Zn(II) complexes containing O,N,N,O-donor Schiff base ligands: synthesis, crystal structures, spectral investigations, biological activities, theoretical calculations and substitution effect on structures

Kargar, Hadi; Fallah‐Mehrjardi, Mehdi; Ashfaq, Muhammad; Munawar, Khurram Shahzad; Tahir, Muhammad Nawaz; Behjatmanesh–Ardakani, Reza; Rudbari, Hadi Amiri; Ardakani, Amir Adabi; Sedighi-Khavidak, Samaneh

doi:10.1080/00958972.2021.1990271

Cited by 36 publications

(12 citation statements)

References 71 publications

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“…22,23 One can see a strong peak at 910 cm −1 which is assignable to a Zn−N stretching vibration. 24 The above results suggest that there is coordination between Hatm and Zn in ZnBr 2 −Hatm. 22 The fresh and reused ZnBr The N 1s and Zn 2p spectra of ZnBr 2 −Hatm are displayed in Figure 4.…”

Section: Methodsmentioning

confidence: 76%

“…The band at 671 cm –1 in the case of Hatm is attributed to the C–N–C bending vibration of free Hatm ligand. In the case of ZnBr 2 –Hatm, there are two distinct peaks at 650 and 679 cm –1 corresponding to C-N(Zn)-C and C-N(C)-C, respectively. , The bands at 813 and 1012 cm –1 of Hatm because of the C–N stretching vibration become peaks at 773, 850, 980, 999, 1032, and 1056 cm –1 when it comes to ZnBr 2 –Hatm. , One can see a strong peak at 910 cm –1 which is assignable to a Zn–N stretching vibration . The above results suggest that there is coordination between Hatm and Zn in ZnBr 2 –Hatm .…”

Section: Resultsmentioning

confidence: 98%

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Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO₂ under Mild Conditions

Lan

Chen

Zhu

et al. 2022

Ind. Eng. Chem. Res.

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In terms of the multisynergetic effects among Lewis acid, halogen anions, and Lewis base, a series of Lewis acid−base hexamethylenetetramine complexes with tertiary amines, different metal centers, and halogen anions were conveniently synthesized at room temperature. Hexamethylenetetramine is cheap, nontoxic, rich in tertiary amine, and with a cage structure. This is the first time that the hexamethylenetetramine complexes were used as efficient and stable heterogeneous catalysts for the generation of cyclic carbonates by the coupling reaction of CO 2 under relatively mild conditions (60 °C, 1.5 MPa, 12 h) with outstanding performance (yield = 98.9%) without use of solvent and cocatalyst. Hatm complexes that are different in nucleophilicity and Lewis acidity are designed and evaluated, which suggest that the stronger Lewis acidity of metal together with stronger nucleophilicity of anions means higher catalytic performance. A plausible multisynergetic mechanism over ZnBr 2 −Hatm is proposed for the CO 2 coupling. In addition, the ZnBr 2 −Hatm can be conveniently recovered and reused in a test of five times without remarkable decline of activity.

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Section: Methodsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 98%

Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO₂ under Mild Conditions

Lan

Chen

Zhu

et al. 2022

Ind. Eng. Chem. Res.

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“…The green dotted lines in Figure a represent H-bonding interactions. π···π stacking interactions can be visualized by HS that is plotted over the shape index. , The existence of consecutive red and blue triangle areas on the HS around aromatic rings indicates their involvement in π···π stacking interactions . The presence of such regions on the HS indicates the existence of the π···π stacking interactions in FTEAA (Figure b).…”

