105705-25-7Relevant academic research and scientific papers
Methylviologen-pendant iron porphyrins as models of a reduction enzyme: Six-electron reduction of nitrobenzene to aniline
Koga, Hiroaki,Hamada, Taisuke,Sakaki, Shigeyoshi
, p. 1153 - 1160 (2007/10/03)
Methylviologen-pendant iron porphyrins, in which methylviologen was introduced to the weso-phenyl group through an amido-bridge at either the p- or m-position, were newly synthesized, in expectation that these methylviologen-pendant iron porphyrins would be good functional models of a multi-electron reductase such as nitrite reductase since the methylviologen-pendant can play the role of an electron-trapping and storage unit like the iron-sulfur cluster of the nitrite reductase. These iron porphyrins were successfully applied to the six-electron reduction of nitrobenzene to aniline, which is a model reaction of nitrite reduction to ammonia catalyzed by nitrite reductase. Both p- and m-methylviologen-pendant iron porphyrins give somewhat larger yields of aniline in the reduction of nitrobenzene and much larger yields of p-methoxyaniline in the reduction of p-nitroanisole than does normal iron tetraphenylporphyrin. Though normal iron tetraphenylporphyrin can not catalyze well the reduction of p-nitroanisole in the presence of the dioxygen molecule, these methylviologen-pendant iron porphyrins can catalyze well the reduction of p-nitroanisole and give a considerably larger yield of p-methoxyaniline even in the presence of the dioxygen molecule. These methylviologen-pendant iron porphyrins give a much larger yield of aniline in the reduction of nitrosobenzene and somewhat larger yield of aniline in the reduction of phenylhydroxylamine than does iron tetraphenylporphyrin. m-Methylviologen-pendant iron porphyrin exhibits higher catalytic activity than does the p-pendant one. The role of methylviologen moiety is discussed, based on cyclic voltammograms and UV-VIS spectra of these iron porphyrins. The Royal Society of Chemistry 2003.
The Synthesis and Proton Nuclear Magnetic Resonance Study of some Nitro- and Amino-unsymmetrically meta-Substituted Tetraphenylporphyrins
Sun, Yizhen,Martell, Arthur E.,Tsutsui, Minoru
, p. 561 - 565 (2007/10/02)
Procedures for the synthesis of new partially-substituted mesotetraphenylporphyrins (TPP's) are described.The 5-(3-nitrophenyl)-10,15,20-triphenylporphyrin is the primary product from a 1:2:3 molar ratio of m-nitrobenzaldehyde, benzaldehyde and pyrrole.The crude reaction product also contained TPP, 5,10-bis(3-nitrophenyl)-15,20-diphenylporphyrin. 5,15-bis(3-nitrophenyl)-10,20-diphenylporphyrin, and 5,10,15-tris(3-nitrophenyl)-20-phenylporphyrin.The crude mixture of m-nitrophenylporphyrins was reduced to a mixture of the corresponding amino derivatives, which was separated into TPP, 5-(3-aminophenyl)-10,15,20-triphenylporphyrin, 5,10-bis(3-aminophenyl)-15,20-diphenylporphyrin, and 5,15-bis(3-aminophenyl)-10,20-diphenylporphyrin.The products were characterized by uv-visible and ir spectrophotometry, and by high resolution nmr spectroscopy and mass spectroscopy.
