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On the Molecular Stereochemistry of the 21,22,23-trimethyl-5,10,15,20-Tetraphenylporphyrin Cation

MATHIAS O. SENGE

Institut für Organische Chemie (WE02), Fachbereich Chemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany

Corresponding author: Institut für Organische Chemie (WE02), Fachbereich Chemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany.

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https://doi.org/10.1002/(SICI)1099-1409(199903)3:3<216::AID-JPP125>3.0.CO;2-BCited by:7 (Source: Crossref)

Abstract

The crystal structure of the triflate salt of the title compound, [Me₃TPP][CF₃SO₃], was investigated to obtain structural information on the conformation of N-trimethylated 5,10,15,20-tetraarylporphyrins. The molecular stereochemistry of the cation is characterized by an up/down/up arrangement for the three N-methyl groups with significant pyramidalization at the nitrogen atoms. The macrocycle is severely distorted with an average deviation from planarity of 0.438 Å. The distortion mode is an asymmetric saddle with deviations from the 4N plane of the C_b atoms at N-methylated pyrrole rings exceeding 1.1 Å. The out-of-plane displacements of pyrrole ring IV are significantly smaller than those of the methylated pyrrole rings.

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