Crystal structures, spectroscopic and theoretical study of novel Schiff bases of 2-(methylthiomethyl)anilines

Olalekan, Temitope E.; Adejoro, Isaiah Ajibade; VanBrecht, Bernardus; Watkins, Gareth M.

doi:10.1016/j.saa.2014.12.018

Cited by 11 publications

(7 citation statements)

References 60 publications

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“…which lie in the range of tetrahedral stereochemistry (4.1-4.8 B.M.). The spectrum of nickel (II) complex showed four bands at 35,080, 31,250, 270,270 cm À1 , and weak one at 18,865 cm À1 due to charge transfer and the three spinallowed electronic transitions to the excited triplet states, 3 A 2 ! 3 T 2 (F), 3 A 2 !…”

Section: Spectral Studiesmentioning

confidence: 99%

“…Schiff base transition metal complexes are one of the most adaptable and thoroughly studied systems. [2][3][4][5] The change of color of thermochromic compounds is ascribed to the tautomerism between the OH and CN forms resulting from intramolecular proton transfer between an enolimine and a ketoamine tautomer, which can be cis or trans relative to the C=N bond (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, molecular docking, biological activity, and DNA cleavage studies of Cu(II), Co(II), Ni(II), Mn(II), and Cd(II) Schiff base complexes

El‐Sonbati

Diab

El-Sayed

et al. 2022

Applied Organom Chemis

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Metal complexes of Schiff base ligand 4-((Z)-(4-nitrophenylimino)methyl)benzene-1,3-diol (H 2 L) derived from condensation of 2,4-dihydroxybenzaldehyde and p-nitroaniline were synthesized and characterized by elemental analysis, IR, 1 H NMR spectra, magnetic moment, molar conductance, and ultraviolet (UV)-Visible and thermal analysis. The complexes were proposed to have the formula [M (HL)(OAc) 2 ] where M = Cu (II), Co(II), Ni(II), Mn(II), and Cd(II). The Fourier transform infrared (FT-IR) spectra showed that ligand is coordinated to the metal ions in bidentate manner with donor sites of the azomethine-N, phenolic-OH. The synthesized Schiff base ligand and its metal complexes (1)-( 5) were screened for their antibacterial activity. Antifungal activities were determined against Fusarium oxysporum, Aspergillus niger, and Candida albicans. Complex (5) showed a high potential cytotoxic activity against growth human lung cancer tumor cell lines. The DNA cleavage properties of the ligand and its complexes have been investigated by gel electrophoresis whose results showed that the Cu(II) complex has a significant oxidative cleavage among other complexes. Addition of H 2 O 2 to the cleavage reaction enhanced the complete DNA degradation for Cu(II) and Co(II) complexes and DNA cleavage for Mn(II) complex. Molecular docking study between the ligand and the receptors (Escherichia coli [3t88], Staphylococcus aureus [3q8u],prostate cancer [2q7l Hormone], breast cancer [1jnx Gene regulation], lung cancer [1x2j], and colon cancer [2hq6]) was carried out, and it was found that the ligand is an efficient compound for all these receptors.

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Section: Spectral Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, molecular docking, biological activity, and DNA cleavage studies of Cu(II), Co(II), Ni(II), Mn(II), and Cd(II) Schiff base complexes

El‐Sonbati

Diab

El-Sayed

et al. 2022

Applied Organom Chemis

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“…The important and relevant bands in the infrared spectra of LH 2 and metal complexes are recorded on Table 2. In the ligand, the broad bands around 3476 and 3257 cm -1 were assigned to aromatic υ (O-H) while the δ (O-H) vibrations appeared as medium bands at 1336 and 622 cm -1 (Sakar, 2009;Olalekan et al, 2015;Smith, 1998).The frequency of the absorption band at 3257 cm -1 was lowered to the range 3228-3100 cm -1 in the complexes; this indicated the participation of the phenol oxygen (C-O) in chelation. The bending vibrational modes were however unaffected, being found in the ranges 1336-1333and 621-619 cm -1 .…”

