The Radical Cation of Azatriquinane: An ESR Study

Fabian Gerson, Pascal Merstetter, Mark Mascal, Nicholas M. Hext

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6 Scopus citations


Azatriquinane (= 10-azatricyclo[,10]decane; 1) was oxidized to its radical cation 1·+ by γ- irradiation in a CF2ClCFCl2 matrix at 77 K. A prominent feature of the ESR spectrum of 1·+ is the 14N-hyperfine anisotropy which broadens the components with M1(14N)=±1. The observed coupling constants are aN=+2.5 and aH = + 4.0 mT for the 14N nucleus and the three methine β-protons, respectively. While the aN value points to pyramidalization at the N-atom comparable to that in the radical cation of quinuclidine (= 1-azabicyclo[2.2.2]octane; 4), an eclipsing of the singly occupied orbital at this atom by the three C-Hβ bonds is indicated in view of the large aH value. Theoretical calculations on the geometry of 1·+ are in accord with the conclusions drawn from the experimental findings.

Original languageEnglish (US)
Pages (from-to)1749-1753
Number of pages5
JournalHelvetica Chimica Acta
Issue number10
StatePublished - 1998
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)


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