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Updated: Jun 24, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Beyond 7-azaindole: conjugation effects on intermolecular double hydrogen-atom transfer reactions
Carlos R Baiz1, Sarah J Ledford, Kevin J Kubarych
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Abstract:
Conjugation effects on the thermodynamics of ground-state and lowest-singlet excited-state double hydrogen-atom transfer reactions in 7-azaindole and related models are studied with ab initio electronic structure methods. The results indicate that the extended conjugation of the system has a large effect on the relative energies required for hydrogen-atom transfer. The observed energy differences are mainly attributed to stabilization of the tautomer species by enhancing low-energy resonance structures and by allowing for efficient delocalization of excess charge in the reaction center.
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