Thiosemicarbazide is the chemical compound with the formula H₂NC(S)NHNH₂. A white, odorless solid, it is related to

thiourea Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), except that the oxygen atom is replaced by a sulfur atom (as implied by the ''thio-'' prefix); however, the properties of urea a ...

(H₂NC(S)NH₂) by the insertion of an NH center. They are commonly used as

ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...

s for transition metals. Many thiosemicarbazides are known. These feature an organic substituent in place of one or more H's of the parent molecule. 4-Methyl-3-thiosemicarbazide is a simple example. According to

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...

, the CSN₃ core of the molecule is planar as are the three H's nearest the

thiocarbonyl In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structu ...

group.

Reactions

Thiosemicarbazides are precursors to

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 N''H'' centers are substituted by organic groups. Thiosemicarbazones are usually produced by condens ...

s. They are precursors to

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

s. Formylation of thiosemicarbazide provides access to triazole.

References

{{Authority control Thiosemicarbazone Functional groups