| Revision as of 13:03, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 458212385 of page Thiocyanic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:44, 31 July 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers75,027 edits Thiocyanuric acid is a stable trimer of thiocyanic acid. |
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{{Short description|Chemical compound (H–S–C≡N)}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 418298832 |
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| verifiedrevid = 470607041 |
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| Reference = <ref>'']'', 11th Edition, '''9257'''.</ref> |
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| Reference = <ref>'']'', 11th Edition, '''9257'''.</ref> |
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| ImageFile1 = Thiocyansäure.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Thiocyanic acid.png |
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| ImageName1 = Skeletal formula of thiocyanic acid with the explicit hydrogen added |
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| ImageSize = 150px |
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| ImageFile2 = Thiocyanic-acid-3D-vdW.png |
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| ImageName = Structural formula |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Thiocyanic-acid-3D-vdW.png |
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| ImageName1 = Space-filling model |
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| ImageName2 = Spacefill model of thiocyanic acid |
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| ImageCaption2 = {{legend|black|], C}}{{legend|yellow|], S}}{{legend|blue|], N}}{{legend|white|], H}} |
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| IUPACName = |
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| IUPACName = Thiocyanic acid<ref name=pubchem>"" entry in ] (database).</ref> |
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| OtherNames = Hydrogen thiocyanate; Sulfocyanic acid; Sulfocyanide |
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| OtherNames = {{Unbulleted list|Hydrogen thiocyanate<ref name=Merck/>|Sulfocyanic acid<ref>{{cite book |last=von Richter |first=Victor |translator-last=Spielmann |translator-first=Percy E. |title=Organic Chemistry or Chemistry of the Carbon Compounds |date=1922 |publisher=P. Blakiston's Son & Co. |location=] |volume=1 |page=466 |url=https://books.google.com/books?id=WV0vAQAAMAAJ&pg=PA466}}</ref>}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo = 463-56-9 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = A5KWW7N91V |
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| PubChem = 781 |
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| ChemSpiderID = 760 |
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| ChemSpiderID = 760 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/CHNS/c2-1-3/h3H |
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| EINECS = 207-337-4 |
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| InChIKey = ZMZDMBWJUHKJPS-UHFFFAOYAD |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C01755 |
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| MeSHName = thiocyanic+acid |
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| ChEBI = 29200 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 84336 |
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| ChEMBL = 84336 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Gmelin = 25178 |
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| 3DMet = B00344 |
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| SMILES = SC#N |
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| SMILES_Comment = thiocyanic acid |
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| SMILES1 = N=C=S |
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| SMILES1_Comment = isothiocyanic acid |
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| StdInChI = 1S/CHNS/c2-1-3/h3H |
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| StdInChI = 1S/CHNS/c2-1-3/h3H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZMZDMBWJUHKJPS-UHFFFAOYSA-N |
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| StdInChIKey = ZMZDMBWJUHKJPS-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 463-56-9 |
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|Section2={{Chembox Properties |
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| PubChem = 781 |
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| Formula = HSCN |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| C=1|H=1|N=1|S=1 |
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| ChEBI = 29200 |
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| Appearance = {{ubl|Colourless liquid<ref name=ICSC/>|Colourless gas, autopolymerizing to white solid<ref name=Merck>{{cite Merck Index|monograph_id=m10751|title=Thiocyanic acid}}</ref>}} |
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| SMILES = N#CS |
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| Odor = Pungent |
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| Solubility = Miscible |
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| SolubleOther = Soluble in ], ] |
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| LogP = 0.429 |
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| pKa = 0.926 |
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| pKb = 13.071 |
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| Density = 2.04 g/cm<sup>3</sup> |
