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.

Mohamed Gouda,Hela Ferjani,Saad Shaaban,Mai M Khalaf,Tarek A Yousef,Hany M Abd El-Lateef

doi:10.3390/ijms23052716

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.

Highlights

Selenium (Se) is a substantial micronutrient pivotal for the normal function of the human body [1–4]
The 4,40 -Diselanediyldianiline (3) was used for the synthesis of diverse organoselenium compounds by the reduction of the diselenide bond followed by a nucleophilic reaction with different halogenated compounds
The structure of the novel organoselenium compound 5 was confirmed through employing the single-crystal X-ray diffraction technique

Summary

Introduction

Selenium (Se) is a substantial micronutrient pivotal for the normal function of the human body [1–4]. It is found in foods (e.g., tuna, sardines beans, spinach, Brazil nuts) as well as in the structure of different proteins, i.e., selenoproteins [3,4]. Several key enzymes possess core Se responsible for their interesting redox potential, such as the glutathione peroxidase (GPx) and thioredoxin reductases (TrxR) [27–29]. Within this context, organoselenium compounds mimicking the GPx showed interesting antioxidant, anti-inflammatory, and antitumor activities [27,29–32]

Methods

Results

Conclusion