Issue 14, 2004

Large primary kinetic isotope effects in the abstraction of hydrogen from organic compounds by a fluorinated radical in water

Abstract

Isotope effects have been measured for the abstraction of hydrogen from a series of organic substrates by the perfluoro radical, Na+O3SCF2CF2OCF2CF2˙, in water. Both primary and secondary deuterium isotope effects were measured, with the primary isotope effects ranging in value from 4.5 for isopropanol to 19.6 for acetic acid. The values for the α- and β-secondary deuterium isotope effects were 1.06 and 1.035, respectively. It was concluded that tunneling contributes significantly to the production of the observed, large primary kinetic isotope effects in these C–H abstraction reactions.

Graphical abstract: Large primary kinetic isotope effects in the abstraction of hydrogen from organic compounds by a fluorinated radical in water

Article information

Article type
Paper
Submitted
05 Apr 2004
Accepted
26 May 2004
First published
24 Jun 2004

Org. Biomol. Chem., 2004,2, 2087-2091

Large primary kinetic isotope effects in the abstraction of hydrogen from organic compounds by a fluorinated radical in water

J. A. Cradlebaugh, L. Zhang, A. B. Shtarev, B. E. Smart and W. R. Dolbier, Jr., Org. Biomol. Chem., 2004, 2, 2087 DOI: 10.1039/B405075D

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