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Synthesis and spectrophotometric study of the acid-base and complexing properties of 2,3,7,8,12,13,17,18-Octaethyl-5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin in acetonitrile

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Abstract

2,3,7,8,12,13,17,18-Octaethyl-5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin has been synthesized, and its acid-base and complexing properties in the systems 1,8-diazabicyclo[5.4.0]undec-7-ene-acetonitrile, acetonitrile-Zn(OAc)2, and 1,8-diazabicyclo[5.4.0]undec-7-ene-acetonitrile-Zn(OAc)2 have been studied by spectrophotometry. Titration of 2,3,7,8,12,13,17,18-octaethyl-5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin with 1,8-diazabicyclo[5.4.0]undec-7-ene is accompanied by successive deprotonation of the pyrrole nitrogen atoms with formation of the corresponding mono- and dianion. The overall acid dissociation constant of the title compound has been determined. The complexation of neutral and doubly deprotonated 2,3,7,8,12,13,17,18-octaethyl-5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin with Zn(OAc)2 has been studied, and kinetic parameters for the formation of the zinc complex according to the molecular and ionic mechanisms have been determined. Extra coordination of 1,8-diazabicyclo[5.4.0]undec-7-ene by the zinc complex of 2,3,7,8,12,13,17,18-octaethyl-5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin.

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Authors and Affiliations

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

    Yu. B. Ivanova & N. Zh. Mamardashvili

  2. Ivanovo State University of Chemistry and Technology, Ivanovo, Russia

    A. V. Glazunov & A. S. Semeikin

Authors
  1. Yu. B. Ivanova
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  2. N. Zh. Mamardashvili
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  3. A. V. Glazunov
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  4. A. S. Semeikin
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Correspondence to Yu. B. Ivanova.

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Original Russian Text © Yu.B. Ivanova, N.Zh. Mamardashvili, A.V. Glazunov, A.S. Semeikin, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 7, pp. 1211–1217.

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Ivanova, Y.B., Mamardashvili, N.Z., Glazunov, A.V. et al. Synthesis and spectrophotometric study of the acid-base and complexing properties of 2,3,7,8,12,13,17,18-Octaethyl-5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin in acetonitrile. Russ J Gen Chem 84, 1404–1410 (2014). https://doi.org/10.1134/S1070363214070287

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  • DOI: https://doi.org/10.1134/S1070363214070287

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