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Crystal structures of (E)-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenyl-ethyn-yl)cyclo-butane-1,2-di-yl]bis-(pyridin-2-yl-methanone).

ABSTRACT: Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethyl-ene glycol in daylight afforded [3,4-bis-(phenyl-ethyn-yl)cyclo-butane-1,2-di-yl)bis-(pyridin-2-yl-methanone], C32H22N2O2 (3), while (E)-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C17H13NO (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 cyclo-butane ring adopts an rctt conformation.

SUBMITTER: Ushakov IE 

PROVIDER: S-EPMC7001831 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Crystal structures of (<i>E</i>)-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenyl-ethyn-yl)cyclo-butane-1,2-di-yl]bis-(pyridin-2-yl-methanone).

Ushakov Ivan E IE   Odin Ivan S IS   Gloukhov Pavel A PA   Golovanov Alexander A AA   Dorovatovskii Pavel V PV   Vologzhanina Anna V AV  

Acta crystallographica. Section E, Crystallographic communications 20200114 Pt 2

Recrystallization of (<i>E</i>)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethyl-ene glycol in daylight afforded [3,4-bis-(phenyl-ethyn-yl)cyclo-butane-1,2-di-yl)bis-(pyridin-2-yl-methanone], C<sub>32</sub>H<sub>22</sub>N<sub>2</sub>O<sub>2</sub> (<b>3</b>), while (<i>E</i>)-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C<sub>17</sub>H<sub>13</sub>NO (<b>2</b>), remained photoinert. This is the first experimental evidence that pentenynones can be photorea  ...[more]

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