Synthesis of 2-quinuclidonium by eliminating water: experimental quantification of the high basicity of extremely twisted amides

Tony Ly, Michael Krout, Don K. Pham, Kousuke Tani, Brian M. Stoltz, Ryan R. Julian

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)1864-1865
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number7
DOIs
Publication statusPublished - 21 Feb 2007

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