Reaction of phenols with the 2, 2-diphenyl-1-picrylhydrazyl radical. Kinetics and DFT calculations applied to determine ArO-H bond dissociation enthalpies and …

…, C Daquino, ID Mackie, GA DiLabio…

Index: Foti, Mario C.; Daquino, Carmelo; Mackie, Iain D.; DiLabio, Gino A.; Ingold Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9270 - 9282

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Citation Number: 96

Abstract

The formal H-atom abstraction by the 2, 2-diphenyl-1-picrylhydrazyl (dpph•) radical from 27 phenols and two unsaturated hydrocarbons has been investigated by a combination of kinetic measurements in apolar solvents and density functional theory (DFT). The computed minimum energy structure of dpph• shows that the access to its divalent N is strongly hindered by an ortho H atom on each of the phenyl rings and by the o-NO2 groups of the ...