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Updated: Jul 26, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Tricyclopropylamine and Its Radical Cation
de Meijere A1, Chaplinski, Winsel
1Institut für Organische Chemie der Universität, Tammannstrasse 2, D-37077 Göttingen (Germany).
Abstract:
A surprisingly high first vertical ionization energy (8.44 eV) and an unusually high oxidation potential are exibited by tricyclopropylamine (1)-in sharp contrast to triisopropylamine. These are attributed to the near-tetrahedral geometry of 1 at the N atom and the perpendicular orientation-with respect to the N-orbital axis-of the cyclopropyl groups. gamma-Irradiation of 1 led to the radical cation 1(.)(+), which, in accord with computations, has a planar C(3h)-symmetrical structure. The EPR-spectroscopic and computational results disclose a dramatic, previously not reported, conformational change on going from 1 to 1(.)(+).
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