Thiocarbamoylbenzimidophenylselenide and -telluride and their reactions with metal ions

Thiocarbamoylbenzimidophenylselenide and -telluride have been prepared from N-[N′,N′-methylphenylamino(thiocarbonyl)]benzimidoyl chloride and the in situ-prepared phenylselenolate or -tellurolate, and their structures have been determined by X-ray diffraction. The air-stable compounds react with metal ions such as HgCl2, PdCl2 or Pd(acetate)2 under cleavage of their CN or C–Se/Te bonds. The decomposition fragments react with the transition metal ions under formation of stable products such as [HgCl(SePh)]∞, (3-methylphenylamino-5-phenyl-1,2,4-dithiazolium)2[HgCl4], [Pd(MePhbtu)2] (HMePhbtu = N-methyl-N-phenyl-N′-benzoylthiourea) or [Pd(MePhtu)4]Cl2 (MePhtu = N-methyl-N-phenylthiourea). The products have been isolated in crystalline form and characterized spectroscopically and by X-ray structure analysis.

Graphical abstractThiocarbamoylbenzimidophenylselenide and -telluride are air-stable compounds, which degrade during reactions with HgCl2, PdCl2 or Pd(OOCCH3)2. Compounds with {SePh}−, {MePhNC(S)NC(Ph)S}+, {MePhNC(S)NH2} and {MePhNC(S)NC(O)Ph}− have been isolated.Figure optionsDownload full-size imageDownload as PowerPoint slide