Synthesis, Crystallographic and Spectral Studies of 3-(4-(Phenylamino) Phenylamino)Cyclohex-2-Enone

Abstract

AbstractThe title compound, 3-(4-(phenylamino)phenylamino)cyclohex-2-enone, β-enaminone of 1,3-cyclohexanedione and p-amino diphenylamine (C 18 H 18 N 2 O) was prepared and characterized by 1 H-NMR, 13 C-NMR, Elemental analysis and IR spectroscopy as well as single crystal X-ray diffraction. These results indicate the predominance of the keto-enol tautomerism. Molecular conformation around the central disubstituted benzene ring is affected by the tautomerism and two steric effects between side molecular groups and mono substituted benzene ring. Electron delocalizations due to these effects have been observed in the molecular structure, the structure being stabilized by some intermolecular hydrogen bonds.Graphical AbstractThe title compound, 3-(4-(phenylamino)phenylamino)cyclohex-2-enone, was synthesized by the treatment of 1,3-cyclohexanedione with p-amino diphenylamine and its crystal structure determined. According to 1 H and 13 C NMR data the newly prepared β-enaminone compound exists as the E-s-E-s-Z conformation. This is consistent with X-ray crystallographic study. [IMAGE]