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The Inverted Bond in [1.1.1]Propellane is a Charge‐Shift Bond
Author(s) -
Wu Wei,
Gu Junjing,
Song Jinshuai,
Shaik Sason,
Hiberty Philippe C.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804965
Subject(s) - propellane , covalent bond , chemistry , ionic bonding , single bond , valence bond theory , bond order , pi bond , computational chemistry , bond length , crystallography , stereochemistry , molecule , bicyclic molecule , molecular orbital , alkyl , organic chemistry , crystal structure , ion
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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