Investigation of Hyperconjugation by UV-Photoelectron Spectroscopy

  • Author: ChemPlusChem
  • Published Date: 17 April 2013
  • Source / Publisher: ChemPlusChem/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Investigation of Hyperconjugation by UV-Photoelectron Spectroscopy

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In organic chemistry, hyperconjugation is responsible for a variety of phenomena, including the anomeric effect, gauche effect, β-silicon effect, stability of carbocations and free radicals.

To visualize the effects of hyperconjugation, Akira Sekiguchi, University of Tsukuba, Japan, and colleagues synthesized tetrakis(trimethylsilyl)tetrahedrane 1 and its pentafluorophenyl derivative 2 and recorded their ultraviolet photoelectron spectra (UV-PES).

The observation of an energy gap of 2.0 eV between the first and fourth ionization bands of 2 provides clear-cut evidence for the σtetrahedraneπarene orbital interaction (neutral hyperconjugation). This nicely supports the preliminarily proposed neutral hyperconjugation in 2, which was based on structural and spectroscopic data.

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Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH