Anderson, PeterPetit, AlbanHo, JunmingMitoraj, Mariusz PawelCoote, MichelleDanovich, DavidShaik, SasonBraida, BenoitEss, Daniel H.2015-12-100022-3263http://hdl.handle.net/1885/63774Accurate gas-phase and solution-phase valence bond calculations reveal that protonation of the hydroxyl group of aliphatic alcohols transforms the C-O bond from a principally covalent bond to a complete charge-shift bond with principally "no-bond" character. All bonding in this charge-shift bond is due to resonance between covalent and ionic structures, which is a different bonding mechanism from that of traditional covalent bonds. Until now, charge-shift bonds have been previously identified in inorganic compounds or in exotic organic compounds. This work showcases that charge-shift bonds can occur in common organic species.201410.1021/jo501549q2015-12-10