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Publication Type : Journal Article
Publisher : Wiley
Source : Journal of Heterocyclic Chemistry, 2021, 58(2), pp. 502–514
Campus : Mysuru
Department : Chemistry
Year : 2021
Abstract : Six α,β-unsaturated carbonyl compounds have been obtained from 2,6-diaryl-3,5-diphenylpiperidine-4-one by the treatment with acetic acid. A plausible mechanism for the ring opening of 2,6-diaryl-3,5-diphenyl piperidin-4-ones is proposed. The resultant (E)-4-aryl-1,3-diphenylbut-3-en-2-ones have been characterized by 1H and 13C nuclear magnetic resonance (NMR) spectral studies. One of the compounds was completely characterized by 2D NMR techniques, and structure of the compound is further proved by single-crystal X-ray diffraction (XRD) analysis. The crystal structure, three-dimensional framework of crystal, and Hirshfeld surface analysis of two of the compounds have been discussed. In the crystals, molecules are mainly linked by CH···O hydrogen bonding interactions, and this interaction forms an inversion dimer with R21(6) and R21(10) ring motifs in one of the compounds. Hirshfeld surface indicates the dominance of H···H contacts on the overall surface.
Cite this Research Publication : Vengatesh, G., Sundaravadivelu, M., Muthusubramanian, S. “Ring opening of 2,6-diaryl-3,5-diphenyl piperidine-4-one by acetic acid: Structural studies and Hirshfeld surface analysis of (E)-4-aryl-1,3-diphenylbut-3-en-2-ones” J. Heterocycl. Chem., 2021, 58(2), pp. 502–514.