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Issue 14, 2004
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Rate constants for hydrogen abstraction from alkoxides by a perfluoroalkyl radical. An oxyanion accelerated process

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Abstract

A combination of laser flash photolysis and competitive kinetic methods has been used to measure the absolute bimolecular rate constants for hydrogen atom abstraction in water from a series of fluorinated alkoxides and aldehyde hydrates by the perfluoroalkyl radical, ˙CF2CF2OCF2CF2SO3 Na+. The bimolecular rate constants observed for the β-fluorinated alkoxides were in the 105 M−1 s−1 range, such rates representing enhancements (relative to the respective alcohols) of between 100 and almost 1000-fold, depending on the reactivity of the alkoxide. Likewise, the monobasic sodium salts of chloral and fluoral hydrate exhibit similar rate enhancements, relative to their respective hydrates.

Graphical abstract: Rate constants for hydrogen abstraction from alkoxides by a perfluoroalkyl radical. An oxyanion accelerated process

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Publication details

The article was received on 05 Apr 2004, accepted on 26 May 2004 and first published on 24 Jun 2004


Article type: Paper
DOI: 10.1039/B405074F
Org. Biomol. Chem., 2004,2, 2083-2086

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    Rate constants for hydrogen abstraction from alkoxides by a perfluoroalkyl radical. An oxyanion accelerated process

    J. A. Cradlebaugh, L. Zhang, G. R. Shelton, G. Litwinienko, B. E. Smart, K. U. Ingold and W. R. Dolbier, Jr., Org. Biomol. Chem., 2004, 2, 2083
    DOI: 10.1039/B405074F

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