Basicity of Highly Substituted β-Octaalkyl-meso-aryl- and -meso-thienyl Porphyrins

5-Phenyl-, 5,15-diphenyl-5,15-di(thiophen-2-yl)-, and 5,10,15,20-tetraphenyloctaalkyl-21 H ,23 H -porphyrins in benzene–acetic acid mixtures are moderate bases (p K –0.27 to–2.48). There is no simple correlation between the basicity constants and any electronic or geometric structure parameter of th...

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Bibliographic Details
Published in:	Russian journal of organic chemistry Vol. 54; no. 10; pp. 1553 - 1558
Main Authors:	Nikitin, A. A., Klyueva, M. E., Lomova, T. N.
Format:	Journal Article
Language:	English
Published:	Moscow Pleiades Publishing 01-10-2018 Springer Nature B.V
Subjects:	Acetic acid Aromatic compounds Basicity Benzene Chemistry Chemistry and Materials Science Molecular structure Organic Chemistry Planar structures Porphyrins Substitutes
Online Access:	Get full text
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Summary:	5-Phenyl-, 5,15-diphenyl-5,15-di(thiophen-2-yl)-, and 5,10,15,20-tetraphenyloctaalkyl-21 H ,23 H -porphyrins in benzene–acetic acid mixtures are moderate bases (p K –0.27 to–2.48). There is no simple correlation between the basicity constants and any electronic or geometric structure parameter of their molecules due to the contributions of three factors to the basicity: distortion of the planar structure in highly substituted macrocycles and their protonated forms, positive charge delocalization over the conjugated bond system, and electronic effects of substituents.
ISSN:	1070-4280 1608-3393
DOI:	10.1134/S1070428018100184