Single crystal inspection, Hirshfeld surface investigation and DFT study of a novel derivative of 4-fluoroaniline: 4-((4-fluorophenyl)amino)-4-oxobutanoic acid (BFAOB)

Ashfaq, Muhammad; Munawar, Khurram Shahzad; Bogdanov, Georgii; Ali, Akbar; Tahir, Muhammad Nawaz; Ahmed, Gulzar; Ramalingam, Arulraj; Alam, Mohammed Mujahid; Imran, Muhammad; Sambandam, Sivakumar; Munir, Budar

doi:10.1007/s13738-021-02432-4

Cited by 26 publications

(13 citation statements)

References 35 publications

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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: 79%

“…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: 87%

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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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Section: Results and Discussionmentioning

confidence: 79%

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confidence: 87%

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

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“…To check the strength of the crystal packing, the void investigation was carried out for PBMP . The calculations were based on some assumptions: all of the atoms are assumed to spherically symmetric and electron densities of all of the atoms are added up to compute the void volume in the crystal packing . Two views of the voids in the crystal packing of PBMP are shown in Figure S3.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

et al. 2022

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Three symmetrical bis-aryl-α,β-unsaturated ketone derivatives, 2,6-di((E)-benzylidene)-cyclohexan-1-one (DBC), 2,6bis((E)-4-chlorobenzylidene)cyclohexan-1-one (BCC), and (1E,1′E,4E,4′E)-5,5′-(1,4-phenylene)bis(2-methyl-1-phenylpenta-1,4-dien-3-one) (PBMP), have been prepared using the aldol condensation approach toward ketones having two enolizable sites. The structures of DBC, BCC, and PBMP have been resolved via spectrometric methods. Moreover, the crystal structure of PBMP is determined by the single-crystal X-ray diffraction (SC-XRD) technique, which revealed that the PBMP molecular assembly is stabilized by the intermolecular C−H•••O bonding and C− O•••π and weak T-shaped offset π•••π stacking interactions. The Hirshfeld surface analysis (HSA) of the PBMP crystal structure was performed as well, and the results were compared with the results of DBC and BCC. The density functional theory (DFT) study results revealed that the longer conjugated molecule of PBMP has smaller but still quite significant HOMO−LUMO gaps compared to the smaller molecules of BCC and DBC.The natural population analysis (NPA) and natural bonding orbital (NBO) analysis were performed. Accordingly, the hydrogen bonding and dipole−dipole interactions stabilize the crystal structures of these compounds. Additionally, the NBO analysis showed numerous high-energy stabilizing interactions for the PBMP compound due to the presence of numerous delocalized and relatively easily polarizable π-electrons, thus implying its significant thermodynamic stability. According to the global reactivity parameter (GRP) analysis, the compounds BCC and DBC are relatively stable in redox processes and have high thermodynamic stability and relatively lower reactivity in general. The molecular electrostatic potential (MEP) analysis results imply potential formation of the intermolecular hydrogen bonding and dispersion interactions, which stabilizes the crystal structures of these compounds.

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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

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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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Single crystal inspection, Hirshfeld surface investigation and DFT study of a novel derivative of 4-fluoroaniline: 4-((4-fluorophenyl)amino)-4-oxobutanoic acid (BFAOB)

Cited by 26 publications

References 35 publications

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

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

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

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

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