Anderson Peter, Petit Alban, Ho Junming, Mitoraj Mariusz Pawel, Coote Michelle L, Danovich David, Shaik Sason, Braïda Benoît, Ess Daniel H
Department of Chemistry and Biochemistry, Brigham Young University , Provo, Utah 84602, United States.
J Org Chem. 2014 Nov 7;79(21):9998-10001. doi: 10.1021/jo501549q. Epub 2014 Oct 15.
Accurate 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.
