Atropisomerism of zinc tetrakis(o-cyanophenyl)porphyrins. The crystal structure of the .ALPHA..BETA..ALPHA..BETA.-isomer and the atropisomerization rates.

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概要

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• The structure of one of the four atropisomers of tetrakis(<I>o</I>-cyanophenyl)porphyrin has been determined as the zinc complex by X-ray crystallographic methods. The five-coordinate zinc porphyrin with pyridine as the axial ligand also has a pyridine solvate in the crystal lattice. The conformation of the <I>o</I>-cyanophenyl rings is αβαβ as predicted previously. The two nitrogen atoms of the CN groups on the same side of the coordinated pyridine have close <I>intramolecular</I> contacts to pyridine at the van der Waals distance. However, the structural parameters, bond distances and angles of this molecule do not indicate distinct steric effects of the CN groups. Thermal atropisomerization among the four zinc porphyrin atropisomers occurs in solution. The quantitative composition of the atropisomers at equilibrium and the rates of the isomerization reaction have been determined with aliquots separated by TLC. A nonstatistical equilibrium distribution of the atropisomers suggests some mutual interactions among the CN groups. The slower isomerization rates of the zinc complexes compared to those of the free base have been discussed in connection with the molecular structure.

• 公益社団法人 日本化学会の論文

著者

• Iitaka Yoichi

  Faculty Of Medicine Teikyo University

• Hatano Keiichiro

  Department Of Pharmaceutical Science Nagoya City University

• Kawasaki Kyoko

  Department of Pharmaceutical Sciences, Nagoya City University

• Munakata Sonono

  Department of Pharmaceutical Sciences, Nagoya City University

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