Intra- and intermolecular hydrogen bonding in N,N'-Carbonyl bis(carbamates), -(S-thiocarbamates) and N,N'-biscarbamoyl ureas

The three structural related compound classes of N,N'-biscarbamoyl ureas, N,N'-carbonyl bis(carbamates) and N,N'-carbonyl bis(S-thiocarbamates) have been intensively studied. 13C NMR spectroscopy shows a specific chemical shift for each compound class. In the solid state the molecules undergo intramolecular ring formation and additionally intermolecular dimer or strand building both via hydrogen bonds. The influence of the organic groups is showcased by Hirshfeld surface analysis and the study is rounded off by findings from IR spectroscopy.