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Protonated alcohols are examples of complete charge-shift bonds

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dc.contributor.authorAnderson, Peter
dc.contributor.authorPetit, Alban
dc.contributor.authorHo, Junming
dc.contributor.authorMitoraj, Mariusz Pawel
dc.contributor.authorCoote, Michelle
dc.contributor.authorDanovich, David
dc.contributor.authorShaik, Sason
dc.contributor.authorBraida, Benoit
dc.contributor.authorEss, Daniel H.
dc.date.accessioned2015-12-10T23:11:20Z
dc.date.issued2014
dc.date.updated2015-12-10T09:21:42Z
dc.description.abstractAccurate 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.
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/63774
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleProtonated alcohols are examples of complete charge-shift bonds
dc.typeJournal article
local.bibliographicCitation.issue21
local.bibliographicCitation.lastpage10001
local.bibliographicCitation.startpage9998
local.contributor.affiliationAnderson, Peter, Brigham Young University
local.contributor.affiliationPetit, Alban, Brigham Young University
local.contributor.affiliationHo, Junming, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMitoraj, Mariusz Pawel, Jagiellonian University
local.contributor.affiliationCoote, Michelle, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationDanovich, David, The Hebrew University of Jerusalem
local.contributor.affiliationShaik, Sason, The Hebrew University of Jerusalem
local.contributor.affiliationBraida, Benoit, Sorbonne Universités
local.contributor.affiliationEss, Daniel H., Brigham Young University
local.contributor.authoruidHo, Junming, u4041618
local.contributor.authoruidCoote, Michelle, u4031074
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030701 - Quantum Chemistry
local.identifier.absfor030505 - Physical Organic Chemistry
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu4005981xPUB846
local.identifier.citationvolume79
local.identifier.doi10.1021/jo501549q
local.identifier.scopusID2-s2.0-84909990978
local.identifier.thomsonID000344638200009
local.type.statusPublished Version

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