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Lim, Mi Hee
MetalloNeuroChemistry Lab (MNCL)
Research Interests
  • Neurodegenerative disease, small molecule design, network between metal, proteins, and ROS

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Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of alkanes

Cited 86 times inthomson ciCited 92 times inthomson ci
Title
Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of alkanes
Author
Nam, WLim, Mi HeeMoon, SKKim, C
Keywords
WATER-SOLUBLE METALLOPORPHYRINS; O BOND-CLEAVAGE; IRON PORPHYRIN; COMPOUND-I; REBOUND MECHANISM; CYTOCHROME-P450; REACTIVITY; EPOXIDATION; ENZYMES; LIGAND
Issue Date
2000-11
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.122, no.44, pp.10805 - 10809
Abstract
We have obtained evidence that acylperoxo-iron(III) porphyrin complexes 1a are involved as reactive hydroxylating intermediates in the hydroxylation of alkanes by m-chloroperoxybenzoic acid (m-CPBA) catalyzed by electron-deficient iron(III) porphyrin complexes containing chloride as an anionic axial ligand in a solvent mixture of CH2Cl2 and CH3CN at -40 °C. In addition to the intermediacy of 1a, oxoiron(IV) porphyrin cation radical complexes 2 are formed as the reactive hydroxylating intermediates in the alkane hydroxylations by m-CPBA catalyzed by the iron(III) porphyrin complexes containing triflate (CF3SO3 -) as an anionic axial ligand under the same reaction conditions. In line with the recent proposal by Newcomb, Coon, Vaz, and co-workers for cytochrome P-450 reactions, these results suggest that two distinct electrophilic oxidants such as 1a and 2 effect the alkane hydroxylations in iron porphyrin models, depending on the reaction conditions such as the nature of the anionic axial ligands of iron(III) porphyrin complexes.
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DOI
10.1021/ja0010554
ISSN
0002-7863
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PHY_Journal Papers
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