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Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1553–1558 | Cite as

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

  • A. A. Nikitin
  • M. E. Klyueva
  • T. N. Lomova
Article
  • 8 Downloads

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.

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.Ivanovo State University of Chemistry and TechnologyIvanovoRussia
  2. 2.Ivanovo State Medical AcademyIvanovoRussia
  3. 3.Krestov Institute of Solution ChemistryRussian Academy of SciencesIvanovoRussia

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