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Title: Comparative analysis of tetrapyrrolic macrocyle structure of tri-, tetra-, and undecasubstituted free base corroles
Authors: Klenitsky, D.V.
Kruk, M.M.
MAES, Wouter 
Issue Date: 2017
Source: Proceedings of BSTU, 2(1), p. 23-28
Abstract: The comparative analysis of the structure of tetrapyrrolic macrocycle of free base corroles, which differ in the peripheral substitution type, has been carried out. It has been found that tri- and tetrasubstituted corrole derivatives reveal the wave-type nonplanar distortions, whereas undecasubstituted (in the meso-positions and all the pyrrole rings) derivative has saddle-type distorted macrocycle. The degree of nonplanar distortions of corroles macrocycle has been determined with the Δ23 parameter, which is the average least-square deviation from the mean macrocycle plane C7 per one macrocycle atom. While the tri- and tetrasubstituted corrole derivatives with aryl substituents in the meso-positions reveal similar Δ23 values ranging from 0.200 to 0.215 Å, the undecasubstitution induces substantial increase in the amplitude of atoms deviation from the mean plane (Δ23 = 0.503 Å). Strong steric interaction between peripheral substituents leads to the pyrrole rings А, B and C are substantially tilted relative to the mean macrocycle plane 7C. These differences indicate that tetrapyrrolic macrocycle of the free base corroles has wave-like conformation in the absence of steric interactions with peripheral substituents, which holds upon weak steric interactions. When the eight bulky substituents introduced the conformational transition from the wave- to saddle-type distorted conformer takes place as a result of the enhancement of steric interactions.
Keywords: corrole; macrocycle mean plane; nonplanar distortions; conformers
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ISSN: 1683-0377
Category: A2
Type: Journal Contribution
Appears in Collections:Research publications

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