the degree of purity synthesised Schiff base ligands and their corresponding metal complexes [12,20].…”

Section: Fig 1: Tg/dtg Curves For Schiff Base Hl 1 : N'-{(e)-[4-(dimentioning

confidence: 99%

“…The 13 The C spectrum reveals the presence of ketonic carbon at δ 189.01 ppm, the signal of δ 161.4 ppm is due to the phenolic carbon, amide carbon at δ 161.2 ppm, δ 152.2 ppm (C=N) is due to carbon atom in the azomethine groups, aromatic carbons at δ 150.3, 149.6, 140.0, 131.1, 129.5, 129.1, 123.3, 121.7, 112.3 ppm, methylene carbon at δ 26.0 ppm, methyl carbon at δ 13.2 ppm [4,14,17,21]. 1 H NMR spectrum of the complex: Mg(acac)(L 1 ) exhibited singlet signals at δ 11.36 ppm which could be attributed to the proton of an amide nitrogen, azomethine proton signal at δ 8.44 ppm (1H, s), aromatic protons at 8.36 (1H, s), δ 8.35 (1H, s), δ 8.17 (1H, s), δ 8.15 (1H, s), signals appearing as multiplets in the δ 6.13-7.23 ppm region are due to the aromatic protons, methylene protons at the range δ 2.51-3.35 (multiplets), methyl protons at δ 2.14 (3H, d), δ 1.72 (3H, t), δ 1.11 (3H, t) ppm.…”

Section: : N'-{(e)-[4-(diethylamino)-2-hydroxyphenyl] Methylidene}-4-mentioning

confidence: 99%

“…Schiff base ligands bearing azomethine (>C=N-) functional group, possessing N, O, and S-donor atoms have been established as versatile pharmacophores for design and development of various biologically active compounds [3]. They are used in wide variety of applications such as anti-cancer, anti-corrosion, anti-HIV, anti-radical, anti-bacterial and anti-fungal material and DNA cleavage [2,4]. Some biologically important Schiff base derivatives include the imidazoles, pyrimidines, hydrazides and hydrazine's [5][6].…”

Section: Introductionmentioning

confidence: 99%

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Hydrazide Schiff Bases of Acetylacetonate Metal Complexes: Synthesis, Spectroscopic and Biological Studies

Dikio

Ejidike

Mtunzi

et al. 2017

Int J Pharm Pharm Sci

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Objective: The study was focused on the synthesis and spectroscopic studies of metal acetylacetonates and their complexes using bidentate Schiffbase ligands (NO), evaluation of their in vitro antibacterial potentials against pathogenic microorganism.Methods: Acetylacetonate salts of Cobalt (II), Manganese (II) and Magnesium (II) were prepared by reacting their metal hydroxides with acetylacetone. The metal complexes ofResults: The FT-IR spectra revealed that the Schiff bases acts as bidentate chelating ligand via a nitrogen of the azomethine and phenolic oxygen atoms. NMR reveals the presence of azomethine (HC=N) and aromatic hydrogens at expected chemical shifts confirming the formation of the Schiff base ligands. Thermal decomposition behaviour was studied by thermogravimetry revealing stability up to 260 °C. The compounds were evaluated for antibacterial potentials against Staphylococcus aureus and Enterococcus faecalis.

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Section: Fourier Transform Infrared Spectroscopy (Ft-ir)supporting

confidence: 61%

Section: -N'-{(e)-[4-(diethylamino)-2-hydroxyphenyl] Methylidene}-4-nmentioning

confidence: 99%

Section: Fig 1: Tg/dtg Curves For Schiff Base Hl 1 : N'-{(e)-[4-(dimentioning

confidence: 99%

Section: : N'-{(e)-[4-(diethylamino)-2-hydroxyphenyl] Methylidene}-4-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Hydrazide Schiff Bases of Acetylacetonate Metal Complexes: Synthesis, Spectroscopic and Biological Studies

Dikio

Ejidike

Mtunzi

et al. 2017

Int J Pharm Pharm Sci

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Synthesis, structural features and biochemical activity assessment of N,N′‐bis‐(2‐mercaptophenylimine)‐2,5‐thiophenedicarboxaldehyde Schiff base and its Co(II), Ni(II), Cu(II) and Zn(II) complexes

