Thiosemicarbazide Explained

Thiosemicarbazide is the chemical compound with the formula H2NC(S)NHNH2. A white, odorless solid, it is related to thiourea (H2NC(S)NH2) by the insertion of an NH center. They are commonly used as ligands for transition metals.[1] 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, the CSN3 core of the molecule is planar as are the three H's nearest the thiocarbonyl group.[2]

Reactions

Thiosemicarbazides are precursors to thiosemicarbazones. They are precursors to heterocycles.[3] Formylation of thiosemicarbazide provides access to triazole.[4]

Notes and References

  1. 10.1016/S0010-8545(00)80276-3. Transition metal complexes of thiosemicarbazide and thiosemicarbazones. 1975. Campbell. Michel J.M.. Coordination Chemistry Reviews. 15. 2–3. 279–319.
  2. 10.1107/S0567740870003497. Hydrogen bonding in thiosemicarbazide. 1970. Andreetti. G. D.. Domiano. P.. Gasparri. G. F.. Nardelli. M.. Sgarabotto. P.. Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 26. 7. 1005–1009. 1970AcCrB..26.1005A .
  3. 10.1070/RC2012v081n06ABEH004235. Thiosemicarbazides in the synthesis of five- and six-membered heterocyclic compounds. 2012. Gazieva. Galina A.. Kravchenko. Angelina N.. Russian Chemical Reviews. 81. 6. 494–523. 2012RuCRv..81..494G. 96691115 .
  4. 10.15227/orgsyn.040.0099. C. Ainsworth. 1,2,4-Triazole. Organic Syntheses. 1960. 40. 99.

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