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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...

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Autores principales: Ushakov, Ivan E., Odin, Ivan S., Gloukhov, Pavel A., Golovanov, Alexander A., Dorovatovskii, Pavel V., Vologzhanina, Anna V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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