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Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph•) in alcohols

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DOIResolve DOI: https://doi.org/10.1021/jo026917t
AuthorSearch for: 1; Search for: 1
Affiliation
  1. National Research Council of Canada
FormatText, Article
Subjectalcohols; hydrogen bonds; ionization; phenols; rate constants; atom abstractions; organic solvents; 1,1 diphenyl 2 picrylhydrazyl; alcohol; heptane; hydrogen; phenol derivative; solvent; antioxidant activity; chemical structure; electron transport; hydrogen bond; ionization
Abstract
Rate constants, kArOH/dpph•,s, for hydrogen atom abstraction from 13 hindered and nonhindered phenols by the diphenylpicrylhydrazyl radical, dpph•, have been determined in n-heptane and a number of alcoholic and nonalcoholic, hydrogen-bond accepting solvents. Abnormally enhanced values of kArOH/dpph•,s have been observed in alcohols. It is proposed that this is due to partial ionization of the phenols and a very fast electron transfer from phenoxide anion to dpph•. The popular assessment of the antioxidant activities of phenols with dpph• in alcohol solvents will generally lead to an overestimation of their activities.
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  • Journal of Organic Chemistry 68, no. 9 (2 April 2003): 3433–3438.
LanguageEnglish
Peer reviewedYes
NPARC number21276585
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Record identifier2521451d-b01a-47b2-ab03-ba7f41d70eb5
Record created2015-10-13
Record modified2020-06-02
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