Dithiocarbamates, thiocarbamic esters, dithiocarboimidates, guanidines, thioureas, isothioureas, and tetraazathiapentalene derived from 2-aminobenzothiazole

Reactions between CS₂ and the exocyclic amino groups of 2-aminobenzothiazoles gave series of molecules bearing thiourea, isothiourea, dithiocarbamate, dithiocarboimine, dimethyldithiocarbamate, methyldithiocarbamate, S-CH₃ and O-alkyl thiocarbarnic ester, and guanidine groups. Preferred tautomers and conformers were determined. Most compounds present coordinative bonds between the endocyclic sulfur atom, which behaves as a Lewis acid, and oxygen, nitrogen, and sulfur acting as bases. A new dibenzothiazolyltetraazathiapentalene containing a T-shaped hypervalent sulfur atom and displaying "single bond-no bond resonance" is discussed. X-ray structures of eleven compounds are reported.