5,7-Bis(2’-arylethenyl)-6H-1,4-diazepine-2,3-dicarbonitriles: synthesis, experimental and theoretical evaluation of effect of substituents at 5,6,7-positions on the molecular configuration and spectral properties

Авторы: Tarakanov Pavel A., Simakov Anton O., Dzuban Alexander V., Shestov Vladimir I., Tarakanova Ekaterina N., Pushkarev Victor, Tomilova Larisa G.
Журнал: Organic and Biomolecular Chemistry
Год издания: 2015
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
DOI: 10.1039/C5OB02098K
Аннотация: 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. Substituent 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 C6 position were discovered and investigated in detail. Differential scanning calorimetry and thermogravimetric analysis 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.
Добавил в систему: Дзубан Александр Владимирович

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