N—H...S and C—H...S hydrogen bonds in two tetraalkylammonium dithiobiurea(1–) inclusion compounds

Abstract

Two inclusion compounds of dithiobiurea and tetrapropylammonium and tetrabutylammonium are characterized and reported, namely tetrapropylammonium carbamothioyl(carbamothioylamino)azanide, C12H28N+·C2H5N4S2−, (1), and tetrabutylammonium carbamothioyl(carbamothioylamino)azanide, C16H36N+·C2H5N4S2−, (2). The results show that in (1), the dithiobiurea anion forms a dimerviaN—H...N hydrogen bonds and the dimers are connected into wide hydrogen-bonded ribbons. The guest tetrapropylammonium cation changes its character to become the host molecule, generating pseudo-channels containing the aforementioned ribbons by C—H...S contacts, yielding the three-dimensional network structure. In comparison, in (2), the dithiobiurea anions are linkedviaN—H...S interactions, producing one-dimensional chains which pack to generate two-dimensional hydrogen-bonded layers. These layers accommodate the guest tetrabutylammonium cations, resulting in a sandwich-like layer structure with host–guest C—H...S contacts.