Misplaced Pages

Thiocyanuric acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Thiocyanuric acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.294 Edit this at Wikidata
EC Number
  • 211-322-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H3N3S3/c7-1-4-2(8)6-3(9)5-1/h(H3,4,5,6,7,8,9)Key: WZRRRFSJFQTGGB-UHFFFAOYSA-N
SMILES
  • C1(=S)NC(=S)NC(=S)N1
Properties
Chemical formula C3H3N3S3
Molar mass 177.26 g·mol
Appearance yellow solid
Density 135 g/cm
Melting point 290 °C (554 °F; 563 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302
Precautionary statements P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Thiocyanuric acid is the organosulfur compound with the formula (HNC=S)3. It is analogous to cyanuric acid ((HNC=O)3). Cyanuric acid is white whereas thiocyanuric acid is yellow. It can also be viewed as a trimeric thioamide.

Structure

It is a planar molecular as determined by X-ray crystallography. Like cyanuric acid, thiocyanuric acid forms extended hydrogen-bonded network resulting in a sheet-like structure. This arrangement is relevant to the high melting point of the compound.

Synthesis, reactions, applications

Thiocyanuric acid precipitates from warm, acidic solutions of thiocyanic acid. A modern synthesis begins instead with a preformed ring: cyanuric chloride reacts with sodium hydrosulfide to give table salt and thiocyanuric acid.

The compound is mildly acidic, with pKa's of 5.7, 8.4, and 11.4. Various salts of (HNC=S)−3 have been characterized.

The compound has an affinity for heavy metals. This attribute has been exploited by applying thiocyanuric acid and derivatives to treatment of waste waters.

References

  1. "Trithiocyanuric acid". pubchem.ncbi.nlm.nih.gov.
  2. Brito, Iván; Albanez, Joselyn; Bolte, Michael (2010). "Trithiacyanuric acid: A second triclinic polymorph". Acta Crystallographica Section E: Structure Reports Online. 66 (9): o2382 – o2383. Bibcode:2010AcCrE..66o2382B. doi:10.1107/S1600536810033234. PMC 3007918. PMID 21588719.
  3. ^ Henke, Kevin R.; Hutchison, Aaron R.; Krepps, Matthew K.; Parkin, Sean; Atwood, David A. (2001). "Chemistry of 2,4,6-Trimercapto-1,3,5-triazine (TMT): Acid Dissociation Constants and Group 2 Complexes". Inorganic Chemistry. 40 (17): 4443–4447. doi:10.1021/ic0103188. PMID 11487353.
  4. Dean, Philip A. W.; Jennings, Michael; Houle, Teena M.; Craig, Donald C.; Dance, Ian G.; Hook, James M.; Scudder, Marcia L. (2004). "Crystal packing in tetraphenylphosphonium salts of trithiocyanuric acid and its methanol solvate". CrystEngComm. 6 (88): 543. doi:10.1039/b413145b.
  5. Pohl, Alina (2020). "Removal of Heavy Metal Ions from Water and Wastewaters by Sulfur-Containing Precipitation Agents". Water, Air, & Soil Pollution. 231 (10): 503. Bibcode:2020WASP..231..503P. doi:10.1007/s11270-020-04863-w.
Categories: