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


Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

5-Phenyl-, 5,15-diphenyl-5,15-di(thiophen-2-yl)-, and 5,10,15,20-tetraphenyloctaalkyl-21H,23H-porphyrins in benzene–acetic acid mixtures are moderate bases (pK–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.

About the authors

M. E. Klyueva

Ivanovo State Medical Academy

Email: tnl@isc-ras.ru
Russian Federation, Sheremetevskii pr. 8, Ivanovo, 153012

T. N. Lomova

Krestov Institute of Solution Chemistry

Author for correspondence.
Email: tnl@isc-ras.ru
Russian Federation, ul. Akademicheskaya 1, Ivanovo, 153045

A. A. Nikitin

Ivanovo State University of Chemistry and Technology

Email: tnl@isc-ras.ru
Russian Federation, Sheremetevskii pr. 7, Ivanovo, 153000

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2018 Pleiades Publishing, Ltd.