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Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals
Abstract
The rates of formal abstraction of phenolic hydrogen atoms by free radicals, Y* + ArOH --> YH + ArO*, are profoundly influenced by the hydrogen-bond-accepting and anion-solvation abilities of solvents, by the electron affinities and reactivities (Y-H bond dissociation enthalpies) of radicals, and by the phenol's ring substituents. These apparently simple reactions can occur by at least three different, nonexclusive mechanisms: hydrogen atom transfer, proton-coupled electron transfer, and sequential proton-loss electron transfer. The delicate balance among these mechanisms depends on both the environment and the reactants. The main features of these mechanisms are described, together with some interesting kinetic consequences.
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Cited by
Thiyl Radicals in Organic Synthesis
Dénès, F., Pichowicz, M., Povie, G., & Renaud, P. (2014) · Chemical Reviews · doi:10.1021/cr400441m · Cited by 985
Understanding Hydrogen Atom Transfer: From Bond Strengths to Marcus Theory
Mayer, J. M. (2011) · Accounts of Chemical Research · doi:10.1021/ar100093z · Cited by 910
ABTS/PP Decolorization Assay of Antioxidant Capacity Reaction Pathways
Ilyasov, I. R., Beloborodov, V. L., Selivanova, I. A., & Terekhov, R. P. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms21031131 · Cited by 543
Ingold, K. U., & Pratt, D. A. (2014) · Chemical Reviews · doi:10.1021/cr500226n · Cited by 531
Self-citationXie, J., & Schaich, K. M. (2014) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf500180u · Cited by 494
Antioxidant properties of phenols
Foti, M. C. (2007) · Journal of Pharmacy and Pharmacology · doi:10.1211/jpp.59.12.0010 · Cited by 382
Pratt, D. A., Tallman, K. A., & Porter, N. A. (2011) · Accounts of Chemical Research · doi:10.1021/ar200024c · Cited by 352
Mastelić, J., Jerković, I., Blažević, I., Poljak-Blaži, M., Borović, S., Ivančić-Baće, I., Smrečki, V., Žarković, N., Brčić-Kostic, K., Vikić-Topić, D., et al. (2008) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf073272v · Cited by 314
Free Radical Scavenging by Natural Polyphenols: Atom versus Electron Transfer
Di Meo, F., Lemaur, V., Cornil, J., Lazzaroni, R., Duroux, J.-L., Olivier, Y., & Trouillas, P. (2013) · The Journal of Physical Chemistry A · doi:10.1021/jp3116319 · Cited by 294
Modified DPPH and ABTS Assays to Assess the Antioxidant Profile of Untreated Oils
Christodouleas, D. C., Fotakis, C., Nikokavoura, A., Papadopoulos, K., & Calokerinos, A. C. (2015) · Food Analytical Methods · doi:10.1007/s12161-014-0005-6 · Cited by 95
Proton-Coupled Redox Switching in an Annulated π-Extended Core-Modified Octaphyrin
Sarma, T., Kim, G., Sen, S., Cha, W.-Y., Duan, Z., Moore, M. D., Lynch, V. M., Zhang, Z., Kim, D., & Sessler, J. L. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b06938 · Cited by 53
Metadata
- Authors
- Litwinienko, G., & Ingold, K. U.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-01-17
- Volume
- 40
- Issue
- 3
- Pages
- 222-230
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- OpenAlex
- W2165062754
- Cited by
- 647
- References
- 0
- FWCI
- 17.88
- Type
- journal article
- Language
- en
- Open access
- closed
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