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The ring current in cyclopropane

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Abstract

Mapping of induced current density using the coupled Hartree-Fock “ipsocentric” (CTOCD-DZ/ 6-31G**//RHF/6-31G**) method shows a ring current arising in the σ framework of cyclopropane that is intense, diatropic and annular, and hence is consistent with the numerous literature attributions of σ-aromaticity to this molecule. Localised orbital analysis shows that this current can be attributed to the set of three carbon–carbon bonds. In a similar analysis, the four carbon–carbon bonds of (planar constrained) cyclobutane are found to give rise to a central paratropic current. The maps are consistent with the view that cyclopropane is strongly σ-aromatic, cyclobutane is weakly σ-anti-aromatic, and the larger cycloalkane systems are essentially σ-non-aromatic.

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Authors and Affiliations

  1. Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK

    Patrick W. Fowler & Mark Lillington

  2. Department of Chemistry, University of Arkansas, Fayetteville, Arkansas, 71701, USA

    Jon Baker

Authors
  1. Patrick W. Fowler
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  2. Jon Baker
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  3. Mark Lillington
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Corresponding author

Correspondence to Patrick W. Fowler.

Additional information

Contribution to the Fernando Bernardi Memorial Issue.

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Fowler, P.W., Baker, J. & Lillington, M. The ring current in cyclopropane. Theor Chem Account 118, 123–127 (2007). https://doi.org/10.1007/s00214-007-0253-2

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  • DOI: https://doi.org/10.1007/s00214-007-0253-2

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