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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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Litwinienko, Grzegorz, Ingold, K. U.·2003·The Journal of Organic Chemistry
DOI 10.1021/jo026917t
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Abstract

Rate constants, k(ArOH/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 k(ArOH/dpph*)(S) values of 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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Metadata

Authors
Litwinienko, G., & Ingold, K. U.
Venue
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Published
2003-04-02
Volume
68
Issue
9
Pages
3433-3438
ISSN
  • 0022-3263 (ISSN-L)
  • 1520-6904
DOI
10.1021/jo026917t
OpenAlex
W2077139480
Cited by
412
References
0
FWCI
11.51
Type
journal article
Language
en
Open access
green

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CoChat. (2026). Citation check: Abnormal Solvent Effects on Hydrogen Atom Abstractions. 1. The Reactions of Phenols with 2,2-Diphenyl-1-picrylhydrazyl (dpph•) in Alcohols. https://app.cochat.ai/papers/10.1021/jo026917t
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Litwinienko, G., & Ingold, K. U. (2003). Abnormal Solvent Effects on Hydrogen Atom Abstractions. 1. The Reactions of Phenols with 2,2-Diphenyl-1-picrylhydrazyl (dpph•) in Alcohols. The Journal of Organic Chemistry. https://doi.org/10.1021/jo026917t

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Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.