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
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 w...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2020-01-01
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| Series: | Journal of the Serbian Chemical Society |
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| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2020/0352-51392000060S.pdf |
| _version_ | 1819240861966270464 |
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| author | Stanić Petar B. Rodić Marko V. Soldatović Tanja V. Pavić Aleksandar B. Radaković Nataša S. Šmit Biljana M. Živković Marija D. |
| author_facet | Stanić Petar B. Rodić Marko V. Soldatović Tanja V. Pavić Aleksandar B. Radaković Nataša S. Šmit Biljana M. Živković Marija D. |
| author_sort | Stanić Petar B. |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-23T14:14:45Z |
| format | Article |
| id | doaj.art-3d14b9c3c0b94b4c828cafb331256bca |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-23T14:14:45Z |
| publishDate | 2020-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-3d14b9c3c0b94b4c828cafb331256bca2022-12-21T17:43:57ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212020-01-0185121591160310.2298/JSC200917060S0352-51392000060SReaction 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)]2Stanić Petar B.0Rodić Marko V.1Soldatović Tanja V.2Pavić Aleksandar B.3Radaković Nataša S.4Šmit Biljana M.5Živković Marija D.6University of Kragujevac, Faculty of Science, Department of Chemistry, Kragujevac, SerbiaUniversity of Novi Sad, Faculty of Sciences, Novi Sad, SerbiaState University of Novi Pazar, Department of Chemical-Technological Sciences, Novi Pazar, SerbiaUniversity of Belgrade, Institute of Molecular Genetics and Genetic Engineering, Belgrade, SerbiaUniversity of Belgrade, Institute of Molecular Genetics and Genetic Engineering, Belgrade, SerbiaUniversity of Kragujevac, Institute for Information Technologies, Department of Science, Kragujevac, SerbiaUniversity of Kragujevac, Faculty of Medical Sciences, Department of Pharmacy, Kragujevac, SerbiaThe 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.http://www.doiserbia.nb.rs/img/doi/0352-5139/2020/0352-51392000060S.pdfcu(ii) complexspectroscopic characterizationsingle crystal x-ray analysisantimicrobial activity |
| spellingShingle | Stanić Petar B. Rodić Marko V. Soldatović Tanja V. Pavić Aleksandar B. Radaković Nataša S. Šmit Biljana M. Živković Marija D. 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 Journal of the Serbian Chemical Society cu(ii) complex spectroscopic characterization single crystal x-ray analysis antimicrobial activity |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | cu(ii) complex spectroscopic characterization single crystal x-ray analysis antimicrobial activity |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2020/0352-51392000060S.pdf |
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