Section: Infrared Spectramentioning

confidence: 99%

Article 32

2019

sfj

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The Schiff base (LH 2) was prepared by the equimolar reaction of o-phenylenediamine with mhydroxybenzaldehyde under reflux conditions. The metal (II) complexes were prepared by reacting the Schiff base with the metal (II) salts of Fe, Co, and Cu. NMR, IR, UV/Vis, CHN elemental analysis and magnetic moments were used to characterize the compounds. The formulas of the metal complexes were proposed using CHN analysis. In the metal (II) complexes the bands due to υ (O-H) and v (C-O) were shifted to lower wavenumbers and the new medium band assigned to v(M-O)indicated the coordination of the ligand to the metal ions through the phenolate oxygen. In the UV region, the intra ligand π→π* (phenyl ring) and n→π* (-C=N) transitions appeared as medium bands at 299 and 316 nm in the ligand. The metal (II) complexes also exhibit these bands as well as d→d transitions, which suggested tetrahedral coordination of the ligands to the metal ions. The magnetic moments obtained supported the tetrahedral geometries for the paramagnetic metal complexes. The inhibitory activity of the test compounds against Staphylococcus aureus and Pseudomonas aeruginosa observably improved upon chelation. The ligand and metal (II) complexes exhibited better antifungal (12-18 mm) than antibacterial activity (8-18 mm).The positive controls, Gentamicin and Ketoconazole, showed diameters of zones of inhibition at 22-26 mm and 28 mm respectively.

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“…In recent years, Imine based compounds have received much attention in clinical, biological, pharmaceuticals and analytical fields due to the similar structure of naturally occurring biological substances [1,2] and synthetic flexibility [3]. 2-Amino benzothiazole derivatives have received considerable attention owing to their unique structures and exquisite pharmacophores observed in many diagnostic and therapeutic agents [4].…”

Section: Introductionmentioning

confidence: 99%

2-((E)-(6-fluorobenzo[d]thiazol-2-ylimino) methyl)-4-chlorophenol; synthesis, characterization, crystal structure, Hirshfeld surface analysis and BSA binding studies

Kumar

Chidananda

Doddarevanna

et al. 2017

Journal of Molecular Structure

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A new imine-based molecule 2-((E)-(6-fluorobenzo[d]thiazol-2-ylimino) methyl)-4chlorophenol (FBt) was synthesized by microwave and conventional method. It was structurally characterized by spectral techniques (NMR, FT-IR, LC-MS and electronic absorption), elemental analysis and single-crystal X-ray diffraction methods. Hirshfeld surface analysis was employed to ensure the existence of intermolecular interactions in FBt structure. A preliminary in vitro susceptibility test against two pathogenic fungi with respect to standard has shown that the ligand is proved to be a potent antifungal agent. Since the carrying of a drug by BSA may effect on its structure and action, the investigation on the interaction between model protein BSA and FBt was carried out by employing UV-Vis and fluorescence spectroscopy. The characteristics of the binding, i.e., binding constant, number of binding sites, and nature of binding were determined. Besides, the Förster's parameters associated with the binding process were calculated. Molecular docking was also carried on interaction study of the FBt with BSA.

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Crystal structures, spectroscopic and theoretical study of novel Schiff bases of 2-(methylthiomethyl)anilines

Cited by 11 publications

References 60 publications

Synthesis, characterization, molecular docking, biological activity, and DNA cleavage studies of Cu(II), Co(II), Ni(II), Mn(II), and Cd(II) Schiff base complexes

Synthesis, characterization, molecular docking, biological activity, and DNA cleavage studies of Cu(II), Co(II), Ni(II), Mn(II), and Cd(II) Schiff base complexes

Article 32

2-((E)-(6-fluorobenzo[d]thiazol-2-ylimino) methyl)-4-chlorophenol; synthesis, characterization, crystal structure, Hirshfeld surface analysis and BSA binding studies

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