Crystal structures, electrochemical properties and theoretical studies of three New Zn(II), Mn(III) and Co(III) Schiff base complexes derived from 2-hydroxy-1-allyliminomethyl-naphthalen

Ramezanipoor, Sahar; Parvarinezhad, Sakineh; Salehi, Mehdi; Grześkiewicz, Anita M.; Kubicki, Maciej

doi:10.1016/j.molstruc.2022.132541

Cited by 13 publications

(22 citation statements)

References 44 publications

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“…Fingerprint diagrams are also drawn based on d i and d e distances and provide the percentage of participation of various intermolecular interactions. [54][55][56]60]…”

Section: Hs Analysismentioning

confidence: 99%

Experimental and theoretical studies of new Co(III) complexes of hydrazide derivatives proposed as multi‐target inhibitors of SARS‐CoV‐2

Parvarinezhad

Salehi

Kubicki

et al. 2022

Applied Organom Chemis

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Cobalt(III) complexes with Schiff base ligands derived from hydrazone, (HL 1 = (E)-N 0 -(3,5-dichloro-2-hydroxybenzylidene)-4-hydroxybenzohydrazide, HL 2 = (E)-N 0 -(3,5-dichloro-2-hydroxybenzylidene)-4-hydroxybenzohydrazide (3,5-dibromo-2-hydroxybenzylidene), and HL 3 = (E)-4-hydroxy-N 0 -(2-hydroxy-3-ethoxybenzylidene)benzohydrazide), were synthesized and characterized by elemental analysis, Fourier transform infrared (FT-IR) spectroscopy, UV-Vis spectroscopy, and cyclic voltammetry. X-ray diffraction was used to determine the single crystal structure of the complex (1). Co(III) was formed in a distorted, very regular octahedral coordination in this complex; three pyridine moieties complete this geometry. Schiff base complexes' redox behaviors are represented by irreversible (1), quasi-reversible (2), and quasi-reversible (3) voltammograms. A density functional theory (DFT)/B3LYP method was used to optimize cobalt complexes with a base set of 6-311G. Furthermore, fragments occupying the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) were investigated at the same theoretical level. Quantum theory of atoms in molecules (QTAIM) computations were also done to study the coordination bonds and non-covalent interactions in the investigated structures. Hirshfeld surface analysis was used to investigate the nature and types of intermolecular exchanges in the crystal structure of the complex (1). The capacity of cobalt complexes to bind to the major protease SARS-CoV-2 and the molecular targets of human angiotensin-converting enzyme-2 (ACE-2) was investigated using molecular docking. The molecular simulation methods used to assess the probable binding states of cobalt complexes revealed that all three complexes were stabilized in the active envelope of the enzyme by making distinct interactions with critical amino acid residues. Interestingly, compound (2) performed better with both molecular targets and the total energy of the system than the other complexes. K E Y W O R D S4-hydroxybenzohhydrazide, Co(III) complex, electrochemical properties, theoretical study, X-ray crystallography

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“…Fingerprint diagrams are also drawn based on d i and d e distances and provide the percentage of participation of various intermolecular interactions. [54][55][56]60]…”

Section: Hs Analysismentioning

confidence: 99%

Experimental and theoretical studies of new Co(III) complexes of hydrazide derivatives proposed as multi‐target inhibitors of SARS‐CoV‐2

Parvarinezhad

Salehi

Kubicki

et al. 2022

Applied Organom Chemis

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“…According to the FT-IR spectrum of the Schiff base complexes in Figure S2, S3 and S4, it has a shift compared to the stretching vibration bands in the ligand, which con rms the synthesis of the complex. The stretching vibration band of the C = N group in these complexes was observed at a wave number lower than that of the ligand in the regions of 1618 (1, 2), 1616 (3), and 1606 (4) cm − 1 [14,15]. The stretching vibration band in the regions of 1355 (1, 2), 1361 (3) and 1361 cm − 1 (4) is attributed to the C─O band.…”

Section: Ft-ir Spectramentioning

confidence: 87%

“…In addition, metal-nitrogen and metal-oxygen absorption bands appeared in the regions of 421-580 cm − 1 (1, 2), 481-572 cm − 1 (3) and 414-524 cm − 1 (4), respectively. The broad absorption band in the regions of 2760-3190 cm − 1 was attributed to C─H stretching vibration [14,15,[31][32][33].…”

Section: Ft-ir Spectramentioning

confidence: 99%

“…(3), 438 nm (4) are related to the charge transfer. For complexes (3,4) in the 484 and 675 nm districts, d → d transfers was observed, respectively [13][14][15][34][35][36].…”

