Synthesis of 2-Quinuclidonium by Eliminating Water: Experimental Quantification of the High Basicity of Extremely Twisted Amides
详细信息 查看全文
- 作者：Tony Ly ; Michael Krout ; Don K. Pham ; Kousuke Tani ; Brian M. Stoltz ; Ryan R. Julian
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：February 21, 2007
- 年：2007
- 卷：129
- 期：7
- 页码：1864 - 1865
- 全文大小：53K
- 年卷期：v.129,no.7(February 21, 2007)
- ISSN：1520-5126
文摘
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.