Synthesis and kinetic investigation of the atropisomerization of meso-tetra(2-cyanophenyl)porphine.
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概要
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Tetra(2-cyanophenyl)porphine (ToCNPP) has been synthesized and isolated into the four respective atropisomers. The rotation of a cyanophenyl ring about the bond to the methine carbon of the porphyrin leads to interconversion reactions among the isomers. The isomerization reactions have been studied kinetically by the separation and quantitative measurement of each isomer on thin layer chromatography plates. The results show that the free energy of activation for the hindered rotation is an average of Δ<I>G</I><SUP>*</SUP>=110 kJ/mol at 50 °C. This is the highest barrier ever measured in similar porphyrin atropisomers. The apparent interaction between adjacent cyano groups is observed. The energy of interaction is estimated to be about 2.0 kJ per mole unit of interaction.
- 公益社団法人 日本化学会の論文
著者
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Anzai Kazunori
Department Of Bioregulation Research National Institute Of Radiological Sciences
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Hatano Keiichiro
Department Of Pharmaceutical Science Nagoya City University
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Anzai Kazunori
Department of Pharmaceutical Sciences, Nagoya City University
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Kubo Tadashi
Department of Pharmaceutical Sciences, Nagoya City University
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Tamai Shoko
Department of Pharmaceutical Sciences, Nagoya City University
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