Cis-dioxidomolybdenum(VI) complexes with chiral tetradentate Schiff bases: Synthesis, spectroscopic characterization and catalytic activity in sulfoxidation and epoxidation

Karman, Marta; Romanowski, Grzegorz

doi:10.1016/j.ica.2020.119832

Cited by 16 publications

(10 citation statements)

References 47 publications

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“…The principal interest in the chemistry of molybdenum(VI) complexes with Schiff-base ligands arises from their biological and pharmacological importance [ 1 , 2 ]. To a greater extent, molybdenum compounds have been widely applied and researched in different catalytic processes, such as sulfoxidation [ 3 , 4 ], olefin epoxidations [ 5 , 6 , 7 ], alcohol oxidations [ 8 ], etc. The capability of molybdenum to adapt and easily convert between different oxidation states signals further applications.…”

Section: Introductionmentioning

confidence: 99%

Impedance Spectroscopy as a Powerful Tool for Researching Molybdenum-Based Materials with Schiff Base Hydrazones

et al. 2023

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Molybdenum coordination complexes are widely applied due to their biological and pharmacological potential, as well as their performance in different catalytic processes. Parent dioxidomolybdenum Schiff base complexes were prepared via the reaction of [MoO2(acac)2] with a hydrazone Schiff-base tetradentate ligand. A new hydrazone-Schiff base (H2L1 and 2) and its corresponding mononuclear and polynuclear dioxidomolybdenum(VI) complex were synthesized and characterized by spectroscopic methods and elemental analyses, and their thermal behavior was investigated by thermogravimetry. The crystal and molecular structures of H2L2 ligands and the complexes [MoO2(L1)(H2O)], [MoO2(L2)(H2O)], [MoO2(L1)(MeOH)]∙MeOH, [MoO2(L1)(EtOH)]∙EtOH, [MoO2(L1)(2-PrOH)]∙2-PrOH, and [MoO2(L1)]n were determined by single-crystal X-ray diffraction. Using the in situ impedance spectroscopy method (IS), the structural transformations of chosen complexes were followed, and their electrical properties were examined in a wide range of temperatures and frequencies.

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Section: Introductionmentioning

confidence: 99%

Impedance Spectroscopy as a Powerful Tool for Researching Molybdenum-Based Materials with Schiff Base Hydrazones

et al. 2023

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“…[1][2][3][4][5] Also, due to azomethine moiety, their value has increased in the field of coordination chemistry. This is because they have a wide range of biological properties, [6][7][8][9][10][11][12] as they can form stable structures that can increase the biological effects of ligands through their coordination with many transition metal ions. [13][14][15][16][17] Many complexes of Schiff base ligands with metal ions have been investigated as models for active enzyme sites, [18,19] including DNA cleavage systems, [20] and as antibacterial, anti-inflammatory, antiproliferative, antiviral, antimalarial, antioxidant, antitumoral, and antimycotic compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, potential antimicrobial, antioxidant, anticancer, DNA binding, and molecular docking activities and DFT on novel Co(II), Ni(II), VO(II), Cr(III), and La(III) Schiff base complexes

Abdel‐Rahman

Basha

Al–Farhan

et al. 2021

Applied Organom Chemis

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In this study, five novel complexes for Co(II), Ni(II), VO(II), Cr(III), and La(III) ions were synthesized from a tridentate NNO monobasic chelating Schiff base ligand, (Z)-2-((pyridin-2-ylimino)methyl)phenol (HL). Spectral and analytical tools were applied to elucidate the structural compositions of the new compounds. Then, geometry optimization was conducted for all the syntheses by the Gaussian 09 program via the density functional theory method to obtain optimal structures and the most essential parameters. Moreover, the biochemical behaviors of all the syntheses were explored based on the reactivity, which was tested against various cancer cell lines (HepG-2, MCF-7, and HCT-116). The complexes exhibited an interestingly antiproliferative potential against human cancer cell lines, and the cytotoxicities of the new complexes were arranged to follow the order: VOL > CrL > NiL > LaL > CoL > HL. The antioxidant behaviors of the complexes were studied using the DPPH assay, and VOL showed the maximum antioxidant activity, followed by LaL. The antibacterial activities of the HL ligand and its complexes were studied. Moreover, the binding nature of the complexes with calf thymus DNA (CT-DNA) was investigated based on the spectrophotometric absorption titration, viscosity, and gel electrophoresis methods. The binding ability of the complexes with CT-DNA was proposed to be just intercalation or replacement mode. The intrinsic binding constant K b was calculated and arranged based on the following order: VOL (5.2 Â 10 5 ) > CrL (3.6 Â 10 5 ) > NiL (3.3 Â 10 5 ) > LaL (3.0 Â 10 5 ) > CoL (1.12 Â 10 5 ) mol À1 dm À3 . Docking investigations were performed using the receptors of COVID-19's main protease viral protein (PDB ID: 6LU7) and Escherichia coli (gram [-ve] bacteria [PDB ID: 1fj4]).

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“…Previous attempts of homogenous catalysis were unsuccessful in synthesizing compounds at a large scale, but iron and chiral Schiff base ligands overcame this drawback. [117] The enantioselective sulfoxidation of thioanisole 152 using cis-dioxidomolybdnum (VI) complex with chiral tetradentate Schiff base 154 was reported by Romanowski [118] in 2020. They experimented with CDCl 3 at different temperatures (from 25 to À 20 °C) in the presence of slightly excess (1.1 mol %) t-butyl hydroperoxide (TBHP) or 30 % H 2 O 2 as terminal oxidants.…”

Section: Enantioselective Sulfoxidation Reactionmentioning

confidence: 99%

Recent Advances in the Catalytic Applications of Chiral Schiff‐Base Ligands and Metal Complexes in Asymmetric Organic Transformations

Jain

Barman

2022

ChemistrySelect

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The Schiff base and its metal complexes are extensively studied for their adaptable metal chelating properties. Their ability to alter the design and modify it for various organic and biological applications makes them versatile compounds. The chiral Schiff base and their metal complexes possess excellent stability in very high temperatures, making them a suitable candidate for organocatalysts in reactions involving harsh conditions. Besides, these chiral complexes of Schiff base can transform their chirality in the final product formed in different chemical reactions. This stereo-induction by the chiral metal complexes of Schiff base is considerably valuable for synthesizing high optically active compounds in the field of medicinal and natural product synthesis. Thus, this review emphasizes the latest and relevant literature concerning the asymmetric catalysis of chiral Schiff base ligand-metal complexes in various synthetic organic transformation reactions. The synthesis and the catalytic mechanisms of various reactions are discussed, including their enantioselectivities, diastereoselectivities, regioselectivities, and stereoselectivities of different complexes to organic transformation.

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Cis-dioxidomolybdenum(VI) complexes with chiral tetradentate Schiff bases: Synthesis, spectroscopic characterization and catalytic activity in sulfoxidation and epoxidation

Cited by 16 publications

References 47 publications

Impedance Spectroscopy as a Powerful Tool for Researching Molybdenum-Based Materials with Schiff Base Hydrazones

Impedance Spectroscopy as a Powerful Tool for Researching Molybdenum-Based Materials with Schiff Base Hydrazones

Synthesis, characterization, potential antimicrobial, antioxidant, anticancer, DNA binding, and molecular docking activities and DFT on novel Co(II), Ni(II), VO(II), Cr(III), and La(III) Schiff base complexes

Recent Advances in the Catalytic Applications of Chiral Schiff‐Base Ligands and Metal Complexes in Asymmetric Organic Transformations

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