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Hydrogen Atom Abstraction Kinetics from Intramolecularly Hydrogen Bonded Ubiquinol-0 and Other (Poly)methoxy Phenols
Abstract
The effect of methoxy substitution on the abstraction of the phenolic hydrogen atom involved in intramolecular hydrogen bonding by tert -butoxyl and cumyloxyl radicals has been investigated by laser flash photolysis. Also transition state calculations for methoxyl radical and 2-methoxyphenol have been carried out by a density functional theory (DFT) method. Hydrogen atom abstraction is surprisingly easy from intramolecularly hydrogen bonded methoxyphenols, in contrast to intermolecularly hydrogen bonded molecules. The kinetic solvent effect, investigated in six solvents with different hydrogen bond accepting properties, on the hydrogen atom abstraction reaction from o -methoxy phenols was shown to be smaller than for non-hydrogen bonded phenols, and is independent of further methoxy substitution. The high rate constant for hydrogen atom abstraction from ubiquinol-0 (2.8 × 10 9 M - 1 s - 1 in CCl 4 ) and the small kinetic solvent effect make it a good antioxidant, even in a polar environment.
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Cited by
Foti, M. C., Daquino, C., & Geraci, C. (2004) · The Journal of Organic Chemistry · doi:10.1021/jo035758q · Cited by 599
Ingold, K. U., & Pratt, D. A. (2014) · Chemical Reviews · doi:10.1021/cr500226n · Cited by 531
Self-citationBarclay, L. R. C., Vinqvist, M. R., Mukai, K., Goto, H., Hashimoto, Y., Tokunaga, A., & Uno, H. (2000) · Organic Letters · doi:10.1021/ol000173t · Cited by 301
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
Cheng, J.-C., Dai, F., Zhou, B., Yang, L., & Liu, Z.-L. (2007) · Food Chemistry · doi:10.1016/j.foodchem.2006.11.012 · Cited by 205
Metadata
- Authors
- de Heer, M. I., Mulder, P., Korth, H.-G., Ingold, K. U., & Lusztyk, J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-02-26
- Volume
- 122
- Issue
- 10
- Pages
- 2355-2360
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2081274731
- Cited by
- 184
- References
- 0
- FWCI
- 9.59
- Type
- journal article
- Language
- en
- Open access
- closed
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- de Heer, M. I., Mulder, P., Korth, H.-G., Ingold, K. U., & Lusztyk, J. (2000). Hydrogen Atom Abstraction Kinetics from Intramolecularly Hydrogen Bonded Ubiquinol-0 and Other (Poly)methoxy Phenols. Journal of the American Chemical Society. https://doi.org/10.1021/ja9937674
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