Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, European Journal of Organic Chemistry called Molecular Structure, Intramolecular Hydrogen Bonding, Solvent-Induced Isomerization, and Tautomerism in Azolylmethylidene Derivatives of 2-Indanone, Author is Sigalov, Mark V.; Shainyan, Bagrat A.; Chipanina, Nina N.; Oznobikhina, Larisa P., which mentions a compound: 948552-36-1, SMILESS is O=CC1=CC=NN1, Molecular C4H4N2O, Application of 948552-36-1.
Bis adducts of 2-indanone with 1H-pyrrole-2-carbaldehyde, 1H-imidazole-2-carbaldehyde, 1H-imidazole-5-carbaldehyde, and 1H-indazole-3-carbaldehyde 3-6 were synthesized and the intertwined processes of tautomeric NH proton transfer, intra- and intermol. H-bond rupture and formation, and Z/Z, Z/E, and E/E-isomerization were studied by NMR and FTIR spectroscopy and by conducting DFT calculations Pyrrole derivative 3 both in chloroform and in DMSO exists exclusively as the Z,Z-isomer stabilized by two intramol. N-H···O hydrogen bonds. For derivatives 4-6, the isomeric composition depends on the solvent so that in polar media such as DMSO and pyridine the Z,E- and E,E-isomers predominate. The driving force for isomerization of 4-6 is stabilization of the Z,E- and E,E-isomers in basic polar solvents due to formation of intermol. NH···B and intramol. C-H···N hydrogen bonds. The suggested mechanism of isomerization includes proton transfer from nitrogen to oxygen in the Z-moiety followed by rotation about the C-C bond in the formed enol and isomerization of the latter to the E-moiety of the ketone tautomer.
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