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Oxidative N-dealkylation reactions by oxoiron(IV) complexes of nonheme and heme ligands
- Oxidative N-dealkylation reactions by oxoiron(IV) complexes of nonheme and heme ligands
- Nehru K.; Seo M.S.; Kim J.; Nam W.
- Ewha Authors
- 남원우; 김진흥; 서미숙
- SCOPUS Author ID
- 남원우; 김진흥
- Issue Date
- Journal Title
- Inorganic Chemistry
- vol. 46, no. 1, pp. 293 - 298
- SCI; SCIE; SCOPUS
- Nonheme and heme iron monooxygenases participate in oxidative N-dealkylation reactions in nature, and high-valent oxoiron(IV) species have been invoked as active oxidants that effect the oxygenation of organic substrates. The present study describes the first example of the oxidative N-dealkylation of N,N-dialkylamines by synthetic nonheme oxoiron(IV) complexes and the reactivity comparisons of nonheme and heme oxoiron(IV) complexes. Detailed mechanistic studies were performed with various N,N-dialkylaniline substrates such as para-substituted N,N-dimethylanilines, para-chloro-N-ethyl-N- methylaniline, para-chloro-N-cyclopropyl-N-isopropylaniline, and deuteriated N,N-dimethylanilines. The results of a linear free-energy correlation, inter- and intramolecular kinetic isotope effects, and product analysis studied with the mechanistic probes demonstrate that the oxidative N-dealkylation reactions by nonheme and heme oxoiron(IV) complexes occur via an electron transfer-proton transfer (ET-PT) mechanism. © 2007 American Chemical Society.
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