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Understanding C-H Bond Oxidations: H⋅ and H - Transfer in the Oxidation of Toluene by Permanganate
Abstract
The oxidation of toluene by permanganate has been studied as a model for the oxidation of C-H bonds by metal reagents, metalloenzymes, and metal oxide surfaces. In water, the reaction proceeds by hydride (H - ) transfer from toluene to a permanganate oxygen, whereas in toluene solution, permanganate abstracts a hydrogen atom (H⋅). The ability of permanganate to abstract a hydrogen atom is rationalized on the basis of the strong O-H bond formed on H⋅ addition to permanganate. This approach allows understanding and prediction of the rates of hydrogen atom transfer from substrates to metal active sites.
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Buxton, G. V., Greenstock, C. L., Helman, W. P., & Ross, A. B. (1988) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.555805 · Cited by 12,332
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Stubbe, J., & van der Donk, W. A. (1998) · Chemical Reviews · doi:10.1021/cr9400875 · Cited by 1,377
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Metadata
- Authors
- Gardner, K. A., & Mayer, J. M.
- Venue
- Science
- Published
- 1995-09-29
- Volume
- 269
- Issue
- 5232
- Pages
- 1849-1851
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W1985581256
- Cited by
- 257
- References
- 1
- FWCI
- 10.97
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Understanding C-H Bond Oxidations: H⋅ and H - Transfer in the Oxidation of Toluene by Permanganate. https://app.cochat.ai/papers/10.1126/science.7569922
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- Gardner, K. A., & Mayer, J. M. (1995). Understanding C-H Bond Oxidations: H⋅ and H - Transfer in the Oxidation of Toluene by Permanganate. Science. https://doi.org/10.1126/science.7569922
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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