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

Chemical Science
Tim Stauch, Andreas Dreuw

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.

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Citations

Jan 21, 2020·ChemPlusChem·Maria Stratigaki, Robert Göstl
Sep 24, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Lennart Jonathan MierTim Stauch
Nov 11, 2020·Chemistry : a European Journal·Tom BettensFrank De Proft
Mar 23, 2020·Chemical Science·Curtis E ColwellRamesh Jasti
Jan 1, 2021·The Journal of Physical Chemistry. a·Danjo De ChavezJun-Ya Hasegawa
Sep 10, 2020·Journal of the American Chemical Society·Isabel M KleinMaxwell J Robb
Jan 20, 2022·Journal of Chemical Theory and Computation·Josep Maria BofillJordi Ribas-Ariño

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Methods Mentioned

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