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

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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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Authors and Affiliations

  1. Ivanovo State University of Chemistry and Technology, Sheremetevskii pr. 7, Ivanovo, 153000, Russia

    A. A. Nikitin

  2. Ivanovo State Medical Academy, Sheremetevskii pr. 8, Ivanovo, 153012, Russia

    M. E. Klyueva

  3. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, ul. Akademicheskaya 1, Ivanovo, 153045, Russia

    T. N. Lomova

Authors
  1. A. A. Nikitin
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  2. M. E. Klyueva
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  3. T. N. Lomova
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Correspondence to T. N. Lomova.

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Original Russian Text © A.A. Nikitin, M.E. Klyueva, T.N. Lomova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 10, pp. 1540–1545.

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Nikitin, A.A., Klyueva, M.E. & Lomova, T.N. Basicity of Highly Substituted β-Octaalkyl-meso-aryl- and -meso-thienyl Porphyrins. Russ J Org Chem 54, 1553–1558 (2018). https://doi.org/10.1134/S1070428018100184

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  • DOI: https://doi.org/10.1134/S1070428018100184

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