How Single and Bifurcated Hydrogen Bonds Influence Proton‐Migration Rate Constants, Redox, and Electronic Properties of Phenoxyl Radicals

Abstract

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z52368_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.