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Updated: Jan 5, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
In search of Coulson's lost theorem
Patrick W Fowler1, Barry T Pickup1
1Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom.
Abstract:
In Hückel theory, the bond number is the sum of the orders of the π bonds incident on a given carbon center. From the work of Coulson and his school, it has been believed for over 70 years that the bond number has a maximum of 3 and that this bound is realized by exactly one conjugated framework, that of the trimethylenemethane radical. Search of published literature and archived correspondence failed to find any formal proof of these two statements. Here, we provide a new formula for bond number that leads to an easily checked proof of both. The bond number of graphene is 1.574 597… (90.9% of the mathematical limit), and this value appears to act as a separator for the classes of metallic and semiconducting single-walled nanotubes, as defined within Hückel theory.
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