Advertisement

Very Short C[BOND]C Single Bonds and Their Origin. The Central Bond Length in Bitetrahedryl

Authors

  • Prof. Dr. Paul von Ragué Schlever,

    Corresponding author
    1. Institut fü Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)
    • Institut fü Organische Chemie der Universität Erlangen-Nürnberg Henkestrasse 42, D-8520 Erlangen (FRG)
    Search for more papers by this author
  • Dr. Matthias Bremer

    1. Institut fü Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)
    Search for more papers by this author

  • This work was supported by the Fonds der Chemischen Industrie, the Convex Computer Corporation and ARDEC, Dover, N.J., USA. We thank B. Reindl(Erlangen) for the calculations on 2 and Prof. O. Ermer (Köln) for suggestions.

  • Dedicated to Professor Christoph Rüchardt on the occasion of his 60th birthday

Abstract

A reduced C[BOND]C bond length and a lower rotational barrier: these are apparently the consequences of increasing the H[BOND]C[BOND]C bond angle in ethane according to ab initio calculation. An explanation is thereby provided for the abnormally short central C[BOND]C bond in compounds like bicubyl, in which this bond bears “bent-back” substituents. Since increasing the bond angle causes rehybridization and increased s character in the C[BOND]C bond, it is appropriate to compare the hybridization of the bond in bitetrahedryl (calculated length 1.438 Å) with that of the C[BOND]C single bond in butadiyne (1.384 Å).

Ancillary