4.8 Article

Shorter Still: Compressing C-C Single Bonds

Journal

ORGANIC LETTERS
Volume 12, Issue 18, Pages 4058-4061

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol101671m

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Funding

  1. Guanajuato by Conacyt [57892]
  2. Richmond by the Research Corporation [7742]
  3. Thomas F. and Kate Miller Jeffress Memorial Trust [J-903]
  4. University of Richmond

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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 angstrom! 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, theta, to minimize strain in the cages and an effort to offset the tension in the surrounding bridges.

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