Reaction of diacetylmonoxime with morpholine N-thiohydrazide in the absence and in presence of a metal ion: Facile synthesis of a thiadiazole derivative with non-bonded S S interaction |
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Authors: | Susobhan Biswas Glenn PA Yap Kamalendu Dey |
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Institution: | aDepartment of Chemistry, University of Kalyani, Kalyani 741235, India;bDepartment of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA |
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Abstract: | The condensation of diacetylmonoxime (damnx) with morpholine N-thiohydrazide (mth) in 1:1 molar ratio in ethanol (16 h) afforded a nitrogen–sulfur zwitterionic heterocyclic compound, N-(3,4-dimethyl-1,2,5-thiadiazole-2-ium-2-yl)morpholine-4-carbothioate (dtmc). However, the same reaction in presence of Zn(OAc)2]·2H2O in ethanol under gentle reflux on (3 h) yielded the zinc complex, Zn(Hdammthiol)(OAc)(H2O)]·H2O, where H2dammthiol (H2L2) is the thiol form of tridentate NNS donor thiohydrazone ligand, diacetylmonoxime morpholine N-thiohydrazone (Hdammth). Both the nitrogen–sulfur heterocyclic compound and the zinc complex have been characterized by elemental analyses, spectroscopy (IR, UV–Vis, 1H NMR and 13C NMR) and single crystal X-ray crystallography. It is noteworthy that the heterocyclic compound shows S S interaction with distance 2.738 Å in its planar conformation. The heterocyclic compound forms two dimensional supramolecular sheets through C–H O and π π interactions while the zinc complex, with distorted square pyramidal geometry, forms 1D supramolecular chain. A mechanism has been proposed for the formation of nitrogen–sulfur heterocyclic compound. |
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Keywords: | Thiadiazole Thiohydrazone ligand π sciencedirect com/scidirimg/entities/22ef gif" alt="cdots three dots centered" title="cdots three dots π" target="_blank">centered" border="0">π interactions S sciencedirect com/scidirimg/entities/22ef gif" alt="cdots three dots centered" title="cdots three dots S interaction" target="_blank">centered" border="0">S interaction Supramolecular chemistry Photoluminescence |
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