title: Protonated alcohols are examples of complete charge-shift bonds.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University , Provo, Utah 84602, United States.
authors.forename: Peter
authors.initials: P
authors.lastname: Anderson
authors.forename: Alban
authors.initials: A
authors.lastname: Petit
authors.forename: Junming
authors.initials: J
authors.lastname: Ho
authors.forename: Mariusz Pawel
authors.initials: MP
authors.lastname: Mitoraj
authors.forename: Michelle L
authors.initials: ML
authors.lastname: Coote
authors.forename: David
authors.initials: D
authors.lastname: Danovich
authors.forename: Sason
authors.initials: S
authors.lastname: Shaik
authors.forename: Benoît
authors.initials: B
authors.lastname: Braïda
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Ess
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D004579:Electron Transport; D006860:Hydrogen Bonding; D007287:Inorganic Chemicals; D007477:Ions / Q000737:chemistry*; D008958:Models, Molecular; D055601:Organic Chemistry Phenomena; D011522:Protons
chemical_list: D000438:Alcohols; D007287:Inorganic Chemicals; D007477:Ions; D011522:Protons