Section: Resultsmentioning

confidence: 99%

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

et al. 2022

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Ethyl 4-(4-fluorophenylamino)-2,6-bis(4-(trifluoromethyl)phenyl)-1-(4-fluoro-phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate ( FTEAA ) has been synthesized efficiently in an iodine-catalyzed five-component reaction of 4-fluoroaniline, 4-trifluoromethyl benzaldehyde, and ethyl acetoacetate in methanol at 55 °C for 12 h. Various spectro-analytical techniques such as 1 H and 13 C NMR and Fourier-transform infrared spectroscopy have validated the structure of FTEAA . Further confirmation of the structure of FTEAA has been established on the basis of single-crystal X-ray diffraction analysis. The supramolecular assembly of FTEAA in terms of strong and comparatively weak noncovalent interactions is fully investigated by Hirshfeld surface analysis, the interaction energy between pairs of molecules, and energy frameworks. The void analysis is conducted to explore the strength and stability of the crystal structure. Furthermore, molecular docking analysis was computationally performed to see the potential intermolecular interactions between the selected proteins and FTEAA . The binding interaction energies are found to be −8.8 and −9.6 kcal/mol for the proteins MAO-B (PDB ID: 2V5Z ) and MAO-A (PDB ID: 2Z5X ), respectively. These reasonably good binding energies (more negative values) indicate the efficient associations between the FTEAA and target proteins. The proteins and FTEAA were also analyzed for intermolecular interactions. FTEAA and proteins interact in a variety of ways, like conventional hydrogen bonds, carbon–hydrogen bonds, alkyl, π-alkyl, and halide interactions.

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“…The shape index property was used to map the HS views of DC2H and DM4H , which represent the red and blue triangular regions shown in Figure c,d, respectively. Here, bright-red spots indicate the π···π stacking between the six-membered rings. , Similarly, HS curvedness mapping also shows the π···π stacking, which is obvious because of the flat regions around the carbon rings (Figure S3a,b). Figure e,f shows the electrostatic potential, while Figure g,h shows the deformation density for DC2H and DM4H , respectively.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The red spots (bright and faint) can be classified as potential hydrogen bonds. The shape index property was used to map the HS views of DC2H and DM4H, which represent the red and blue triangular regions shown in Figure 5c,d, respectively.Here, bright-red spots indicate the π•••π stacking between the six-membered rings 33,34. Similarly, HS curvedness mapping also shows the π•••π stacking, which is obvious because of the…”

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confidence: 99%

Shedding Light on the Synthesis, Crystal Structure, Characterization, and Computational Study of Optoelectronic Properties and Bioactivity of Imine derivatives

et al. 2022

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Two imine compounds named as (E)-2-(((3,4dichlorophenyl)imino)methyl)phenol (DC2H) and (E)-4-(((2,4dimethylphenyl)imino)methyl)phenol (DM4H) are synthesized, and their crystal structures are verified using the single-crystal X-ray diffraction (XRD) technique. The crystal structures of the compounds are compared with the closely related crystal structures using the Cambridge Structural Database (CSD). The crystal packing in terms of intermolecular interactions is fully explored by Hirshfeld surface analysis. Void analysis is carried out for both compounds to check the strength of the crystal packing. Furthermore, a state-of-the-art dual computational technique consisting of quantum chemical and molecular docking methods is used to shed light on the molecular structure, optoelectronic properties, and bioactivity of indigenously synthesized compounds. The optimized molecular geometries are compared with their counterpart experimental values. Based on previous reports of biofunctions of the indigenously synthesized imine derivatives, they are explored for their potential inhibition properties against two very crucial proteins (main protease (M pro ) and nonstructural protein 9 (NSP9)) of SARS-CoV-2. The calculated interaction energy values of DC2H and DM4H with M pro are found to be −6.3 and −6.6 kcal/mol, respectively, and for NSP9, the calculated interaction energy value is found to be −6.5 kcal/mol. We believe that the current combined study through experiments and computational techniques will not only pique the interest of the broad scientific community but also evoke interest in their further in vitro and in vivo investigations.

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Zn(II) complexes containing O,N,N,O-donor Schiff base ligands: synthesis, crystal structures, spectral investigations, biological activities, theoretical calculations and substitution effect on structures

Cited by 36 publications

References 71 publications

Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO₂ under Mild Conditions

Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO₂ under Mild Conditions

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

Shedding Light on the Synthesis, Crystal Structure, Characterization, and Computational Study of Optoelectronic Properties and Bioactivity of Imine derivatives

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Zn(II) complexes containing O,N,N,O-donor Schiff base ligands: synthesis, crystal structures, spectral investigations, biological activities, theoretical calculations and substitution effect on structures

Cited by 36 publications

References 71 publications

Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO2 under Mild Conditions

Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO2 under Mild Conditions

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

Shedding Light on the Synthesis, Crystal Structure, Characterization, and Computational Study of Optoelectronic Properties and Bioactivity of Imine derivatives

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Product

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Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO₂ under Mild Conditions

Hexamethylenetetramine Complexes as Easy-to-Handle and Efficient Lewis Acid–Base Heterogeneous Catalysts for Coupling of CO₂ under Mild Conditions