2007/01/27 by Tony Ly, Michael R. Krout, Don K. Pham +3 · 1 citation
Chemistry · Physics and Astronomy · #Chemical Reaction Mechanisms #Molecular Spectroscopy and Structure #Advanced Chemical Physics Studies
paper · doi:10.1021/ja067703m
openalex publication_date 2007/01/27 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/01
The chemical properties of an extremely twisted amide are examined quantitatively for the first time. The predicted high basicity of 2-quinuclidonium is confirmed experimentally by measuring the gas-phase proton affinity using the extended kinetic method. Fragmentation of this molecule further reveals that the lack of resonance stabilization weakens the amide bond. Furthermore, a new route for synthesizing 2-quinuclidonium by eliminating water is demonstrated in the gas phase.