Inverted Hyperconjugation in Symmetrical 1, 4??Dihalocubanes

E Honegger, E Heilbronner, T Urbanek…

Index: Honegger, Evi; Heilbronner, Edgar; Urbanek, Thomas; Martin, Hans-Dieter Helvetica Chimica Acta, 1985 , vol. 68, p. 23 - 38

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Citation Number: 16

Abstract

Abstract The σ-orbital manifold of cubane 1, as suggested by its PE spectrum, is divided into two sets separated by a 3 eV gap extending from∼-10.5 eV to∼-13.5 eV. Halogen substituents with np AO basis energies falling into this gap (eg Cl or Br) will, therefore, hyperconjugate appreciably with both sets. Interaction with the lower-lying set will lead to the usual destabilization ('normal'hyperconjugation), whereas interaction with the set above ...