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The rotation of the amino-phenyl group leads to four atropisomers, stable in solution at room temperature. They have been named ααα α for the isomer with the four amino groups on the same side of the porphyrin, αααβ for the isomer with three amino groups on one side and the fourth one on the other side, ααββ when the porphyrin bears two contiguous amino groups on one face with the two others on the other face. Finally, the amino groups of the isomer αβα β are alternatively on one side and on the other one. They are cited here by decreasing polarity with their statistical abundance in brackets: αααα (12.5%), αααβ(50%), ααββ(25%), αβαβ (12.5%). The abundance of the atropisomer αααα is raised to 70% according to J. Lindsey, J. Org. Chem. 1980, 45, 5215.
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33644753027
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note
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The four meso positions of a porphyrin, composed of the methylene atoms bridging the four pyrrolic units are numbered 5, 10, 15, 20 in the international nomenclature. If two adjacent meso positions are linked, a 5-10 (and 15-20) strap(s) is (are) obtained, while a 5-15 strap results from the linkage of two diametrically opposed meso positions.
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33644779983
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note
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In porphyrin 9, the two ethoxy groups are not magnetically equivalent, as the two pickets are different.
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33644776733
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[33]
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[33]).
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4243564281
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Coutsolelos, A.G.7
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31
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33644754723
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CCDC-278947 to -278949 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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For an interactive introduction to porphyrin distortions and more details about the deviations of each atom, see http://www-chem.ucdavis.edu/groups/ smith/chime/chime_index.html.
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