Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones
- Citation:
- Babjaková, E., L. Dastychová, B. Hanulíková, I. Kuřitka, M. Nečas, H. Vašková, and R. Vícha, "Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones", Journal of Molecular Structure, vol. 1085, pp. 207 - 214, 2015.
Abstract:
Abstract The interest in the oxo-enol tautomerism of 1,3-dioxo compounds is justified by their usefulness in many synthetic fields. A series of new 1,3-bis(1-adamantyl)propan-1,3-diones with a variably substituted phenyl ring at the \{C2\} position was prepared either by the reaction of an appropriate Grignard reagent with adamatane-1-carbonyl chloride or by \{SEAr\} on the unsubstituted 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-dione. In addition to the single crystal X-ray diffraction analysis of three of the prepared compounds, the experimental 1H and 13C NMR, İR\} and Raman spectroscopic data were assigned and compared to those obtained by \{DFT\} computations. In the solid state, the syn-dioxo forms were exclusively observed, which are shown to also predominate in \{CHCl3\} solutions. The analysis of the Hirshfeld surface revealed that H⋯H and O⋯H contacts dominate the intermolecular interactions in the solid state, whereas π⋯π stacking plays a marginal role.
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