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. Issue 3 (8th December 2015)

• Record Type: Journal Article
• Authors: Tarakanov, Pavel A.; Simakov, Anton O.; Dzuban, Alexander V.; Shestov, Vladimir I.; Tarakanova, Ekaterina N.; Pushkarev, Victor E.; Tomilova, Larisa G.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 3(2016)
• Page Start: 1138
• Page End: 1146
• Publication Date: 2015-12-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02098k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Synthetic and conformational studies are reported. Abstract : A series of novel 5, 7-bis(2′-arylethenyl)-6 H -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-6 H -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.