The inverted bond in [1.1.1]propellane is a charge-shift bond

Wei Wu; Junjing Gu; Jinshuai Song; Sason Shaik; Philippe C. Hiberty

doi:10.1002/anie.200804965

The inverted bond in [1.1.1]propellane is a charge-shift bond

Wei Wu^*
, Junjing Gu
, Jinshuai Song
, Sason Shaik
, Philippe C. Hiberty

^*Corresponding author for this work

Institute of Chemistry

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

139 Scopus citations

Abstract

Bonded or not bonded? An ab initio valence bond study of [1.1.1]propellane shows that the two bridgehead carbons are linked by a strong and direct σ bond that is neither classically covalent nor classically ionic, but rather a charge-shift bond, in which the covalent-ionic resonance energy plays the major role. As such, the central bond of [1.1.1]propellane closely resembles the single bond of difluorine.

Original language	English
Pages (from-to)	1407-1410
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	8
DOIs	https://doi.org/10.1002/anie.200804965
State	Published - 9 Feb 2009

Keywords

Bond theory
Charge-shift bonds
Propellanes
Valence bond theory

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10.1002/anie.200804965

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abstract = "Bonded or not bonded? An ab initio valence bond study of [1.1.1]propellane shows that the two bridgehead carbons are linked by a strong and direct σ bond that is neither classically covalent nor classically ionic, but rather a charge-shift bond, in which the covalent-ionic resonance energy plays the major role. As such, the central bond of [1.1.1]propellane closely resembles the single bond of difluorine.",

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AU - Wu, Wei

AU - Gu, Junjing

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AU - Shaik, Sason

AU - Hiberty, Philippe C.

PY - 2009/2/9

Y1 - 2009/2/9

N2 - Bonded or not bonded? An ab initio valence bond study of [1.1.1]propellane shows that the two bridgehead carbons are linked by a strong and direct σ bond that is neither classically covalent nor classically ionic, but rather a charge-shift bond, in which the covalent-ionic resonance energy plays the major role. As such, the central bond of [1.1.1]propellane closely resembles the single bond of difluorine.

AB - Bonded or not bonded? An ab initio valence bond study of [1.1.1]propellane shows that the two bridgehead carbons are linked by a strong and direct σ bond that is neither classically covalent nor classically ionic, but rather a charge-shift bond, in which the covalent-ionic resonance energy plays the major role. As such, the central bond of [1.1.1]propellane closely resembles the single bond of difluorine.

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KW - Charge-shift bonds

KW - Propellanes

KW - Valence bond theory

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The inverted bond in [1.1.1]propellane is a charge-shift bond

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Keywords

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