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A Competition between Hydrogen, Stacking, and Halogen Bonding in N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach, and DFT Calculation.
Gouda, Mohamed; Ferjani, Hela; Abd El-Lateef, Hany M; Khalaf, Mai M; Shaaban, Saad; Yousef, Tarek A.
  • Gouda M; Department of Chemistry, College of Science, King Faisal University, P.O. Box 380, Al-Ahsa 31982, Saudi Arabia.
  • Ferjani H; Department of Chemistry, College of Science, IMSIU (Imam Mohammad Ibn Saud Islamic University), P.O. Box 5701, Riyadh 11623, Saudi Arabia.
  • Abd El-Lateef HM; Department of Chemistry, College of Science, King Faisal University, P.O. Box 380, Al-Ahsa 31982, Saudi Arabia.
  • Khalaf MM; Chemistry Department, Faculty of Science, Sohag University, P.O. Box 82524, Sohag 82524, Egypt.
  • Shaaban S; Department of Chemistry, College of Science, King Faisal University, P.O. Box 380, Al-Ahsa 31982, Saudi Arabia.
  • Yousef TA; Chemistry Department, Faculty of Science, Sohag University, P.O. Box 82524, Sohag 82524, Egypt.
Int J Mol Sci ; 23(5)2022 Feb 28.
Article in English | MEDLINE | ID: covidwho-1736947
ABSTRACT
N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide (5), C19H15NO3Se, was prepared in two steps from 4,4'-diselanediyldianiline (3) via reduction and subsequent nucleophilic reaction with 2-methyl-3-bromo-1,4-naphthalenedione, followed by acetylation with acetic anhydride. The cytotoxicity was estimated against 158N and 158JP oligodendrocytes and the redox profile was also evaluated using different in vitro assays. The technique of single-crystal X-ray diffraction is used to confirm the structure of compound 5. The enantiopure 5 crystallizes in space group P21 with Flack parameter 0.017 (8), exhibiting a chiral layered absolute structure. Molecular structural studies showed that the crystal structure is foremost stabilized by N-H···O and relatively weak C-H···O contacts between molecules, and additionally stabilized by weak C-H···π and Se···N interactions. Hirshfeld surface analysis is used to quantitatively investigate the noncovalent interactions that stabilize crystal packing. Framework energy diagrams were used to graphically represent the stabilizing interaction energies for crystal packing. The analysis of the energy framework shows that the interactions energies of and C-H···π and C-O···π are primarily dispersive and are the crystal's main important forces. Density functional theory (DFT) calculations were used to determine the compound's stability, chemical reactivity, and other parameters by determining the HOMO-LUMO energy differences. The determination of its optimized surface of the molecular electrostatic potential (MEP) was also carried out. This study was conducted to demonstrate both the electron-rich and electron-poor sites.
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Halogens / Hydrogen Type of study: Experimental Studies Language: English Year: 2022 Document Type: Article Affiliation country: Ijms23052716

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Halogens / Hydrogen Type of study: Experimental Studies Language: English Year: 2022 Document Type: Article Affiliation country: Ijms23052716