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The instability of the planar structure of carbanion ⊖:CH2-CN

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Abstract

Ab initio SCF calculations using uniform quality extended basis set supplemented with polarization functions predict a slightly pyramidal carbanion centre in ⊖:CH2-C≡N. This finding is in contrast to the usual finding of planar geometry of carbanion centres generated next to other conjugative groups. Although the predicted barrier to pyramidal inversion is very small (∼0.1 kcal/mole) it is estimated that correlation energy contributions, neglected in any SCF calculations, may be too small to remove the barrier. The present results confirm earlier experimental findings that counter-ion and solvent effects can have a dominant role in determining the geometry of this unusual ion in actual chemical systems.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, University of Saskatchewan, S7N 0W0, Saskatoon, Saskatchewan, Canada

    Paul G. Mezey

  2. Department of Chemistry, Queen Elizabeth College, University of London, London, England

    Michael A. Robb

  3. Department of Chemistry, University of Toronto, 80 St. George Street, M5S 1A1, Toronto, Ontario, Canada

    Keith Yates & Imre G. Csizmadia

Authors
  1. Paul G. Mezey
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  2. Michael A. Robb
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  3. Keith Yates
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  4. Imre G. Csizmadia
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Mezey, P.G., Robb, M.A., Yates, K. et al. The instability of the planar structure of carbanion ⊖:CH2-CN. Theoret. Chim. Acta 49, 277–281 (1978). https://doi.org/10.1007/BF00550037

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  • DOI: https://doi.org/10.1007/BF00550037

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