Effect of Acceptor and Donor Substituents in the ortho, meta, and para Positions in the Nitrobenzene Molecule on the Reaction of Interaction with Ethylene

Minasyan, Yuri; Degtyarenko, Anastasia I.; Кosmacheva, Karina D.; Плехович, С. Д.; Зеленцов, С. В.

doi:10.3390/ecsoc-22-05770

Cited by 2 publications

(1 citation statement)

References 2 publications

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“…The structure of nitrobenzene has been subject to several modifications, of which the hydrogen atoms of the benzene ring can be substituted either in the ortho, meta, or para position by electrophilic or nucleophilic groups (1). Nitrobenzene and its derivatives have a wide application in industry because they are versatile intermediates in organic synthesis such as the production of aniline and, the synthesis of dyes, pesticides , and rubbers (2-4).…”

Section: Introductionmentioning

confidence: 99%

In-depth Hirschfeld Surface Analysis, Interaction Energy, Molecular Docking, and DFT Investigations of Electronic Properties of 2,4-dimethyl-1-nitrobenzene

Megrouss,

Salem,

Nourdine

et al. 2024

Journal of the Turkish Chemical Society Section A: Chemistry

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Quantum-chemical calculations, molecular docking, and Hirshfeld surface analysis of a structure of 2,4-dimethyl-1-nitrobenzene constitute the main aspects of this work. The crystal structure of the title compound which is liquid at room temperature, was obtained by in situ cryo crystallization The crystal packing is stabilized by C5–H5…O2 and C7–H7C…N1 intermolecular hydrogen bonds. The analysis of the obtained results of the density functional theory calculations is in good agreement with the experimental data. The analysis of global chemical reactivity descriptors shows that the compound exhibits more stability and less reactivity at high polar media. Hirshfeld surface and 2D-fingerprint plots analysis shows that the H…H, O…H/H…O, C…C, and C…H/H…C contacts are the significant contributors stabilizing the crystal structure of 2,4-dimethyl-1-nitrobenzene. The RDG-NCI analysis of the molecule was performed to determine the non-covalent interactions present within the molecule. In addition, the compound under investigation presents a biological activity when it is docked into the protein (PDB ID: 4Y0S) with the binding energy system of -6.6 kcal/mol.

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Section: Introductionmentioning

confidence: 99%

In-depth Hirschfeld Surface Analysis, Interaction Energy, Molecular Docking, and DFT Investigations of Electronic Properties of 2,4-dimethyl-1-nitrobenzene

Megrouss,

Salem,

Nourdine

et al. 2024

Journal of the Turkish Chemical Society Section A: Chemistry

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Insight into Positional Isomerism of N-(Benzo[d]thiazol-2-yl)-o/m/p-Nitrobenzamide: Crystal Structure, Hirshfeld Surface Analysis and Interaction Energy

et al. 2020

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The functionalization of N-(benzo[d]thiazol-2-yl)benzamide with a nitro (NO2) substituent influences the solid-state arrangement, absorption and fluorescence properties of these compounds. Each of these compounds crystallised in a different crystal system or space group, namely a monoclinic crystal system with P21/n and C2/c space groups for o-NO2 and m-NO2 derivatives, respectively, and an orthorhombic crystal system (Pbcn space group) for p-NO2 derivative. The o-NO2 substituent with intrinsic steric hindrance engendered a distorted geometry. Conversely, the m-NO2 derivate displayed the most planar geometry among the analogues. The solid-state architectures of these compounds were dominated by the N−H···N and C−H···O intermolecular hydrogen bonds and were further stabilised by other weak interactions. The dimer synthons of the compounds were established via a pair of N−H···N hydrogen bonds. These findings were corroborated by a Hirshfeld surface analysis and two-dimensional (2D) fingerprint plot. The interaction energies within the crystal packing were calculated (CE-B3LYP/6-31G(d,p)) and the energy frameworks were modelled by CrystalExplorer17.5. The highly distorted o-NO2 congener synthon relied mainly on the dispersion forces, which included π–π interactions compared to the electrostatic attractions found in m-NO2. Besides, the latter possesses an elevated asphericity character, portraying a marked directionality in the crystal array. The electrostatic and dispersion forces were regarded as the dominant factors in stabilising the crystal packing.

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Effect of Acceptor and Donor Substituents in the ortho, meta, and para Positions in the Nitrobenzene Molecule on the Reaction of Interaction with Ethylene

Cited by 2 publications

References 2 publications

In-depth Hirschfeld Surface Analysis, Interaction Energy, Molecular Docking, and DFT Investigations of Electronic Properties of 2,4-dimethyl-1-nitrobenzene

In-depth Hirschfeld Surface Analysis, Interaction Energy, Molecular Docking, and DFT Investigations of Electronic Properties of 2,4-dimethyl-1-nitrobenzene

Insight into Positional Isomerism of N-(Benzo[d]thiazol-2-yl)-o/m/p-Nitrobenzamide: Crystal Structure, Hirshfeld Surface Analysis and Interaction Energy

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