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| MeltingPt = {{ubl|5 °C (oligomers?)<ref name=ICSC>] and ] staff. "" safety card. ]</ref>|-110 °C (monomer?)<ref>{{cite journal|last1=Birckenbach|first1=Lothar|year=1942|journal=Forschungen und Fortschritte|volume=18|pages=232–3|postscript=none}}. As in ].</ref>}} |
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| VaporPressure = {{cvt|4.73|mmHg|Pa}}<ref>Brown, Jay A. (ed.; 2024), "" in ] (database). ].</ref> |
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}} |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302|312|332|412}} |
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| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+312|304+340|312|322|330|363|501}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section9={{Chembox Related |
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| OtherCompounds = {{ubl|]|]|]|]|]|]|]|]|]|]|]}} |
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| C=1 | H=1 | N=1 | S=1 |
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| Appearance = |
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| Density = |
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| MeltingPtC = |
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| BoilingPt = |
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| Solubility = Miscible}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = |
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| RPhrases = {{R20/21/22}} {{R32}} {{R52/53}} |
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| SPhrases = {{S2}} {{S13}} {{S61}} |
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'''Thiocyanic acid''' is a ] with the ] {{chem2|HSCN|auto=1}} and ] {{chem2|H\sS\sC\tN}}, which exists as a ] with isothiocyanic acid ({{chem2|H\sN\dC\dS}}).<ref>{{cite book|last1=Holleman |first1=A. F. |last2=Wiberg |first2=E. |title=Inorganic Chemistry |publisher=Academic Press |location=San Diego |date=2001 |isbn=0-12-352651-5}}</ref> The isothiocyanic acid tautomer tends to dominate with the compound being about 95% isothiocyanic acid in the ].<ref>{{cite journal|last1=Beard|first1=C. I.|last2=Dailey|first2=B. P.|title=The Structure and Dipole Moment of Isothiocyanic Acid|journal=]|date=1950|volume=18|issue=11|pages=1437|doi=10.1063/1.1747507|url=https://dspace.mit.edu/bitstream/1721.1/4934/1/RLE-TR-112-04711196.pdf|bibcode=1950JChPh..18.1437B|hdl=1721.1/4934|hdl-access=free}}</ref> |
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:] |
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It is a moderately ],<ref>{{Cite journal|url=http://pubs.sciepub.com/wjce/1/1/4/index.html|title=Where is the Border Line between Strong Acids and Weak Acids?|journal=World Journal of Chemical Education|date=23 January 2013|volume=1|issue=1|pages=12–16|last1=Munegumi|first1=Toratane}}</ref> with a ] of 1.1 at 20 °C and extrapolated to zero ].<ref>{{cite book|last1=Martell |first1=A. E. |last2=Smith |first2=R. M. |last3=Motelaitis |first3=R. J. |title=NIST Database 46 |publisher=National Institute of Standards and Technology |location=Gaithersburg, MD |date=2001}}</ref> |
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One of the thiocyanic acid tautomers, HSCN, is predicted to have a ] between ] and ]. Thiocyanic acid has been observed spectroscopically.<ref>{{cite journal | doi = 10.1016/S0009-2614(01)01180-0 |author1=Wierzejewska, M. |author2=Mielke, Z. | title = Photolysis of Isothiocyanic Acid HNCS in Low-Temperature Matrices. Infrared Detection of HSCN and HSNC Isomers | journal = ] | year = 2001 | volume = 349 |issue=3–4 | pages = 227–234|bibcode=2001CPL...349..227W}}</ref> |
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The ] and ]s of thiocyanic acid are known as ]s. The salts are composed of the thiocyanate ion ({{chem2|−}}) and a suitable cation (e.g., ], KSCN). The esters of thiocyanic acid have the general structure {{chem2|R\sS\sC\tN}}, where R stands for an ] group. |
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Isothiocyanic acid, HNCS, is a ] 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.<ref>{{Cite journal |last1=Barakat |first1=T. M. |last2=Nelson |first2=Jane |last3=Nelson |first3=S. M. |last4=Pullin |first4=A. D. E. |date=1969 |title=Spectra and hydrogen-bonding of characteristics of thiocyanic acid. Part 4.—Association with weak proton acceptors |url=http://dx.doi.org/10.1039/tf9696500041 |journal=Trans. Faraday Soc. |volume=65 |pages=41–51 |doi=10.1039/tf9696500041 |issn=0014-7672}}</ref>< HNCS acceptor properties are discussed in the ]. The salts are composed of the thiocyanate ion ({{chem2|−}}) and a suitable cation (e.g., ], {{chem2|+−}}). Isothiocyanic acid forms isothiocyanates {{chem2|R\sN\dC\dS}}, where R stands for an ] group. |
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] is a stable trimer of thiocyanic acid. |
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{{Commons category}} |
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==References== |
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{{Reflist}} |
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{{Molecules detected in outer space}} |
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{{Thiocyanates}} |
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{{hydrogen compounds}} |
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{{sulfur compounds}} |
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] |
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] |