Aziz

Seda

2017

Applied Organom Chemis

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The tetradentate Schiff base ligand (SB), N,N′-bis-(2-mercaptophenylimine)-2,5thiophenedicarboxaldehyde was prepared via condensation of 2,5-thiophenedicarboxaldehyde with 2-aminothiophenol in a 1:2 molar ratio by conventional method. Additionally, its Co(II), Ni(II), Cu(II) and Zn(II) complexes have been synthesized and fully characterized by elemental analysis, FT-IR, 1 H NMR, 13 C NMR, UV-Vis, ESR, ESI-mass, conductivity and magnetic susceptibility measurements. Spectral studies suggested that, the Schiff base coordinate metal ions through the azomethine N-and deprotonated thiol S-atoms. Based on UV-Vis absorption and magnetic susceptibility data, tetrahedral geometry was assigned for both Co(II) and Zn(II) complexes, whereas on the other hand, square planar geometry for both Ni(II) and Cu(II) complexes. The Schiff base and its metal complexes were screened for their in vitro antimicrobial activity by minimum inhibitory concentration (MIC) method. Free radical scavenging activity of the novel compounds was determined by elimination of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals. In addition, the interactions of the free ligand and its complexes with calf thymus DNA (CT-DNA) were explored using absorption, emission and viscosity measurements techniques.

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Metal complexes of novel Schiff base derived from iron sandwiched organometallic and 4‐nitro‐1,2‐phenylenediamine: Synthesis, characterization, DFT studies, antimicrobial activities and molecular docking

Mahmoud

Deghadi

2018

Applied Organom Chemis

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The condensation of 2-acetylferrocene with 4-nitro-1,2-phenylenediamine in a 1:1 molar ratio, resulting in formation of a novel bi-dentate organometallic Schiff base ligand (L), (2-(1-((2-amino-5-nitrophenyl)imino)ethyl)cyclopenta-2,4-dien-1-yl)(cyclopenta-2,4-dien-1-yl)iron. Also, its Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes have been synthesized. The stoichiometric ratios of the prepared compounds were estimated using elemental analysis (C, H, N, M), molar conductivity, FT-IR, UV-Vis, 1 H-NMR, SEM and mass spectral analysis. Furthermore, their TG and DTG properties were studied. The geometrical structure of the complexes was found to be octahedral. From spectral analysis, the Schiff base coordinated to metal ions through the azomethine and amine groups. DFT-based molecular orbital energy calculations of the synthesized ligand have been studied, in which the ligand was theoretically optimized.The Schiff base and its metal complexes have been screened for their antimicrobial activities against different bacterial and fungal species by using disc diffusion method. The anticancer activities of the ligand and its metal complexes have also been studied towards breast cancer (MCF-7) and human normal melanocytes (HFB-4) cell lines. Molecular docking was also used to identify the interaction between the Schiff base ligand and its Cd(II) complex with the active site of the receptors of breast cancer mutant oxidoreductase (PDB ID: 3HB5), crystal structure of Staphylococcus aureus (PDB ID: 3Q8U) and yeast-specific serine/threonine protein phosphatase (PPZ1) of Candida albicans (PDB ID:5JPE).

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Synthesis, characterization, nano-sized binuclear nickel complexes, DFT calculations and antibacterial evaluation of new macrocyclic Schiff base compounds

Cited by 47 publications

References 40 publications

Hydrazide Schiff Bases of Acetylacetonate Metal Complexes: Synthesis, Spectroscopic and Biological Studies

Hydrazide Schiff Bases of Acetylacetonate Metal Complexes: Synthesis, Spectroscopic and Biological Studies

Synthesis, structural features and biochemical activity assessment of N,N′‐bis‐(2‐mercaptophenylimine)‐2,5‐thiophenedicarboxaldehyde Schiff base and its Co(II), Ni(II), Cu(II) and Zn(II) complexes

Metal complexes of novel Schiff base derived from iron sandwiched organometallic and 4‐nitro‐1,2‐phenylenediamine: Synthesis, characterization, DFT studies, antimicrobial activities and molecular docking

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