Force-induced retro-click reaction of triazoles competes with adjacent single-bond rupture
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 exte...
Gespeichert in:
| Hauptverfasser: | , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
13 Jun 2017
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| In: |
Chemical science
Year: 2017, Jahrgang: 8, Heft: 8, Pages: 5567-5575 |
| ISSN: | 2041-6539 |
| DOI: | 10.1039/C7SC01562C |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1039/C7SC01562C Verlag, Volltext: https://pubs.rsc.org/en/content/articlelanding/2017/sc/c7sc01562c 
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| Verfasserangaben: | Tim Stauch and Andreas Dreuw |
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| 520 | |a 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. | ||
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