Status: Bibliographieeintrag
Standort: ---
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| Online-Ressource |
Verfasst von: | Stauch, Tim [VerfasserIn]  |
| Dreuw, Andreas [VerfasserIn]  |
Titel: | Force-induced retro-click reaction of triazoles competes with adjacent single-bond rupture |
Verf.angabe: | Tim Stauch and Andreas Dreuw |
Umfang: | 9 S. |
Fussnoten: | Gesehen am 14.09.2018 |
Titel Quelle: | Enthalten in: Chemical science |
Jahr Quelle: | 2017 |
Band/Heft Quelle: | 8(2017), 8, S. 5567-5575 |
ISSN Quelle: | 2041-6539 |
Abstract: | The highly controversial force-induced cycloreversion of 1,2,3-triazole, its well-known retro-click reaction, is shown to be possible only for 1,5-substituted triazoles, but competes with rupture of an adjacent single-bond. We draw this conclusion from both static and dynamic calculations under external mechanical forces applied to unsubstituted and 1,4- and 1,5-substituted triazoles. The JEDI (Judgement of Energy DIstribution) analysis, a quantum chemical tool quantifying the distribution of strain energy in mechanically deformed molecules, is employed to identify the key factors facilitating the force-induced retro-click reaction in these systems. For 1,4-substituted triazoles it is shown to be impossible, but the parallel alignment of the scissile bond in 1,5-substituted triazoles with the acting force makes it generally feasible. However, the weakness of the carbon-nitrogen bond connecting the triazole ring to the linker prevents selective cycloreversion. |
DOI: | doi:10.1039/C7SC01562C |
URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Verlag: http://dx.doi.org/10.1039/C7SC01562C |
| Verlag: https://pubs.rsc.org/en/content/articlelanding/2017/sc/c7sc01562c |
| DOI: https://doi.org/10.1039/C7SC01562C |
Datenträger: | Online-Ressource |
Sprache: | eng |
K10plus-PPN: | 1580976425 |
Verknüpfungen: | → Zeitschrift |
Force-induced retro-click reaction of triazoles competes with adjacent single-bond rupture / Stauch, Tim [VerfasserIn] (Online-Ressource)
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