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International Union of Crystallography, Acta Crystallographica Section C: Structural Chemistry, 6(71), p. 430-434, 2015

DOI: 10.1107/s205322961500813x

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Partial conversion of thioamide into nitrile in a copper(II) complex of 2,6-diacetylpyridine bis(thiosemicarbazone), a drug prototype for Alzheimer's disease

Journal article published in 2015 by Rafael P. Vieira ORCID, John R. Thompson, Heloisa Beraldo ORCID, Tim Storr
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

This work reports the crystal structure of [(Z)-2-((E)-1-{6-[1-({[amino(sulfanidyl-κS)methylidene]amino}imino-κN)ethyl]pyridin-2-yl-κN}ethylidene)-1-cyanohydrazinido-κN1]copper(II), [Cu(C11H11N7S)], the first description of a copper(II) complex of 2,6-diacetylpyridine bis(thiosemicarbazone) showing partial conversion of a thioamide group to a nitrile group. The asymmetric ligand coordinates to the metal centre in anN,N′,N′′,S-tetradentate mannerviathe pyridine N atom, an imine N atom, the hydrazinide N atom and the sulfanidyl S atom, displaying a square-planar geometry. Ligand coordination results in two five-membered chelate rings and one six-membered chelate ring, and in crystal packing based on N—H...N hydrogen bonds of the cyanohydrazinide and hydrazinecarbothioamidate arms of the ligand. The correlation between the partial conversion upon metal complexation, H2S release and possible effects on the activity of bis(thiosemicarbazone)s as drug prototypes for Alzheimer's disease is also discussed.