Abstract
Basic properties of tri(4-tert-butylbenzo)[b,g,l](1,2,5-thiadiazolo)[3,4-q]porphyrazine and its Cu complex in the H2SO4-CH3COOH medium were studied by means of spectrophotometric titration. It was found that in going from an acetic acid solution 100% H2SO4 the complete acid-base interaction consecutively involves all the four meso-nitrogen atoms of the porphyrazine macroring, as well as one of the nitrogen atoms of the 1,2,5-thiadiazol fragment. The stability constants of the resulting acid forms were determined and compared with the gas-phase proton affinities calculated by the AM1 method. Annulation of a 1,2,5-thiadiazole fragment to the porphyrazine macroring increases the basicity of the 1,2,5-thiadiazole nitrogen atoms and decreases the basicity of macroring meso-nitrogen atoms.
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Original Russian Text © A.A. Gaberkorn, I.A. Popkova, P.A. Stuzhin, C. Ercolani, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 9, pp. 1558–1568.
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Gaberkorn, A.A., Popkova, I.A., Stuzhin, P.A. et al. Study of basic properties of tert-butyl-substituted tribenzo(1,2,5-thiadiazolo)porphyrazines. Russ J Gen Chem 76, 1494–1503 (2006). https://doi.org/10.1134/S1070363206090222
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DOI: https://doi.org/10.1134/S1070363206090222