Published February 21, 2007
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Journal Article
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Synthesis of 2-Quinuclidonium by Eliminating Water: Experimental Quantification of the High Basicity of Extremely Twisted Amides
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.
Additional Information
© 2007 American Chemical Society. Received 27 October 2006. Published online 27 January 2007. Published in print 1 February 2007. We acknowledge funding from the University of California, Riverside, Ono Pharmaceutical Co. Ltd (for a postdoctoral fellowship to K.T.), and Bristol-Myers Squibb. D.K.P. thanks the Kenan Trust and the NSF REU Site in Bioanalytical Science supported by Grant CHE-0552493.Attached Files
Supplemental Material - ja067703msi20070118_030344.pdf
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Additional details
- Eprint ID
- 74456
- Resolver ID
- CaltechAUTHORS:20170222-084852047
- University of California, Riverside
- Ono Pharmaceutical Co. Ltd.
- Bristol-Myers Squibb
- Kenan Trust
- NSF
- CHE-0552493
- Created
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2017-02-22Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field