A quantum mechanical Jack in the box: Rapid rearrangement of a tetrahedryl-tetrahedrane via heavy atom tunneling

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Abstract

A bridged tetrahedryl-tetrahedrane (TT) was, theoretically, recognized as the holder of the chemical record for the shortest C-C single bond in a stable molecule. However, owing to its strained nature, this molecule is prone to rearrange to a carbene via ring contraction. Although TT was predicted to be stable to rearrangement at very low temperatures, our calculations find that, due to carbon quantum mechanical tunneling, even at 0 K it will immediately rearrange, with a half-life of only 4 ms. TT provides an excellent example of why tunneling effect should be considered in the stability analysis of a theoretically conceived molecule, even at cryogenic temperatures.

Original languageEnglish
Pages (from-to)4102-4105
Number of pages4
JournalOrganic Letters
Volume16
Issue number16
DOIs
StatePublished - 15 Aug 2014
Externally publishedYes

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