The Physicochemical Properties of Complexones,
Tetrapyridylporphin Derivatives

N. M. Berezina^a, M. I. Bazanov^a, A. S. Semeikin^a, and M. B. Berezin^b

^a Ivanovo State University of Chemical Technology, Ivanovo, Russia

^b Institute of the Solution Chemistry, Russian Academy of Sciences, Ivanovo, Russia

e-mail: mbb@isc-ras.ru

Received May 6, 2008

Abstract—We synthesized complexones based on tetrapyridylporphin (I), namely, tetra(pyridinium-4-N-car-
boxymethylene)porphin tetrachloride (II), tetra(pyridinium-4-N-carboxymethylene)porphin tetrabromide
(III), complete ethyl ester of (pyridinium-4-N-carboxymethylene)porphin tetrachloride (IV), and tetra(pyridin-
ium-4-N-methyl)porphin tetraiodide (V). Data on the electronic absorption spectra of the compounds, the
enthalpies of their solution in water, and the enthalpies of complex formation with copper(II) and zinc acetates
were obtained, and the acid properties of the ligands and their stability under thermooxidative destruction con-
ditions were studied. The conclusion was drawn that the enthalpy of solution of complexone-porphyrins in
water was determined by the strength of their crystal lattices and, when different anions (Cl, Br, and I) were
present, by the difference of the enthalpies of their hydration. As distinct from Cu²⁺, complex formation
between Zn²⁺ and porphyrin ligands occurred with sensible energy expenditures likely caused by the electronic
inconsistency between the zinc cation and porphyrin ligands. The stability of water-soluble porphyrins to ther-
mooxidative destruction was limited by temperatures of 200260C.

DOI: 10.1134/S0036024409050185

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