Studies in Oxidative Chemistry: Oxidation of Benz[a]anthracene Using a Synthetic Porphyrin Catalyst to Model Cytochrome P-450
Public Deposited- Last Modified
- February 28, 2019
- Creator
-
Brust, Kirstin
- Affiliation: Gillings School of Global Public Health, Department of Environmental Sciences and Engineering
- Abstract
- Oxidations of the PAH benz[a]alanthracene were carried out using m-chloroperoxybenzoic acid as monooxygen donor and the 2,6-chlorotetraphenyl-substituted iron porphyrin as catalyst. These reactions were performed in two different modes. The first used the oxoferryl porphyrin cation radical as direct oxidant, essentially allowing only one turnover of catalyst, whereas the second used the high-valent complex in a multi-turnover, catalytic mode. Phenoxathiin hexachloroantimonate was used as a model one-electron oxidant to compare its product profile to the other modes. Identical products (or substitution at the same carbon) in the other modes would provide support for a one-electron pathway. 18^0-labelled mCPBA was used in oxidations to provide direct evidence for involvement of the peroxyacid as the monooxygen donor, and 18^0 incorporation in the oxidized PAH was observed. Analysis of the product profiles in the three different oxidations supports one-electron oxidation as the major pathway operating. The products of the porphinatoiron-mediated oxidation are also postulated to depend on the relative amounts of substrate and available catalyst present during the oxidation.
- Date of publication
- January 1991
- DOI
- Resource type
- Rights statement
- In Copyright
- Advisor
- Aitken, Michael
- Ball, Louise
- Gold, Avram
- Degree
- Master of Science in Public Health
- Academic concentration
- Environmental Chemistry and Biology
- Degree granting institution
- University of North Carolina at Chapel Hill
- Graduation year
- 1991
- Language
- Deposit record
- c2589085-57f7-4434-bf45-a2666ba162b9
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