Abstract
Historically, the accelerated cycloaddition reactivity of cyclic alkynes relative to acyclic alkynes has been solely attributed to strain and these reactions have been accordingly called strain-promoted azide–alkyne cycloadditions (SPAAC). Based on state-of-the-art quantum chemical analyses, this work shows that, instead, an alternative electronic mechanism can become the decisive factor behind this acceleration, namely: an enhanced orbital interaction that stems from both a destabilization and favorable polarization of the cycloalkyne HOMO towards the azide. More information can be found in the Full Paper by K. N. Houk, F. M. Bickelhaupt, et al. on page 6342.
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