Crystal structure and spectral of new hydrazine-pyran-dione derivative: DFT enol↔hydrazone tautomerization via zwitterionic intermediate, hirshfeld analysis and optical activity studies
| Autor: | Abdenour Guerraoui, Ali Alsalme, Abdelkader Zarrouk, Abdecharif Boumaza, Kifah S. M. Salih, Amel Djedouani, Ismail Warad, Erwann Jeanneau |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Schiff base 010405 organic chemistry Hydrogen bond Hirshfeld surface Organic Chemistry Hydrazone DFT calculations 010402 general chemistry 01 natural sciences Enol Tautomer 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Crystallography chemistry Enol↔hydrazinium Pyran Intramolecular force Crystal structures Optical Spectroscopy Derivative (chemistry) |
| Zdroj: | Journal of Molecular Structure. 1220:128728 |
| ISSN: | 0022-2860 |
| Popis: | A novel functionalized Schiff base derivative, (E)-3-(1-(2-(9H-fluoren-9-ylidene)hydrazineyl)ethylidene)-6-methyl-2H-pyran-2,4(3H)-dione, was synthesized via subsequent condensation/tautomerization processes in a high yield. The product was fully characterized using NMR, FT-IR, and single-crystal XRD; the results of DFT simulations were in respectable agreement with crystallographic data. To elucidate the isomerization, the enol↔hydrazinium tautomerism has been pursued theoretically, suggesting an intramolecular single proton transfer (SPT) from enol (O ….H) to the closest NC unit, giving the hydrazine (N–H) via [N+—H ….O−] S (6) zwitterionic intermediate. The results of Hirshfeld surface analysis (HSA) and Molecular electronic potential (MEP) were matching the experimental XRD results. Since a number of hydrogen bonding groups, C–H …. π, and π …. π-stacking interactions were detected experimentally. The optical properties of the desired compound were experimentally and theoretically figure out. The authors acknowledge the Algerian Directorate General for Scientific Research and Technological Development and the Algerian Ministry of Higher Education and Scientific Research, for support of this work. Researchers Supporting Project (RSP-2020/78), King Saud University, Riyadh, Saudi Arabia. |
| Databáze: | OpenAIRE |
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