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Open Access Synthesis and crystal structure of methyl 3-(3-hydroxy-3-phenylprop-2-enoyl)benzoate

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The title compound, C17H14O4, 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 intramolecular ...O=C—C=C—OH... hydrogen bond is present in the molecular 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 molecules are assembled through numerous C—H...π and π–π as well as weak C(aryl)—H...O interactions, thus forming a dense crystal packing. The obtained substance was also studied by UV–Vis spectroscopy and cyclic voltammetry.
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Document Type: Research Article

Affiliations: 1: Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills 1/3, Moscow 119991, Russian Federation 2: Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskiy pr. 31, Moscow 119991, Russian Federation

Publication date: January 1, 2018

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