Conformational variability in a new terpenoid-like bischalcone: Structure and theoretical studies

Fernandes, W. B.; Malaspina, L. A.; Martins, F. T.; Lião, L. M.; Camargo, A. J.; Lariucci, C.; Noda-Perez, C.; Napolitano, H. B. (2013). Conformational variability in a new terpenoid-like bischalcone: Structure and theoretical studies. Journal of Structural Chemistry, 54(6), pp. 1112-1121. Springer 10.1134/S0022476613060164

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A new terpenoid-like bischalcone (1E,4E)-1-(4-nitrophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)-penta-1,4-dien-3-one was synthesized from a β-ionone and 4-nitrobenzaldehyde by Claisen-Schmidt condensation reaction and its structure was determined by single crystal X-ray diffraction analysis. Additionally, this compound was featured by powder X-ray diffraction, 1H, 13C NMR and IR spectroscopy techniques. The molecule in the asymmetric unit showed disordered occupancy sites over two positions for the trimethylcyclohexene atoms. These two conformations were related by a rotation of about 180° around the axis of the C-C bond linking the six-membered ring and the olefin carbons. Single-molecule calculations using the DFT method have strengthened this structural finding, since our theoretical approaches also suggest two well-defined conformations of similar energies which resemble the molecular geometries determined by X-ray diffraction. Furthermore, the inspection of the crystal packing revealed that the hydrogen bonding patterns are different for each conformation of the compound reported here.

Item Type:

Journal Article (Original Article)


08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Malaspina, Lorraine


500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry








Simon Grabowsky

Date Deposited:

18 May 2021 10:27

Last Modified:

18 May 2021 10:27

Publisher DOI:





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