Thiosemicarbazone

A thiosemicarbazone is an organosulfur compound with the formula H₂NC(S)NHN=CR₂. Many variations exist, including those where some or all of the NH centers are substituted by organic groups. Thiosemicarbazones are usually produced by condensation of a thiosemicarbazide with an aldehyde or ketone:

H₂NC(S)NHNH₂ + O=CR₂ → H₂NC(S)NHN=CR₂ + H₂O

General chemical structure of a thiosemicarbazone

In terms of their chemical structures, the CSN3 core atoms are coplanar.^[1]

Occurrence and applications

Some thiosemicarbazones have medicinal properties, e.g. the antiviral metisazone and the antibiotic thioacetazone. Thiosemicarbazones are also widely used as ligands in coordination chemistry.^[2] The affinity of thiosemicarbazones for metal ions is exploited in controlling iron overload.^[3]