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Thiocyanic acid

From Wikipedia, the free encyclopedia
Chemical compound (H–S–C≡N)
Thiocyanic acid[1]
Skeletal formula of thiocyanic acid with the explicit hydrogen added
Skeletal formula of thiocyanic acid with the explicit hydrogen added
Spacefill model of thiocyanic acid
Spacefill model of thiocyanic acid
  Carbon, C
  Sulfur, S
  Nitrogen, N
  Hydrogen, H
Names
IUPAC name
Thiocyanic acid[4]
Other names
  • Hydrogen thiocyanate[2]
  • Sulfocyanic acid[3]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.006.672Edit this at Wikidata
EC Number
  • 207-337-4
25178
KEGG
MeSHthiocyanic+acid
UNII
  • InChI=1S/CHNS/c2-1-3/h3H checkY
    Key: ZMZDMBWJUHKJPS-UHFFFAOYSA-N checkY
  • thiocyanic acid: SC#N
  • isothiocyanic acid: N=C=S
Properties
HSCN
Molar mass59.09 g·mol−1
Appearance
  • Colourless liquid[5]
  • Colourless gas, autopolymerizing to white solid[2]
OdorPungent
Density2.04 g/cm3
Melting point
  • 5 °C (oligomers?)[5]
  • −110 °C (monomer?)[6]
Miscible
SolubilitySoluble inethanol,diethyl ether
logP0.429
Vapor pressure4.73 mmHg (631 Pa)[7]
Acidity (pKa)0.926
Basicity (pKb)13.071
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302,H312,H332,H412
P261,P264,P270,P271,P273,P280,P301+P312,P302+P352,P304+P312,P304+P340,P312,P322,P330,P363,P501
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Thiocyanic acid is achemical compound with theformulaHSCN andstructureH−S−C≡N, which exists as atautomer with isothiocyanic acid (H−N=C=S).[8] The isothiocyanic acid tautomer tends to dominate with the compound being about 95% isothiocyanic acid in thevapor phase.[9]

Tautomerism between thiocyanic acid (left) and isothiocyanic acid (right)

It is a moderatelystrong acid,[10] with apKa of 1.1 at 20 °C and extrapolated to zeroionic strength.[11]

One of the thiocyanic acid tautomers, HSCN, is predicted to have atriple bond betweencarbon andnitrogen. Thiocyanic acid has been observed spectroscopically.[12]

Thesalts andesters of thiocyanic acid are known asthiocyanates. The salts are composed of the thiocyanate ion ([SCN]) and a suitable cation (e.g.,potassium thiocyanate, KSCN). The esters of thiocyanic acid have the general structureR−S−C≡N, where R stands for anorganyl group.

Isothiocyanic acid, HNCS, is aLewis acid whose free energy, enthalpy and entropy changes for its 1:1 association with a variety of Lewis bases in carbon tetrachloride solution at 25 °C have been reported.[13]< HNCS acceptor properties are discussed in theECW model. The salts are composed of the thiocyanate ion ([SCN]) and a suitable cation (e.g.,ammonium thiocyanate,[NH4]+[SCN]). Isothiocyanic acid forms isothiocyanatesR−N=C=S, where R stands for anorganyl group.

Thiocyanuric acid is a stable trimer of thiocyanic acid.

Wikimedia Commons has media related toThiocyanic acid.

References

[edit]
  1. ^Merck Index, 11th Edition,9257.
  2. ^ab"Thiocyanic acid".The Merck Index.Royal Society of Chemistry.
  3. ^von Richter, Victor (1922).Organic Chemistry or Chemistry of the Carbon Compounds. Vol. 1. Translated by Spielmann, Percy E.Philadelphia: P. Blakiston's Son & Co. p. 466.
  4. ^"Thiocyanic acid" entry inPubChem (database).
  5. ^abILO andWHO staff. "Thiocyanic acid" safety card.European Commission
  6. ^Birckenbach, Lothar (1942).Forschungen und Fortschritte.18:232–3{{cite journal}}:Missing or empty|title= (help). Ascited inCAS Common Chemistry.
  7. ^Brown, Jay A. (ed.; 2024), "Thiocyanic Acid" inHaz-Map (database).Engineered IT.
  8. ^Holleman, A. F.; Wiberg, E. (2001).Inorganic Chemistry. San Diego: Academic Press.ISBN 0-12-352651-5.
  9. ^Beard, C. I.; Dailey, B. P. (1950)."The Structure and Dipole Moment of Isothiocyanic Acid"(PDF).The Journal of Chemical Physics.18 (11): 1437.Bibcode:1950JChPh..18.1437B.doi:10.1063/1.1747507.hdl:1721.1/4934.
  10. ^Munegumi, Toratane (23 January 2013)."Where is the Border Line between Strong Acids and Weak Acids?".World Journal of Chemical Education.1 (1):12–16.
  11. ^Martell, A. E.; Smith, R. M.; Motelaitis, R. J. (2001).NIST Database 46. Gaithersburg, MD: National Institute of Standards and Technology.
  12. ^Wierzejewska, M.; Mielke, Z. (2001). "Photolysis of Isothiocyanic Acid HNCS in Low-Temperature Matrices. Infrared Detection of HSCN and HSNC Isomers".Chemical Physics Letters.349 (3–4):227–234.Bibcode:2001CPL...349..227W.doi:10.1016/S0009-2614(01)01180-0.
  13. ^Barakat, T. M.; Nelson, Jane; Nelson, S. M.; Pullin, A. D. E. (1969)."Spectra and hydrogen-bonding of characteristics of thiocyanic acid. Part 4.—Association with weak proton acceptors".Trans. Faraday Soc.65:41–51.doi:10.1039/tf9696500041.ISSN 0014-7672.
Molecules
Diatomic








Triatomic
Four
atoms
Five
atoms
Six
atoms
Seven
atoms
Eight
atoms
Nine
atoms
Ten
atoms
or more
Deuterated
molecules
Unconfirmed
Related
Salts and covalent derivatives of thethiocyanate ion
Sulfides and
disulfides
Sulfurhalides
Sulfuroxides
andoxyhalides
Sulfites
Sulfates
Sulfurnitrides
Thiocyanates
Organic compounds
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