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

The title compound, C(17)H(14)O(4), 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 th...

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Autores principales: Zharinova, Irina S., Bilyalova, Alfiya A., Bezzubov, Stanislav I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6002825/
https://www.ncbi.nlm.nih.gov/pubmed/29951237
http://dx.doi.org/10.1107/S2056989018007259
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author Zharinova, Irina S.
Bilyalova, Alfiya A.
Bezzubov, Stanislav I.
author_facet Zharinova, Irina S.
Bilyalova, Alfiya A.
Bezzubov, Stanislav I.
author_sort Zharinova, Irina S.
collection PubMed
description The title compound, C(17)H(14)O(4), 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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spelling pubmed-60028252018-06-27 Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate Zharinova, Irina S. Bilyalova, Alfiya A. Bezzubov, Stanislav I. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(17)H(14)O(4), 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. International Union of Crystallography 2018-05-18 /pmc/articles/PMC6002825/ /pubmed/29951237 http://dx.doi.org/10.1107/S2056989018007259 Text en © Zharinova et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Zharinova, Irina S.
Bilyalova, Alfiya A.
Bezzubov, Stanislav I.
Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
title Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
title_full Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
title_fullStr Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
title_full_unstemmed Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
title_short Synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
title_sort synthesis and crystal structure of methyl 3-(3-hy­droxy-3-phenyl­prop-2-eno­yl)benzoate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6002825/
https://www.ncbi.nlm.nih.gov/pubmed/29951237
http://dx.doi.org/10.1107/S2056989018007259
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