How short can a C-C single bond get? The bonding in a set of molecules that are related structurally to previously synthesized or theoretically examined systems with short C-C bonds is investigated. According to calculations, a single C-C bond could be compressed to 1.313 A! To the best of our knowledge, this is the shortest single C-C bond reported to date. This shortening is a consequence of a change in the C-C-C bond angle, θ, to minimize strain in the cages and an effort to offset the tension in the surrounding bridges.
Copyright © 2010 American Chemical Society. This article first appeared in Organic Letters 12:18 (2010), 4058-4061.
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Martinez-Guajardo, Gerardo, Kelling J. Donald, Bernard K. Wittmaack, Miguel Angel Vazquez, and Gabriel Merino. "Shorter Still: Compressing C-C Single Bonds." Organic Letters 12, no. 18 (2010): 4058-4061. doi:10.1021/ol101671m.