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Spin Trapping Chemistry of Iminyl Free Radicals

✍ Scribed by Edward G. Janzen; Dale E. Nutter

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
408 KB
Volume
35
Category
Article
ISSN
0749-1581

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✦ Synopsis

The iminyl radicals formed from hydrogen atom abstraction between tert-butoxyl radicals and benzylidene-Nalkyl-or N-arylamines were trapped by 2-methyl-2-nitrosopropane and investigated by EPR spectroscopy. The compounds investigated were benzylidene N-methyl, ethyl, 1-propyl, 1-butyl, 2-methylpropyl, 1-methylethyl, 1methylpropyl, 1-ethylpropyl, 1-methylbutyl and cyclohexyl derivative and also benzylidene N-phenyl, 4-tolyl, 4-Ñuorophenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl and 4-triÑuoromethylphenyl derivatives. In every case the iminyl nitroxide (aminoxyl) was produced in benzene at room temperature. The nitrogen hyperÐne splitting constants were in the ranges 3.39-3.56 and 9.68-9.77 G for the iminyl and nitroxyl nitrogens, respectively, for the benzylidene-N-alkylamines and 3.60-3.77 and 8.45-9.15 G for the iminyl and nitroxyl nitrogens, respectively, for the benzylidene-N-arylamines. Very little evidence was found for hydrogen atom abstraction from the alkyl groups attached to the imine function. The absolute rate constant for hydrogen atom abstraction of the iminyl hydrogen was estimated to be 1.2 Â 104 M-1 s-1 based on competitive experiments with addition of tert-butoxyl radicals to 2-methyl-2-nitrosopropane (1.5 Â 106 M-1 s-1). This value is considerably slower than that for benzaldehyde (2.4 Â 107 M-1 s-1).

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