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Investigation of Acidic and Coordination Properties of Octabromo-Substituted Porphyrins in the System of 1,8-Diazabicyclo[5,4,0]unde-7-ene-Acetonitrile

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Abstract

Acidity and metal ion coordination are described for three porphyrin derivatives, different in their macrocycle conformation and electronic substitution effects due to bromine substitution in pyrrole rings and trifluorometyl or phenyl groups in meso-positions. Combination of these facts allows modulating both steric and electronic effects on the macrocycle π-conjugated system. The role of electronic substitution effects in the macrocycle deprotonation and metal ion complex formation is found dominating with comparable resonance and inductive contributions, whereas non-planar conformation of reactive species contributes to the reaction rates to a lesser extent. The interaction of two single-electron (a1ueg) and (a2ueg) configurations is studied as a function of non-planar distortions of the molecular structure for the three tetrapyrrole compounds. The additive influence of disturbing factors on the configuration interaction of single-electron (a1ueg) and (a2ueg) configurations in the tetrapyrrole macrocycle is demonstrated.

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Authors and Affiliations

  1. Ivanovo State University of Chemistry and Technology, pr. Sheremetevskii 7, Ivanovo, 153460, Russia

    S. G. Pukhovskaya, A. S. Semeikin & S. A. Syrbu

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

    Yu. B. Ivanova

  3. Belarusian State Technological University, ul. Sverdlova 13a, Minsk, 220006, Belarus

    N. N. Kruk

Authors
  1. S. G. Pukhovskaya
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  2. Yu. B. Ivanova
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  3. A. S. Semeikin
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  4. S. A. Syrbu
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  5. N. N. Kruk
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Corresponding authors

Correspondence to S. G. Pukhovskaya, Yu. B. Ivanova or N. N. Kruk.

Additional information

Russian Text © The Author(s), 2017, published in Rossiiskii Khimicheskii Zhurnal, 2017, Vol. 61, No. 1, pp. 56–66.

Funding

This work is performed with financial support of the Russian Foundation for Basic Research (grant no. 16-53-00100 Bel-a).

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No conflict of interest was declared by the authors.

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Pukhovskaya, S.G., Ivanova, Y.B., Semeikin, A.S. et al. Investigation of Acidic and Coordination Properties of Octabromo-Substituted Porphyrins in the System of 1,8-Diazabicyclo[5,4,0]unde-7-ene-Acetonitrile. Russ J Gen Chem 89, 1286–1296 (2019). https://doi.org/10.1134/S1070363219060252

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