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Synthesis, characterization, and reactivity of hypochloritoiron(III) porphyrin complexes. 2012

Zhiqi Cong, and Sachiko Yanagisawa, and Takuya Kurahashi, and Takashi Ogura, and Satoru Nakashima, and Hiroshi Fujii
Institute for Molecular Science and Okazaki Institute for Integrative Bioscience, National Institutes of Natural Sciences, Myodaiji, Okazaki 444-8787, Japan.

A hypochloritoiron(III) porphyrin species has been proposed as a key intermediate in an antimicrobial defense system in neutrophils and in heme-catalyzed chlorination reactions. We report herein the preparation, spectroscopic characterization, and reactivity of the bis(hypochlorito)iron(III) porphyrin complex [(TPFP)Fe(III)(OCl)(2)](-) (1) and the imidazole-hypochloritoiron complexes (TPFP)Fe(III)(OCl)(1-R-Im) [R = CH(3) (2), H (3), CH(2)CO(2)H (4)], in which TPFP is 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinate. The structures of 1-4 were confirmed by absorption, (2)H and (19)F NMR, EPR, and resonance Raman spectroscopy and electrospray ionization mass spectrometry at low temperature. The reactions of 1 and 2 with various organic substrates show that 1 and 2 are capable of chlorination, sulfoxidation, and epoxidation reactions and that 1 is much more reactive with these substrates than 2.

UI MeSH Term Description Entries
D006997 Hypochlorous Acid An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent. Hypochlorite,Hypochlorous Acids
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D011166 Porphyrins A group of compounds containing the porphin structure, four pyrrole rings connected by methine bridges in a cyclic configuration to which a variety of side chains are attached. The nature of the side chain is indicated by a prefix, as uroporphyrin, hematoporphyrin, etc. The porphyrins, in combination with iron, form the heme component in biologically significant compounds such as hemoglobin and myoglobin. Porphyrin
D004852 Epoxy Compounds Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS. Epoxide,Epoxides,Epoxy Compound,Oxiranes,Compound, Epoxy,Compounds, Epoxy
D005290 Ferric Compounds Inorganic or organic compounds containing trivalent iron. Compounds, Ferric
D006843 Hydrocarbons, Chlorinated Hydrocarbon compounds with one or more of the hydrogens replaced by CHLORINE. Chlorinated Hydrocarbon,Chlorinated Hydrocarbons,Organochlorine Compound,Chlorine Compounds, Organic,Organochlorine Compounds,Compound, Organochlorine,Compounds, Organic Chlorine,Compounds, Organochlorine,Hydrocarbon, Chlorinated,Organic Chlorine Compounds
D013057 Spectrum Analysis The measurement of the amplitude of the components of a complex waveform throughout the frequency range of the waveform. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Spectroscopy,Analysis, Spectrum,Spectrometry
D013454 Sulfoxides Organic compounds that have the general formula R-SO-R. They are obtained by oxidation of mercaptans (analogous to the ketones). (From Hackh's Chemical Dictionary, 4th ed)
D054879 Halogenation Covalent attachment of HALOGENS to other compounds. Bromination,Chlorination,Fluorination,Iodination,Iodation

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