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Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone)
Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethylene glycol in daylight afforded [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl)bis(pyridin-2-ylmethanone], C(32)H(22)N(2)O(2) (3), while (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7001831/ https://www.ncbi.nlm.nih.gov/pubmed/32071745 http://dx.doi.org/10.1107/S2056989020000055 |
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author | Ushakov, Ivan E. Odin, Ivan S. Gloukhov, Pavel A. Golovanov, Alexander A. Dorovatovskii, Pavel V. Vologzhanina, Anna V. |
author_facet | Ushakov, Ivan E. Odin, Ivan S. Gloukhov, Pavel A. Golovanov, Alexander A. Dorovatovskii, Pavel V. Vologzhanina, Anna V. |
author_sort | Ushakov, Ivan E. |
collection | PubMed |
description | Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethylene glycol in daylight afforded [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl)bis(pyridin-2-ylmethanone], C(32)H(22)N(2)O(2) (3), while (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C(17)H(13)NO (2), remained photoinert. This is the first experimental evidence that pentenynones can be photoreactive when fixed in nearly coplanar parallel positions. During the photoreaction, the bond lengths and angles along the pentenyne chain changed significantly, while the disposition of the pyridyl ring towards the keto group was almost unchanged. The cyclobutane ring adopts an rctt conformation. |
format | Online Article Text |
id | pubmed-7001831 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-70018312020-02-18 Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) Ushakov, Ivan E. Odin, Ivan S. Gloukhov, Pavel A. Golovanov, Alexander A. Dorovatovskii, Pavel V. Vologzhanina, Anna V. Acta Crystallogr E Crystallogr Commun Research Communications Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethylene glycol in daylight afforded [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl)bis(pyridin-2-ylmethanone], C(32)H(22)N(2)O(2) (3), while (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C(17)H(13)NO (2), remained photoinert. This is the first experimental evidence that pentenynones can be photoreactive when fixed in nearly coplanar parallel positions. During the photoreaction, the bond lengths and angles along the pentenyne chain changed significantly, while the disposition of the pyridyl ring towards the keto group was almost unchanged. The cyclobutane ring adopts an rctt conformation. International Union of Crystallography 2020-01-14 /pmc/articles/PMC7001831/ /pubmed/32071745 http://dx.doi.org/10.1107/S2056989020000055 Text en © Ushakov et al. 2020 http://creativecommons.org/licenses/by/4.0/ 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/4.0/ |
spellingShingle | Research Communications Ushakov, Ivan E. Odin, Ivan S. Gloukhov, Pavel A. Golovanov, Alexander A. Dorovatovskii, Pavel V. Vologzhanina, Anna V. Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
title | Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
title_full | Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
title_fullStr | Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
title_full_unstemmed | Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
title_short | Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
title_sort | crystal structures of (e)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone) |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7001831/ https://www.ncbi.nlm.nih.gov/pubmed/32071745 http://dx.doi.org/10.1107/S2056989020000055 |
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