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Protonated alcohols are examples of complete charge-shift bonds

Anderson, Peter; Petit, Alban; Ho, Junming; Mitoraj, Mariusz Pawel; Coote, Michelle; Danovich, David; Shaik, Sason; Braida, Benoit; Ess, Daniel H.

Description

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...[Show more]

CollectionsANU Research Publications
Date published: 2014
Type: Journal article
URI: http://hdl.handle.net/1885/63774
Source: Journal of Organic Chemistry
DOI: 10.1021/jo501549q

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