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Thomas Scattolin1, Enrica Bortolamiol2, Stefano Palazzolo3

  • 1Department of Chemistry and Center for Sustainable Chemistry, Ghent University, Krijgslaan 281 (S-3), Ghent, 9000, Belgium.

Chemical Communications (Cambridge, England)
|September 14, 2020
PubMed

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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...