Section: Uv-vis Spectramentioning

confidence: 99%

“…Abbasi et al synthesized Ni(II), Cu(II) and V(IV) complexes by 2-hydroxy 1-naphthaldehyde and 2-methoxyethylamine derivatives and studied the anticancer activity of these compounds against gastric cancer [14]. Docking studies on Schiff base complexes obtained from 2-hydroxy 1-naphthaldehyde and allylamine were performed in 2016 and 2022, the results obtained from molecular docking showed that the presence of metal in the compounds causes that compounds are attached to the amino acid in a suitable orientation and binding [13,15]. Didarul A. Chowdhury and co-workers synthesized dioxouronium(VI) complexes of derivatives, 2hydroxy-1-naphthaldehyde, each of which Schiff base complexes are bivalent anions with tridentate ONS donors [16].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, spectra, crystal structure, Hirshfeld surface analysis, DFT calculations and molecular docking evaluation on novel mononuclearZn(II), Mn(III) and Co(III) Schiff base complexes derived from 2- hydroxy-1-naphthaldehyde

Parvarinezhad

Ramezanipoor

Kubicki

et al. 2023

Preprint

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four novel complexes of bidentate Schiff base ligand derived from 2-hydroxy-1-(2-methoxyethylimino)-naphthalen (HL) were synthesized and characterized using elemental analysis, FTIR, and UV–Vis spectroscopies. X-ray single crystal structures of Zn(II), Mn(III) and Co(III) complexes (1–4) have also been determined, and it was indicated that these Zn(II) and Co(III) complexes (1, 4) are in an octahedral geometry. Whereas, it was found that the Zn complex (2) in quite a regular tetrahedral environment. Also, Mn center in complex (3), is ligated by two azomethine nitrogen atom, two ligand oxygen atoms and one Cl atom of metal salt forming five coordinated tetragonal pyramid geometry around of the Mn atoms. The cyclic voltammetry (CV) of the complexes specifies an irreversible redox behavior for all complexes (1–4). Next, the molecular electrostatic potential (MEP) was studied for all complexes to better understand and predict the reaction sites of electrophilic and nucleophilic attacks. Also, density functional theory (DFT) calculations were performed to determine the optimal geometrical configurations, and comparison between experimental and theoretical data, and non-covalent interactions were determined by Hirshfeld surface analysis (HSA) using CrystalExplorer program. Also, finding binding affinity of complexes with protein (PDB ID: 4LXD) was also done using molecular docking.

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Novel dinuclear Ni (II) Schiff base complexes induced noncovalent exchanges: Crystal structure investigation, electrochemical assessment, Hirshfeld surface analysis and SARS‐CoV‐2 docking study

Roozbahani,

Malekshah,

Salehi

et al. 2023

Applied Organom Chemis

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In this work, novel Ni (II) complexes, namely, [Ni2(L)2(OAc)2(EtOH)2] (1a), [Ni2(L)2(OAc)2(H2O)2] (1b‐1) and [Ni2(L)2(OAc)2(EtOH)2] (1b‐2) as co‐crystal were synthesized by the 1:1 condensation (https://www.sciencedirect.com/topics/chemistry/condensation) of Ni (CH3COO)2·4H2O and Schiff base ligand (H2L) (2‐hydroxy‐4‐methoxybenzaldehyde and 2‐amino‐2‐methylpropanol). The ligand based on Schiff base and fabricated complexes (1a) and (1b‐1 and 1b‐2) were successfully identified by CHN assessment, FT‐IR, UV–Vis spectra, melting point and CV voltammogram. The electrochemical behavior investigation shows that the nickel complexes exhibited irreversible oxidation processes in methanol solution. Additionally, the crystal structures of complexes (1a) and (1b) have been recognized by single‐crystal X‐ray diffraction investigation. It turned out that the complexes (1b‐1) and (1b‐2) crystallize together, making a co‐crystal 1b with an additional EtOH solvent molecule in the crystal structure. A detailed study of intermolecular exchanges was performed using attractive graphical analysis tools such as three‐dimensional Hirshfeld surfaces analysis, two‐dimensional fingerprint plots (FPs), and enrichment ratios (E), which make C‐H … C, C‐H … O hydrogen bond, C … O, H … H, and O … O short contacts on Hirshfeld surfaces with color code are observed. Moreover, an appraisement of the inhibitory trace against coronavirus (main protease SARS‐CoV‐2, PDB ID: 6Y2F) and molecular targets of human angiotensin‐converting enzyme‐2 (ACE‐2) was performed by a molecular docking study in which two nickel complexes performed best for PDB protein ID: 6M0J and all three complexes for PDB protein ID: 6Y2F.

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Crystal structures, electrochemical properties and theoretical studies of three New Zn(II), Mn(III) and Co(III) Schiff base complexes derived from 2-hydroxy-1-allyliminomethyl-naphthalen

Cited by 13 publications

References 44 publications

Experimental and theoretical studies of new Co(III) complexes of hydrazide derivatives proposed as multi‐target inhibitors of SARS‐CoV‐2

Experimental and theoretical studies of new Co(III) complexes of hydrazide derivatives proposed as multi‐target inhibitors of SARS‐CoV‐2

Synthesis, spectra, crystal structure, Hirshfeld surface analysis, DFT calculations and molecular docking evaluation on novel mononuclearZn(II), Mn(III) and Co(III) Schiff base complexes derived from 2- hydroxy-1-naphthaldehyde

Novel dinuclear Ni (II) Schiff base complexes induced noncovalent exchanges: Crystal structure investigation, electrochemical assessment, Hirshfeld surface analysis and SARS‐CoV‐2 docking study

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