A Selective Chromogenic Probe for Mercury(II) and Cyanide in Aqueous Buffered Solution from a Cycloaddition Reaction of an Ynamine to Polycyclic Dithiolethiones

The synthesis of some new polysulfur-nitrogen heterocycles by cycloaddition of an ynamine to bisdithiolothiazine ketothiones or dithiones is described and the interconversion between regioisomers is studied by DFT calculations, showing that the double bond isomerizes at room temperature. This series is a new selective and sensitive chromogenic probe for the naked-eye detection of mercury(II) cation and cyanide anion in buffered (HEPES 0.05M, pH 7.14) water/acetonitrile 1:1 mixture, with sub-micromolar sensitivity, and constitutes the first example of a new class of colorimetric chemical probes for Hg2+ and CN-.