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Investigation of unsubstituted porphyrazine by proton NMR and the structure of porphyrazine ligands

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The proton NMR spectra of unsubstituted porphyrazine (tetraazaporphine) and of its Zn complex in pyridine-D5 and in CF3COOD have been obtained for the first time. The observed strong deshielding of the pyrrole hydrogen atoms of these compounds compared with porphyrins indicates the existence of strong intramolecular hydrogen bonds with neighboring pyrrolenic nitrogen atoms. An unsymmetrical bridge structure is proposed for the reaction center of unsubstituted porphyrazine with significantly ionized N−H bonds. It is suggested that a symmetrical bridge structure almost completely ionized, may exist only in the presence of such strong electron-accepting substituents as halogen in the pyrrole rings of the porphyrazine macrocycle.

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  1. P. A. Stuzhin
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Ivanovo State Instute of Chemical Technology, Ivanovo 153460. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1364–1370, October, 1997.

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Stuzhin, P.A. Investigation of unsubstituted porphyrazine by proton NMR and the structure of porphyrazine ligands. Chem Heterocycl Compd 33, 1185–1190 (1997). https://doi.org/10.1007/BF02290867

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  • DOI: https://doi.org/10.1007/BF02290867

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