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Force-induced retro-click reaction of triazoles competes with adjacent single-bond rupture

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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.

Graphical abstract: Force-induced retro-click reaction of triazoles competes with adjacent single-bond rupture

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Publication details

The article was received on 07 Apr 2017, accepted on 31 May 2017 and first published on 13 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC01562C
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Force-induced retro-click reaction of triazoles competes with adjacent single-bond rupture

    T. Stauch and A. Dreuw, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC01562C

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