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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
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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. |
format | Online Article Text |
id | pubmed-6002825 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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