Steric Crowding Can Stabilize a Labile Molecule: Solving the Hexaphenylethane Riddle
- 24 October 2011
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 50 (52) , 12639-12642
Abstract
12 not so angry men: Hexaphenylethane is unstable, a phenomenon traditionally attributed to steric repulsion between the six phenyl rings. However, adding 12 bulky tert-butyl groups, one to each of the 12 meta positions, gives a stabile ethane derivative (see space-filling model and potential energy curve for the dissociation of the central CC bond). This unexpected stabilization is shown to result from attractive dispersion interactions between the substituents.Keywords
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