Synthesis of a novel phenytoin derivative: Crystal structure, Hirshfeld surface analysis and DFT calculations

Guerrab, Walid; Lgaz, Hassane; Kansız, Sevgi; Mague, Joel T.; Dege, Necmi; Ansar, Mʼhammed; Marzouki, Riadh; Taoufik, Jamal; Ali, Ismat H.; Ramli, Youssef

doi:10.1016/j.molstruc.2019.127630

Cited by 68 publications

(22 citation statements)

References 59 publications

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“…In addition, this heterocyclic scaffold possess anticorrosion characteristics (El Ouali et al, 2010;Zarrok et al, 2012;Tazouti et al, 2016;El Aoufir et al, 2016;Laabaissi et al, 2019). In a continuation of our recent work focused on the synthesis and biological evaluation of novel heterocyclic compounds (Guerrab et al 2019(Guerrab et al , 2020(Guerrab et al , 2021Abad et al, 2021a,b;Missioui et al 2021) we report here the crystal structure of the title compound (Fig. 1).…”

Section: Chemical Contextmentioning

confidence: 74%

Crystal structure and Hirshfeld surface analysis of 2-(2-oxo-3-phenyl-1,2,3,8a-tetrahydroquinoxalin-1-yl)ethyl acetate

Abad

Ghayati²,

Mubengayi

et al. 2021

Acta Cryst E

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Section: Chemical Contextmentioning

confidence: 74%

Crystal structure and Hirshfeld surface analysis of 2-(2-oxo-3-phenyl-1,2,3,8a-tetrahydroquinoxalin-1-yl)ethyl acetate

Abad

Ghayati²,

Mubengayi

et al. 2021

Acta Cryst E

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“…Chemical hardness and softness were found as, η= 1.2624 eV and S= 0.3960 eV. According to these results, it was determined that the HL molecule has high stability [11,47,48].…”

Section: Frontier Molecular Orbitals (Fmos) Analysis and Global Reactivitymentioning

confidence: 85%

Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2-{(2Z)-2-[1-(4 methoxyphenyl)ethylidene]hydrazinyl}pyridine

Topal

2022

Gazi University Journal of Science

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3-chloro-2-{(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine (HL) was prepared and its structure elucidated by LC/MS-MS, 1H and 13C-NMR, UV-Vis, elemental analysis, FT-Raman and FT-IR. All theoretical calculations and optimized geometry were obtained from the 6-31G(d,p) basis set calculations. Calculated and scaled data of the molecule were compared with the observed FT-Raman and FT-IR spectroscopic data. The theoretical chemical shifts of the HL were performed in chloroform by using the same level with the GIAO method. The UV-Vis analyses of the HL were carried out at three different concentrations in chloroform and ethanol solvents and between 240-440 nm; the calculations of UV-Vis spectra analyses were performed via the TD-DFT method. The charge transfer and hyperconjugative and conjugative interactions were analyzed using the NBO analysis. Furthermore, frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) were also measured using the same method. This work provides a comprehensive electronic properties, vibration analysis and structural information of the title compund.

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“…DFT calculations were carried out with the Gaussian 09 W, and the data were analyzed with various methods [13,14,32–35]. For computational details (including a full list of co‐authors) please refer to the Appendix S1.…”

Section: Methodsmentioning

confidence: 99%

Crystal structure and quantum chemical calculations of (E)1‐benzyl‐3‐((4‐methoxyphenyl)imino)‐5‐methylindolin‐2‐one

El-wahab

Hamdy

Schulzke

et al. 2021

Journal of Heterocyclic Chem

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The known Schiff base compound, (E)1‐benzyl‐3‐((4‐methoxyphenyl)imino)‐5‐methylindolin‐2‐one, was prepared as before by reacting 1‐benzyl‐5‐methylindoline‐2,3‐dione with 4‐methoxyaniline. The product was unambiguously characterized using elemental analysis, 1H and 13C‐NMR spectroscopy, and its new single‐crystal X‐ray structural analysis. Molecular orbital calculations were conducted in order to investigate the structures and relative stabilities of the (E) and (Z) isomers of 1‐benzyl‐3‐([4 methoxyphenyl]‐imino)‐5‐methylindolin‐2‐one. Specific attention was paid to the (E) isomer. The available crystallographic experimental data for the latter ensured also validation of the model structures computationally derived at the theoretical B3LYP/6‐31G(d,p) level.

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Synthesis of a novel phenytoin derivative: Crystal structure, Hirshfeld surface analysis and DFT calculations

Cited by 68 publications

References 59 publications

Crystal structure and Hirshfeld surface analysis of 2-(2-oxo-3-phenyl-1,2,3,8a-tetrahydroquinoxalin-1-yl)ethyl acetate

Crystal structure and Hirshfeld surface analysis of 2-(2-oxo-3-phenyl-1,2,3,8a-tetrahydroquinoxalin-1-yl)ethyl acetate

Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2-{(2Z)-2-[1-(4 methoxyphenyl)ethylidene]hydrazinyl}pyridine

Crystal structure and quantum chemical calculations of (E)1‐benzyl‐3‐((4‐methoxyphenyl)imino)‐5‐methylindolin‐2‐one

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