Acid–Base Properties of Polyhalogenated Tetraphenylporphyrins

[2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) and [2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) were synthesized by halogenation of [5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) with N -bromo...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-06, Vol.56 (6), p.1054-1061
Main Authors: Ivanova, Yu. B., Chizhova, N. V., Shumilova, I. A., Rusanov, A. I., Mamardashvili, N. Zh
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:[2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) and [2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) were synthesized by halogenation of [5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) with N -bromosuccinimide and N -chlorosuccinimide, respectively, in a mixture of chloroform with methanol. Treatment of the halogenated zinc porphyrins with trifluoroacetic acid in chloroform gave the corresponding free ligands. The isolated compounds were identified by electronic absorption, 1 H NMR, and mass spectra. The acid–base properties of 5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin, 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin, and 2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin were studied in acetonitrile at 298 K. Their acidity and basicity constants and concentration ranges of their ionized forms were determined.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020060147