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Meso tetrakis ortho-, meta-, and para-N-alkylpyridiniopor-phyrins: kinetics of copper(II) and zinc(II) incorporation and zinc porphyrin demetalation

Peter Hambright

Department of Chemistry, Howard University, Washington, DC 20059, USA

Corresponding author, fax: +1 202-806-6911.

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Ines Batinić-Haberle

Department of Biochemistry, Duke University Medical Center, Durham, NC 27710, USA

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, and

Ivan Spasojević

Department of Biochemistry, Duke University Medical Center, Durham, NC 27710, USA

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https://doi.org/10.1142/S1088424603000197Cited by:8 (Source: Crossref)

Abstract

The relative reactivities of the tetrakis(N-alkylpyridinium-X-yl)-porphyrins where X = 4 (alkyl = methyl, ethyl, n-propyl), X = 3 (methyl), and X = 2 (methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl) were studied in aqueous solution. From the ionic strength dependence of the metalation rate constants, the effective charge of a particular cationic porphyrin was usually larger when copper(II) rather than zinc(II) was the reactant. The kinetics of ZnOH⁺ incorporation and the acid catalyzed removal of zinc from the porphyrins in 1.0 M HCl were also studied. In general, the more basic 4- (para-) and 3- (meta-) isomers were the most reactive, followed by the less basic 2- (ortho-) methyl to n-butyl derivatives, with the lipophilic ortho n-hexyl and n-octyl porphyrins the least reactive.

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