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ISSN 1998-9539

The Effect of Selective Halogenation of Tetrapyrrolic Macrocycle on Binding Ability of Zn-Tetraarylporphyrins towards Small Organic Molecules

Olga A. Dmitrieva,a Mikhail O. Koifman,b Ulyana M. Derbyshina,a Natalya V. Chizhova,a and Nugzar Z. Mamardashvilia@
aG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 153045 Ivanovo, Russian Federation
bIvanovo State University of Chemistry and Technology, 153000 Ivanovo, Russian Federation
@Corresponding author E-mail: ngm@isc-ras.ru
 
DOI: 10.6060/mhc191282m
Macroheterocycles 2020 13(1) 37-43
 

Processes of axial coordination of small organic molecules (imidazole, histidine, methyl ethers of p-aminobenzoic acid and valine) with Zn(II)-tetraarylporphyrins with different numbers of chlorine and bromine atoms in pyrrole and phenyl fragments of the macrocycle were studied by the methods of spectrophotometric titration and 1H NMR spectroscopy. Using quantum chemical calculations, the degree of distortion of the porphyrin macrocycle was determined as halogen atoms were consistently introduced into the macrocycle and the structures of the axial complexes of the studied zinc porphyrinates with ligands of various nature were optimized. The stability constants of the obtained complexes were calculated and a correspondence was found between the experimental, thermodynamic and calculated values of the Zn-L bond energy in the corresponding complexes.

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