Hydrogen-bonded phenoxyl radicals are made and the strength of the hydrogen bond between the O(phenoxyl) and the H(ammonium) atoms strongly affects their stability. The rate constants for the intramolecular proton-migration process in these systems are reported and a bifurcated hydrogen-bonded system has been characterized (see model). Investigations show that the proton transfer from the phenoxyl-radical cation to the tertiary amine is assisted by a neighboring nitrogen atom.
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Thomas et al. (2004) studied this question.
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