Some newly synthesized ferrocene based esters: Characterization, DNA interaction and DFT studies

Nisa, Zaib Un; Gul, Asghari; Akhter, Zareen; Nadeem, Muhammad Arif; Tahir, Muhammad Nawaz; Ahmed, Moiz Uddin

doi:10.1016/j.jorganchem.2016.07.027

Cited by 7 publications

(7 citation statements)

References 24 publications

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“…The aromatic ring seems neutral in terms of electron density. Thus distribution of potential is in favor of the complexation reaction which is further confirmed by electrostatic potential distribution of zinc(II) complex, where a greater negative charge is surrounded to the metal center (Figure b). The Mulliken electronegativity (Figure and supplementary Table 3) also indicated the increase of electronegativity of oxygen and nitrogen in zinc(II) complex than free H 2 L making them the favour site of electrophilic attack by metal ion.…”

Section: Resultsmentioning

confidence: 57%

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Coordination compounds of some transition metal ions with new Schiff base ligand derived from dibenzoyl methane. Structural characterization, thermal behavior, molecular structure, antimicrobial, anticancer activity and molecular docking studies

Mahmoud

El-Sayed

2017

Applied Organom Chemis

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Series of Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes were prepared with tetradentate Schiff base ligand derived by condensation of 2‐aminophenol with dibenzoylmethane. The novel Schiff base H2L (2–2′‐((1Z,1Z’)‐(1,3‐diphenyl propane‐1,3 diylidene) bis (azanylylidene) diphenol) and its binary metal complexes were characterized by physicochemical procedures i.e. elemental analysis, FT‐IR, UV–Vis, thermal analyses (TGA/DTG), mass spectrometry, magnetic susceptibility and conductometric measurements. On the basis of these studies, an octahedral geometry for all these complexes was proposed expect Ni(II) complex which had tetrahedral geometry. Molar conductivity values revealed that the complexes were electrolytes except Mn(II), Zn(II) and Cd(II) complexes were non electrolytes. The ligand bound to the metal ions via two azomethine N and two phenolic OH as indicated from the IR and 1H NMR spectral study. The molecular and electronic structures of H2L and its zinc complex were optimized theoretically and the quantum chemical parameters were calculated. The antimicrobial activity against a number of bacterial organisms as Streptococcus pneumonia, Bacillus Subtilis, Pseudomonas aeruginosa and Escherichia coli and fungi as Aspergillus fumigates, Syncephalastrum racemosum, Geotricum candidum and Candida albicans by disk diffusion method were screened for the Schiff base and its complexes. The Cd(II) complex has potent antimicrobial activity. Anticancer activity of the Schiff base ligand and its metal complexes were evaluated in human cancer (MCF‐7 cells viability). The Cr(III) complex exhibited higher activity than other complexes and ligand. Molecular docking was used to predict the binding between Schiff base ligand (H2L) and its Zn(II) complex and the receptors of RNA of amikacin antibiotic (4P20) and human‐DNA‐Topo I complex (1SC7). The docking study provided useful structural information for inhibition studies.

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Section: Resultsmentioning

confidence: 57%

“…Based on the MEP, one can generally order the electron‐rich area which has red color on the map (favor site for electrophilic attack). However, the electron‐poor region has blue color (favor site for nucleophilic attack) . But the region with green color points to neutral electrostatic potential region.…”

Section: Resultsmentioning

confidence: 99%

Coordination compounds of some transition metal ions with new Schiff base ligand derived from dibenzoyl methane. Structural characterization, thermal behavior, molecular structure, antimicrobial, anticancer activity and molecular docking studies

Mahmoud

El-Sayed

2017

Applied Organom Chemis

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“…Chromatographic separations were performed employing silica gel 60 (AVRA, 60–120 mesh) as the stationary phase. Chromophore 1 was synthesised according to the literature [27] and 2 was synthesised by Suzuki Miyaura cross‐coupling reaction, as shown in Scheme S1.…”

Section: Methodsmentioning

confidence: 99%

AIE‐Active Ferrocene Appended Linear (D‐π‐A) Aromatic Ester Chromophores: Structural, Theoretical and Effect on Phenyl Ring on Luminescence and Nonlinear Optical Properties

