ArticleJournal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry2019
Experimental and theoretical studies of the porphyrin ligand effect on the electronic structure and reactivity of oxoiron(iv) porphyrin π-cation-radical complexes.
Article in Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 33 citations in OpenAlex.
- Review
- Water-Soluble Iron Porphyrins as Catalysts for Suppressing Chlorinated Disinfection Byproducts in Hypochlorite-Dependent Water Remediation.ChemSusChem · 2025Article
- Theoretical Investigation of Electric Polarizability in Porphyrin-Zinc and Porphyrin-Zinc-Thiazole Complexes Using Small Property-Oriented Basis Sets.International journal of molecular sciences · 2024Article
- A Porphyrin Iron(III) π-Dication Species and its Relevance in Catalyst Design for the Umpolung of Nucleophiles.Angewandte Chemie (International ed. in English) · 2023Article
- Factors controlling the reactivity of synthetic compound-I Analogs.Journal of porphyrins and phthalocyanines · 2023Article
- Toward Environmentally Benign Electrophilic Chlorinations: From Chloroperoxidase to Bioinspired Isoporphyrins.Inorganic chemistry · 2022Article
- Heme compound II models in chemoselectivity and disproportionation reactions.Chemical science · 2022Article
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4 authors at 2 institutions in 1 country.
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Abstract
Oxoiron(IV) porphyrin π-cation-radical complexes (Cpd I) have been studied as models for reactive intermediates called compound I in cytochromes P450, peroxidases, and catalases. It has been well known that the electronic structure and reactivity of Cpd I are modulated by the substituted position and the electron-withdrawing ability of the substituent. However, there still remain two major questions: (1) how many electronegative halogen atoms should be introduced in the meso-phenyl group to switch the porphyrin π-cation-radical state of Cpd I? (2) How does the electron-withdrawing effect of the substituent modulate the reactivity of Cpd I? To answer these two questions, we here performed experimental and theoretical studies on the electron-withdrawing effect of the meso-substituent. We gradually increased the electron-withdrawing effect by increasing the number of fluorine atoms in the meso-phenyl group. Spectroscopic analyses of these Cpd I models reveal that the porphyrin radical state shifts from having a
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