Imine-based Zwitterion: Synthesis, single-crystal characterization, and computational investigation

Malik, Abida Naseem; Kuznetsov, Aleksey E.; Ali, Akbar; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Siddique, Abu Bakar

doi:10.1016/j.molstruc.2021.132237

Cited by 25 publications

(14 citation statements)

References 52 publications

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“… 36 , 37 The existence of consecutive red and blue triangle areas on the HS around aromatic rings indicates their involvement in π···π stacking interactions. 38 The presence of such regions on the HS indicates the existence of the π···π stacking interactions in FTEAA ( Figure 6 b). However, these π···π stacking interactions are very weak as the intercentroid distance for this interaction ranges from 4.5501 (13) to 5.9959 (12) Å.…”

Section: Resultsmentioning

confidence: 95%

“…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%

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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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Section: Resultsmentioning

confidence: 95%

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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Section: Introductionmentioning

confidence: 99%

“…Imines are also a class of organic chemical architecture that has been reconnoitered by DFT analysis in order to investigate their crucial electronic properties such as non-covalent interaction, nonlinear optical properties, and so forth . The computational tool has also been applied to the imine-based zwitterion compounds in order to explore its stability (supported by NBO investigations) accompanied with reactivity in the redox process …”

Section: Introductionmentioning

confidence: 99%

“…14 The computational tool has also been applied to the imine-based zwitterion compounds in order to explore its stability (supported by NBO investigations) accompanied with reactivity in the redox process. 15 Herein, we are presenting our findings toward the synthesis, DFT study, and crystal packing of the crystalline imine/Schiff base compounds: (E)-2-methoxy-6-(((3-(trifluoromethyl) phenyl)imino)methyl)phenol (MFIP) and (E)-1-(((2fluorophenyl)imino)methyl)naphthalen-2-ol (FPIN).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

et al. 2022

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This investigation is focused on the synthesis of two halo-functionalized crystalline Schiff base (imine) compounds: ( E )-2-methoxy-6-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol ( MFIP ) and ( E )-1-(((2-fluorophenyl)imino)methyl)naphthalen-2-ol ( FPIN ) by the condensation reaction of substituted benzaldehydes and substituted aniline. The crystal structures of MFIP and FPIN were determined unambiguously by single-crystal X-ray diffraction (SC-XRD) studies. Intermolecular interactions and the role of fluorine atoms in the stabilization of the crystal packing are explored for both compounds using Hirshfeld surface analysis. Accompanied with experimental studies, quantum chemical calculations were also performed for comprehensive structure elucidation at the M06/6-311G(d,p) level of theory. A comparison of experimental and density functional theory results for geometrical parameters exhibited excellent agreement. Interestingly, Frontier molecular orbitals and natural bond orbital (NBO) findings revealed that intramolecular charge transfer and hyper-conjugation interactions had played a significant role to stabilize the molecules. Both compounds exhibited a relatively larger value of hardness with a smaller global softness, which, as proposed by the SC-XRD and NBO study, shows a higher stability. Nonlinear optical (NLO) findings showed that FPIN manifested a larger value of linear polarizability (< a > = 293.06 a.u.) and second-order hyperpolarizability (<γ> = 3.31 × 10 5 a.u.) than MFIP (< a > = 252.42 and <γ> = 2.08 × 10 5 a.u.) due to an extended conjugation. The above-mentioned findings of the entitled compounds may play a crucial role in NLO applications.

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Synthesis, crystal structure, Hirshfeld surface, nonlinear optical properties and computational studies of Schiff based (E)-N'-(2,4-dimethoxybenzylidene) benzohydrazide single crystals for optoelectronic applications

Saraswathi¹,

Agilan²,

Muthukumarasamy³

et al. 2022

Opt Quant Electron

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Imine-based Zwitterion: Synthesis, single-crystal characterization, and computational investigation

Cited by 25 publications

References 52 publications

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

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

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

Synthesis, crystal structure, Hirshfeld surface, nonlinear optical properties and computational studies of Schiff based (E)-N'-(2,4-dimethoxybenzylidene) benzohydrazide single crystals for optoelectronic applications

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