Thiocyanogen

Thiocyanogen
Names
Preferred IUPAC name
Cyanic dithioperoxyanhydride
Other names
Dicyanodisulfane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C2N2S2/c3-1-5-6-2-4 checkY
    Key: DTMHTVJOHYTUHE-UHFFFAOYSA-N checkY
  • InChI=1/C2N2S2/c3-1-5-6-2-4
    Key: DTMHTVJOHYTUHE-UHFFFAOYAE
  • N#CSSC#N
Properties
C2N2S2
Molar mass 116.16 g mol−1
Appearance Colorless crystal or liquid[1]: 241, 255–256 
Melting point −2.5 °C (27.5 °F; 270.6 K)[1]: 241 
Boiling point ≈20 °C (decomposes)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Thiocyanogen, (SCN)2, is a pseudohalogen derived from the pseudohalide thiocyanate, [SCN], with behavior intermediate between dibromine and diiodine.[2] This hexatomic compound exhibits C2 point group symmetry and has the connectivity NCS-SCN.[3]

In the lungs, lactoperoxidase may oxidize thiocyanate to thiocyanogen[4] or hypothiocyanite.[5]

  1. ^ a b Cite error: The named reference OrgReact was invoked but never defined (see the help page).
  2. ^ a b Schwan, Adrian L. (2001-04-15), "Thiocyanogen", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rt095, ISBN 978-0-471-93623-7, retrieved 2024-03-30
  3. ^ Jensen, James (2005). "Vibrational frequencies and structural determination of thiocyanogen". Journal of Molecular Structure: THEOCHEM. 714 (2–3): 137–141. doi:10.1016/j.theochem.2004.09.046.
  4. ^ Aune, Thomas M.; Thomas, Edwin L. (1977) [2 May 1977]. "Accumulation of hypothiocyanite ion during peroxidase-catalyzed oxidation of thiocyanate ion". European Journal of Biochemistry. 80: 209–214. doi:10.1111/j.1432-1033.1977.tb11873.x.
  5. ^ Lemma, Kelemu; Ashby, Michael T. (2009-09-21). "Reactive Sulfur Species: Kinetics and Mechanism of the Reaction of Hypothiocyanous Acid with Cyanide To Give Dicyanosulfide in Aqueous Solution". Chemical Research in Toxicology. 22 (9): 1622–1628. doi:10.1021/tx900212r. ISSN 0893-228X.