Syntheses and X-ray crystal structures combined with conformational and Hirshfeld analyses of chalcones based on a cyclohexanone scaffold
| Autor: | Gehad Lotfy, Yasmine M. Abdel Aziz, Mohamed M. Said, Assem Barakat, Abdullah Mohammed Al-Majid, El Sayed H. El Ashry, El Sayed H. El Tamany, Saied M. Soliman, Hazem A. Ghabbour |
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| Rok vydání: | 2019 |
| Předmět: |
Steric effects
010405 organic chemistry Chemistry Organic Chemistry Cyclohexanone Crystal structure 010402 general chemistry Ring (chemistry) 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Crystallography Intramolecular force Orthorhombic crystal system Spectroscopy Basis set Monoclinic crystal system |
| Zdroj: | Journal of Molecular Structure. 1198:126873 |
| ISSN: | 0022-2860 |
| Popis: | Four chalcone structures based on cyclohexanone cores were presented. The structures of bis-benzylidenecyclohexanone analogs 3a-d were elucidated using spectrophotometric and single-crystal X-ray techniques. Compounds 3a, 3b, and 3d crystalized in the monoclinic crystal system with the space group P21/c. However, 3c crystalized in the orthorhombic system with the space group Pna21. A set of computational studies related to the structures were carried out. Using the B3LYP method and the 6-31G(d,p) basis set, the molecular structures of the studied dienones were optimized, followed by the evaluation of their electronic properties and UV–vis spectra. The bond distances and angles well-correlated with the experimental data. All the dienones were stabilized by C–H⋯O intramolecular H-bonding interactions. The presence of two Cl atoms at the ortho-position of each phenyl ring in 3c caused steric hinderance with the cyclohexanone ring, leading to the weakest H⋯O interactions among the studied compounds. The TD-DFT method was used to assign and explain the origin of the electronic spectra of the studied dienones. |
| Databáze: | OpenAIRE |
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