Synthesis and crystal structure of methyl 3-(3-hy-droxy-3-phenyl-prop-2-eno-yl)benzoate

The title compound, C H O , was synthesized under mild conditions and characterized by various analytical techniques. Combined NMR and X-ray diffraction data show that the substance exists exclusively in the enol tautomeric form. An intra-molecular ⋯O=C-C=C-OH⋯ hydrogen bond is present in the mol-ec...

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Published inActa crystallographica. Section E, Crystallographic communications Vol. 74; no. Pt 6; pp. 816 - 819
Main Authors Zharinova, Irina S, Bilyalova, Alfiya A, Bezzubov, Stanislav I
Format Journal Article
LanguageEnglish
Published England International Union of Crystallography 01.06.2018
Subjects
crystal structure
hydrogen bond
Research Communications
tautomerism
β-diketone
tautomerism
crystal structure
β-diketone
hydrogen bond
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Summary:The title compound, C H O , was synthesized under mild conditions and characterized by various analytical techniques. Combined NMR and X-ray diffraction data show that the substance exists exclusively in the enol tautomeric form. An intra-molecular ⋯O=C-C=C-OH⋯ hydrogen bond is present in the mol-ecular structure. The analysis of the difference density map disclosed two adjacent positions of a disordered hydrogen atom taking part in this hydrogen bond, indicating the presence of two enol tautomers in the crystal. The enol mol-ecules are assembled through numerous C-H⋯π and π-π as well as weak C(ar-yl)-H⋯O inter-actions, thus forming a dense crystal packing. The obtained substance was also studied by UV-Vis spectroscopy and cyclic voltammetry.
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ISSN:2056-9890
2056-9890
DOI:10.1107/S2056989018007259