Porphyrin acidity and metal ion coordination revisited: electronic substitution effects |
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| Authors: | Svetlana G Pukhovskaya Dao Tkhe Nam Yulia B Ivanova Lizaveta S Liulkovich Alexander S Semeikin Sergei A Syrbu Mikalai M Kruk |
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| Institution: | 1.Ivanovo State University of Chemistry and Technology,Ivanovo,Russian Federation;2.G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences,Ivanovo,Russian Federation;3.Belarusian State Technological University,Minsk,Belarus |
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| Abstract: | Macrocycle acidity and Zn2+ ion coordination are reported for three porphyrin derivatives which differ in both steric and electronic substitution effects on the macrocycle π-conjugated system. The role of the electronic substitution effects in the macrocycle deprotonation and metal ion chelating was found to be dominating whereas the macrocycle nonplanar distortions contribute to the acidity and metal chelation rate of the studied porphyrins in less extent. The contributions of both resonance and inductive electronic substitution effects have been distinguished based on the relationship between the weighted sum of resonance and inductive Hammett constants and the acidity and metal ion chelation rate. |
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