التفاصيل البيبلوغرافية
| العنوان: |
Synthesis, crystal structure, hirshfeld surface analysis, spectroscopic, biological and first-principles studies of novel aminocoumarins. |
| المؤلفون: |
Bejaoui, Linda1 (AUTHOR), Brahmia, Ameni1,2 (AUTHOR) ahmiah@kku.edu.sa, Marzouki, Riadh1,2,3,4 (AUTHOR) rmarzouki@kku.edu.sa, Dusek, Michal5 (AUTHOR), Eigner, Vaclav5 (AUTHOR), Serdaroğlu, Goncagül6 (AUTHOR) goncagul.serdaroglu@gmail.com, Kaya, Savaş1,7 (AUTHOR) savaskaya@cumhuriyet.edu.tr, Bour, Monia El8 (AUTHOR), Hassen, Rached Ben1 (AUTHOR) |
| المصدر: |
Journal of Molecular Structure. Dec2020, Vol. 1221, pN.PAG-N.PAG. 1p. |
| مصطلحات موضوعية: |
*SURFACE analysis, *CRYSTAL structure, *INTRAMOLECULAR charge transfer, *APROTIC solvents, *DIMETHYLFORMAMIDE, *FLUORIMETRY |
| مستخلص: |
• The synthesized compounds were characterized by spectroscopic techniques (IR, UV–vis and fluorescence). • Nature of intermolecular contacts C H ••• π and π•••π stacking parallel in the aminocoumarin structures were performed by hirshfeld surface analysis. • NBO analysis was studied for understanding the stability, intramolecular charge transfer and donor-acceptor interactions in the synthesized aminocoumarins. • The fluorescence analysis of aminocoumarins indicates the presence of strong luminescence between 350 nm et 550 nm. • Among the synthesized compounds, compound (1) demonstrated a potent inhibitory effect against the growth of E. coli, V. algino and V.angui strains. Two novel aminocoumarins 3-(1-(2 aminophenylamino) ethylidene)chromene-2,4‑dione, noted (1) and 3-(1-(2–1-(2, 4-dioxochromene-3-ylidene) ethylamino)phenylamino) ethylidene) chromene -2,4‑dione,noted (2), were synthesized from 3-acetyl-4-hydroxycoumarin and ortho-phenylenediamine in absolute ethanol and characterized by spectroscopies methods (FT-IR, UV–vis and fluorescence). The crystal structures of the mentioned compounds were solved from single-crystal diffraction data at low temperature. The compound (1) crystallizes in the orthorhombic system with space group Iba2 while (2) is monoclinic with space group P 2 1 / c. Hirshfeld surface analysis indicates the presence of the π-π stacking in the aminocoumarin structures with the contribution of 7.8% for (1) and 8.7% for (2) of the total Hirshfeld area. The optimized DFT geometries (B3PW91/6–311 G (2df, p)) and the spectral simulations agree well with the experimental data. Theoretical reactivity behavior was assessed, taking into account HOMO-LUMO diagrams and Molecular Electrostatic Potential maps. The two aminocoumarins derivatives have fluorescence properties. Analysis of the photoluminescence spectra shows that the emission intensity is high for the solutions of the two compounds in polar aprotic solvents (DMSO, DMF). The aminocoumarins were monitored for antimicrobial activity using the disk diffusion method. The coumarin (1) is effective against S. aureus (gram-positive bacteria) and S. typhy (gram-negative bacteria), but the coumarin (2) showed markedly weak antibacterial activity. [ABSTRACT FROM AUTHOR] |
| قاعدة البيانات: |
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