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Reaction of a 3-aryilidene-2-thiohydantoin derivative with polymeric trans-[CuCl2(DMSO)2]n complex: Unexpected isomerization to dinuclear cis-[{CuCl(DMSO)2}(μ-Cl)]2

Stanić Petar B. (University of Kragujevac, Faculty of Science, Department of Chemistry, Kragujevac, Serbia)
Rodić Marko V. (University of Novi Sad, Faculty of Sciences, Novi Sad, Serbia)
Soldatović Tanja V. (State University of Novi Pazar, Department of Chemical-Technological Sciences, Novi Pazar, Serbia)
Pavić Aleksandar B. (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering, Belgrade, Serbia)
Radaković Nataša S. (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering, Belgrade, Serbia)
Šmit Biljana M. (University of Kragujevac, Institute for Information Technologies, Department of Science, Kragujevac, Serbia), biljana.smit@uni.kg.ac.rs
Živković Marija D. (University of Kragujevac, Faculty of Medical Sciences, Department of Pharmacy, Kragujevac, Serbia), mzivkovic@kg.ac.rs

The 3-arylidene-2-thiohydantoin derivative, 3-[(2-hydroxybenzylidene) amino]-2-thioxoimidazolidin-4-one, was synthesized in a two-step condensation reaction of 2-hydroxybenzaldehyde, thiosemicarbazide and ethyl chloroacetate. The ligand was structurally characterized by NMR and IR spectroscopy, as well as by elemental analysis. In the reaction of the well-known polymeric trans-[CuCl2(DMSO)2]n complex with the polydentate thiohydantoin type ligand, instead of the corresponding copper thiohydantoin complex, unexpectedly, the dinuclear cis-[{CuCl(DMSO)2}(μ-Cl)]2 complex (1) was formed predominantly as the final stable product. The structure of the complex 1 was confirmed by single crystal X-ray diffraction analysis. The cis-complex is obtained through assisted isomerization of the trans-form, in which the thiohydantoin derivative has a crucial role.

Keywords: Cu(II) complex, spectroscopic characterization, single crystal X-ray analysis, antimicrobial activity

Projects of the Serbian Ministry of Education, Science and Technological Development, Grant no. 451-03-68/2020-14/200378 and Grant no. 451-03-68/2020-14/200122