Thioformamide

Last updated
Thioformamide
HCSNH2.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.694 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-063-7
PubChem CID
UNII
  • InChI=1S/CH3NS/c2-1-3/h1H,(H2,2,3)
    Key: CYEBJEDOHLIWNP-UHFFFAOYSA-N
  • C(=S)N
Properties
CH3NS
Molar mass 61.10 g·mol−1
Appearancewhite solid
Density 1.261 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thioformamide is the organosulfur compound with the formula HC(S)NH2. Although lightly studied, it is of interest as the parent thioamide. The structure has been confirmed by X-ray crystallography, which reveals the expected planar structure with a C=S bond (167 picometer). [1]

The compound is prepared by treating formamide with phosphorus pentasulfide. [1]

As a component of the cyanosulfidic protometabolism hypothesis, thioformamide and related compounds have been implicated as prebiotic precursors to peptides. [2]

References

  1. 1 2 Bernhardt, Bastian; Dressler, Friedemann; Eckhardt, André K.; Becker, Jonathan; Schreiner, Peter R. (2021). "Characterization of the Simplest Thiolimine: The Higher Energy Tautomer of Thioformamide". Chemistry – A European Journal. 27 (22): 6732–6739. Bibcode:2021ChEuJ..27.6732B. doi:10.1002/chem.202005188. PMC   8252572 . PMID   33496350.
  2. ↑ Patel, Bhavesh H.; Percivalle, Claudia; Ritson, Dougal J.; Duffy, Colm D.; Sutherland, John D. (2015). "Common origins of RNA, protein and lipid precursors in a cyanosulfidic protometabolism". Nature Chemistry. 7 (4): 301–307. Bibcode:2015NatCh...7..301P. doi:10.1038/nchem.2202. PMC   4568310 . PMID   25803468.
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