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Thiosemicarbazide

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. 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 almost planar as are the three H atoms nearest the thiocarbonyl group. This can be explained by models of electron delocalisation.

Reactions

Thiosemicarbazides are precursors to thiosemicarbazones. They are precursors to heterocycles. Formylation of thiosemicarbazide provides access to triazole.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. (1975). "Transition metal complexes of thiosemicarbazide and thiosemicarbazones". Coordination Chemistry Reviews.
  3. (1970). "Hydrogen bonding in thiosemicarbazide". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry.
  4. (2012). "Thiosemicarbazides in the synthesis of five- and six-membered heterocyclic compounds". Russian Chemical Reviews.
  5. C. Ainsworth. (1960). "1,2,4-Triazole". Organic Syntheses.
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thiosemicarbazones functional-groups semicarbazides
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