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.
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3D model (JSmol)
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| ECHA InfoCard | 100.010.294 |
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CompTox Dashboard (EPA)
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| Properties | |
| C3H3N3S3 | |
| Molar mass | 177.26 g·mol−1 |
| Appearance | yellow solid |
| Density | 135 g/cm3 |
| Melting point | 290 °C (554 °F; 563 K) |
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| H302 | |
| 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 [77 °F], 100 kPa).
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Structure
editIt 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.[2]
Synthesis, reactions, applications
editA modern synthesis begins with cyanuric chloride and a source of hydrosulfide.[3]
The compound is mildly acidic, with pKa's of 5.7, 8.4, and 11.4.[3] Various salts of (HNC=S)−3 have been characterized.[4]
The compound has an affinity for heavy metals. This attribute has been exploited by applying thiocyanuric acid and derivatives to treatment of waste waters.[5]
References
edit- ^ "Trithiocyanuric acid". pubchem.ncbi.nlm.nih.gov.
- ^ 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.
- ^ a b 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.
- ^ 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.
- ^ 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.