5,7-Bis(2′-arylethenyl)-6H-1,4-diazepine-2,3-dicarbonitriles: synthesis, and experimental and theoretical evaluation of the effects of substituents at 5,6,7-positions on the molecular configuration and spectral properties
| Autor: | Pavel A. Tarakanov, Victor E. Pushkarev, Larisa G. Tomilova, Vladimir I. Shestov, Alexander V. Dzuban, Anton O. Simakov, Ekaterina N. Tarakanova |
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| Rok vydání: | 2016 |
| Předmět: |
Steric effects
010405 organic chemistry Organic Chemistry Molecular configuration 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Diazepine chemistry Computational chemistry Intramolecular force Diaminomaleonitrile Molecule Aldol condensation Physical and Theoretical Chemistry Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Organic & Biomolecular Chemistry. 14:1138-1146 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c5ob02098k |
| Popis: | A series of novel 5,7-bis(2'-arylethenyl)-6H-1,4-diazepine-2,3-dicarbonitriles was synthesized through sequential aldol condensation reactions of 1,3-diketones with diaminomaleonitrile, and the resulting 5,7-dimethyl-6H-1,4-diazepines were condensed with aromatic aldehydes. The substituents' effects on the spectral properties and conformational states of the molecules in solution were studied using 2D NMR techniques and DFT calculations. Specific intramolecular steric interactions in derivatives substituted at the C6 position were discovered and investigated in detail. Differential scanning calorimetry and thermogravimetric analyses revealed the strong dependence of the thermal stability of the newly prepared diazepinodicarbonitriles on the nature of the substituents. This offers new insight into the structure-property relationships of arylethenyl-substituted diazepine derivatives. |
| Databáze: | OpenAIRE |
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