Chithra,

Prabu,

Babu

et al. 2024

ChemistrySelect

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In the present research, a new ferrocene‐appended linear donor‐π‐acceptor (D‐π‐A) ester chromophore Fc‐(C6H4)2‐COOC2H5 (2) was synthesized and characterized using various spectroscopic techniques. The molecular structure of chromophore 2 was determined using single‐crystal X‐ray diffraction analysis, revealing its crystallization in the monoclinic crystal system with the P21/n space group. The chromophore Fc‐C6H4‐COOC2H4 (1) was utilized to compare its photophysical and nonlinear optical characteristics with those of 2. Cyclic voltammetry revealed a single‐electron transfer mechanism from Fe2+↔Fe3+. The emission solvatochromism studies show a polarized excited state in response to increasing solvent polarity, indicating charge transfer processes. Interestingly, in mixed aqueous media (THF/H2O), the chromophores exhibit intensified fluorescence due to restricted intra‐molecular rotation (RIR), despite weak emission in THF solvent. Chromophore 2 demonstrated 1.5 times higher second harmonic generation (SHG) efficiency than 1, attributed to its extended π‐conjugation from an additional phenyl ring and reduced antiparallel alignments. Despite its centrosymmetric crystal packing, chromophore 2 exhibited SHG efficiency due to non‐covalent interactions (C−H⋅⋅⋅π) in the crystal lattice. Density Functional Theory (DFT) calculations, employing various functionals, provided insights into dipole moment and first hyperpolarizability, with B3LYP‐hybrid functional underestimating hyperpolarizability values owing to long‐range charge transfer interactions within the D‐π‐A systems, aligning closely with experimental findings.

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“…According to colour grading style, three donating atoms upon the ligand surface displayed electron-rich sites which has red colour (favour site for Metallic shape, besides electrostatic potential in color grading style, thus able to predict active electrophilic attack), thus the compound is tridentate ligand (Figure 4). However, the electronpoor sites has blue color (favor site for donor atoms nucleophilic attack) [49]. Furthermore, reactivity parameters such as total energy and HOMO and LUMO energies are calculated in addition to selected quantum chemical parameters of Schiff base ligand (HL) are tabulated in Table (3), as ΔE, absolute electronegativities, v, chemical potentials, Pi, absolute hardness, g, absolute softness, r, global electrophilicity, x, global softness, S, and additional electronic charge, ΔNmax, were calculated according to the following equations: (8) Electrophilicity index (ω) determines toxicity and the reactivity of various active sites.…”

Section: Geometry Optimization 381 Optimized Molecular Structures Of Schiff Basementioning

confidence: 99%

“…η and σ indexes, represent the molecular stability and reactivity. The softness indexes and global hardness are the vice versa image for each other [49,50]. The positive, high electrophilicity index (χ) value reflected the biological reactivity of ligand and stability , besides the electronic chemical potential must be negative [51].…”

Section: Geometry Optimization 381 Optimized Molecular Structures Of Schiff Basementioning

confidence: 99%

Studying of physicochemical properties of Coumarin based Nano-complexes for biomedical applications

2021

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Novel Schiff base ligand based on coumarin precursor was prepared by the condensation of 3-acetyl coumarin with 3-aminophenol. The newly synthesized Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes were characterized by elemental analysis, molar conductivity, spectroscopic techniques (IR, 1 H NMR, mass spectrometry, UV-Vis), and thermal analysis (TG/DTG) to predict their structures. The resulting data displays octahedral complexes with 1M:1L ratio. The IR confirmed that the ligand coordinated to the metal ions in tridentate mode with ONO coordination sites. The complexes decomposed with three to five steps within the temperature range 30-900 C. Additionally, mass spectra of the ligand and its Cu(II) complex offer well matching data with calculated value. The molar conductivity values pointed out that the complexes were non-electrolytes. Molecular optimization of prepared compositions at DFT/ LANL2DZ level, besides Molecular docking between Schiff base ligand (HL) and the receptors of breast cancer were executed. Additionally, antibacterial activity has been evaluated against Streptococcus aureus and Escherichia coli. Additionally, fungicidal activity was screened in vitro against Aspergillus flavus and Candida albicans, using the disc diffusion method. The [Co(HL)Cl2.H2O].4H2O complex exhibits the highest antimicrobial effect against Streptococcus aureus with inhibition area 17mm, while against Escherichia coli it records 14mm, and 12mm against Candida albicans. The [Mn(L)Cl2.H2O].4H2O complex shows the lowest IC50 against human cancer (MCF-7 cells viability) with 22.2 µg/ml.

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Some newly synthesized ferrocene based esters: Characterization, DNA interaction and DFT studies

Cited by 7 publications

References 24 publications

Coordination compounds of some transition metal ions with new Schiff base ligand derived from dibenzoyl methane. Structural characterization, thermal behavior, molecular structure, antimicrobial, anticancer activity and molecular docking studies

Coordination compounds of some transition metal ions with new Schiff base ligand derived from dibenzoyl methane. Structural characterization, thermal behavior, molecular structure, antimicrobial, anticancer activity and molecular docking studies

AIE‐Active Ferrocene Appended Linear (D‐π‐A) Aromatic Ester Chromophores: Structural, Theoretical and Effect on Phenyl Ring on Luminescence and Nonlinear Optical Properties

Studying of physicochemical properties of Coumarin based Nano-complexes for biomedical applications

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