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The Inverted Bond in [1.1.1]Propellane is a Charge-Shift Bond†

  1. Wei Wu Prof.1,
  2. Junjing Gu1,
  3. Jinshuai Song1,
  4. Sason Shaik Prof.2,
  5. Philippe C. Hiberty Prof.3

Article first published online: 15 DEC 2008

DOI: 10.1002/anie.200804965

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 8, pages 1407–1410, February 9, 2009

Additional Information

How to Cite

Wu, W., Gu, J., Song, J., Shaik, S. and Hiberty, Philippe C. (2009), The Inverted Bond in [1.1.1]Propellane is a Charge-Shift Bond. Angew. Chem. Int. Ed., 48: 1407–1410. doi: 10.1002/anie.200804965

Author Information

  1. 1

    State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005 (P.R. China), Fax: (+86) 592-218-4708

  2. 2

    Institute of Chemistry and The Lise Meitner-Minerva Center for Computational Quantum Chemistry, The Hebrew University, Jerusalem, 91904 (Israel), Fax: (+972) 2-658-4680

  3. 3

    Laboratoire de Chimie Physique, Groupe de Chimie Théorique, CNRS UMR 8000, Université de Paris-Sud, 91405 Orsay Cédex (France), Fax: (+33) 1-6941-6175

  1. †

    The research in Xiamen is supported by the Natural Science Foundation of China (No 20533020, 20873106) and the National Basic Research Program of China (204CB719902). S.S. is supported by an ISF grant (16/06)

Publication History

  1. Issue published online: 30 JAN 2009
  2. Article first published online: 15 DEC 2008
  3. Manuscript Received: 10 OCT 2008

Funded by

  • Natural Science Foundation of China. Grant Numbers: 20533020, 20873106
  • National Basic Research Program of China. Grant Number: 204CB719902

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Keywords:

  • bond theory;
  • charge-shift bonds;
  • propellanes;
  • valence bond theory

Abstract

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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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