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

doi:10.1021/ja067703m

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 journal › Article › peer-review

32 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 language	English
Pages (from-to)	1864-1865
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	7
DOIs	https://doi.org/10.1021/ja067703m
Publication status	Published - 21 Feb 2007

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title = "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.",

author = "Tony Ly and Michael Krout and Pham, \{Don K.\} and Kousuke Tani and Stoltz, \{Brian M.\} and Julian, \{Ryan R.\}",

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AU - Ly, Tony

AU - Krout, Michael

AU - Pham, Don K.

AU - Tani, Kousuke

AU - Stoltz, Brian M.

AU - Julian, Ryan R.

PY - 2007/2/21

Y1 - 2007/2/21

N2 - 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.

AB - 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.

U2 - 10.1021/ja067703m

DO - 10.1021/ja067703m

M3 - Article

SN - 0002-7863

VL - 129

SP - 1864

EP - 1865

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 7

ER -

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

Abstract

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