Protonated alcohols are examples of complete charge-shift bonds

Peter Anderson; Alban Petit; Junming Ho; Mariusz Pawel Mitoraj; Michelle L. Coote; David Danovich; Sason Shaik; Benoît Braïda; Daniel H. Ess

doi:10.1021/jo501549q

Protonated alcohols are examples of complete charge-shift bonds

Peter Anderson, Alban Petit, Junming Ho, Mariusz Pawel Mitoraj, Michelle L. Coote, David Danovich, Sason Shaik, Benoît Braïda^*, Daniel H. Ess

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

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.

Original language	English
Pages (from-to)	9998-10001
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	79
Issue number	21
DOIs	https://doi.org/10.1021/jo501549q
Publication status	Published - 7 Nov 2014

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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.",

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AU - Anderson, Peter

AU - Petit, Alban

AU - Ho, Junming

AU - Mitoraj, Mariusz Pawel

AU - Coote, Michelle L.

AU - Danovich, David

AU - Shaik, Sason

AU - Braïda, Benoît

AU - Ess, Daniel H.

PY - 2014/11/7

Y1 - 2014/11/7

N2 - 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.

AB - 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.

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U2 - 10.1021/jo501549q

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VL - 79

SP - 9998

EP - 10001

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Protonated alcohols are examples of complete charge-shift bonds

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