Synthesis, crystal and molecular structure, and spectroscopic characterization of 5-(1-hydroxycyclohexylthio)-1,3,4-thiadiazole-2-thione

Abstract

2,5-Dimercapto-1,3,4-thiadiazole (DMTDA), when dissolved in cyclohexanone, interacts strongly with the solvent and the title monothiohemiacetal (MTH) is formed. MTH has been characterized in the solid state by means of X-ray diffraction, IR spectroscopy and thermogravimetric analysis, and in cyclohexanone solution by means of NMR spectroscopy. The title compound crystallizes in the triclinic space group P1^–(No. 2), with cell dimensions a= 6.481 (1), b= 9.322(1), c= 9.553(1)Å, α= 72.31(1). β= 89.74(1), γ= 80.83(1)° and Z= 2. The structure was solved by direct methods, and least-squares refinement of structural parameters led to a conventional R factor of 0.041 for 1074 independent reflections. In the solid state, MTH easily undergoes decomposition with loss of cyclohexanone.