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Updated: Jun 3, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Triplet ground state derivative of aza-m-xylylene diradical with large singlet-triplet energy gap
Andrzej Rajca1, Arnon Olankitwanit, Suchada Rajca
1Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, USA. arajca1@unl.edu
Abstract:
Organic molecules with a strong preference for triplet ground states, in which the triplet state is below the lowest singlet state by ≥10 kcal/mol, are typically short-lived and mostly detected as reactive intermediates. We now report a triplet ground state derivative of aza-m-xylylene diradical with a large singlet-triplet energy gap (ΔE(ST)) of ∼10 kcal/mol, which is comparable to ΔE(ST) for the well-known reactive intermediate m-xylylene diradical. The aminyl diradical persists in solution at room temperature on the time scale of minutes.
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