Re‐establishing the Lost Covalency of the Inverted Bond in [1.1.1]Propellane

The nature of the bridging C−C bond in [1.1.1]propellane has been a topic of much debate, and finally it has been established to be a charge‐shift bond. But the question remains: Can we restore the “lost” covalency of this charge shift bond? Herein we have attempted to investigate the nature of the...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2023-08, Vol.8 (29), p.n/a
Main Authors: Sultana, Nargish, Guha, Ankur Kanti
Format: Article
Language:English
Subjects:
AIM
Charge-shift
Chemical Bond
ELF
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Summary:The nature of the bridging C−C bond in [1.1.1]propellane has been a topic of much debate, and finally it has been established to be a charge‐shift bond. But the question remains: Can we restore the “lost” covalency of this charge shift bond? Herein we have attempted to investigate the nature of the bridging C−C bond, by replacing the CH2 groups at the wing positions with NH, O, and S. Detailed analyses using atoms in molecules (AIM) and electron localization function (ELF) reveal that the bridging bond emerges as a covalent bond upon substitution with S. Electron density analysis reveals that S atom at the wings of [1.1.1]propellane derivative re‐establishes the lost covalency of the inverted central bridge C−C bond.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202302714