Thiazyl trifluoride
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470606415
| ImageFileL1 = Thiazyl-trifluoride-2D-dimensions.png
| ImageSizeL1 = 150px
| ImageFileR1 = Thiazyl-trifluoride-3D-vdW.png
| IUPACName = Thiazyl trifluoride
| OtherNames = Sulfur(VI) nitride trifluoride
Trifluorosulfanenitrile{{Cite journal |last1=Li |first1=Bing-Yu |last2=Su |first2=Kexin |last3=Van Meervelt |first3=Luc |last4=Verhelst |first4=Steven H. L. |last5=Ismalaj |first5=Ermal |last6=De Borggraeve |first6=Wim M. |last7=Demaerel |first7=Joachim |date=2023-07-17 |title=Ex situ Generation of Thiazyl Trifluoride (NSF 3 ) as a Gaseous SuFEx Hub** |url=https://lirias.kuleuven.be/bitstream/20.500.12942/719927/2/NSF3-manuscript-v2.pdf |journal=Angewandte Chemie International Edition |language=en |volume=62 |issue=29 |doi=10.1002/anie.202305093 |issn=1433-7851}}
| Section1 = {{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 123471
|InChI = 1/F3NS/c1-5(2,3)4
|InChIKey = UQUPGRNSXINWBS-UHFFFAOYAR
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/F3NS/c1-5(2,3)4
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = UQUPGRNSXINWBS-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|changed|??}}
|CASNo = 15930-75-3
|PubChem = 140008
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 30507
|SMILES = FS(F)(F)#N
}}
| Section2 = {{Chembox Properties
|Formula = {{chem2|NSF3}}
|N=1|S=1|F=3
|Appearance = Colourless gas
|MeltingPtC = −72.6
|BoilingPtC = −27.1
}}
| Section3 = {{Chembox Structure
|MolShape = Tetrahedral at the S atom
|OrbitalHybridisation = sp3
}}
}}
Thiazyl trifluoride is a chemical compound of nitrogen, sulfur, and fluorine, having the formula {{chem2|NSF3}}. It exists as a stable, colourless gas, and is an important precursor to other sulfur-nitrogen-fluorine compounds.{{cite journal | author = Oskar Glemser and Rüdiger Mews | title = Chemistry of Thiazyl Fluoride (NSF) and Thiazyl Trifluoride (NSF3): A Quarter Century of Sulfur-Nitrogen-Fluorine Chemistry | year = 1980 | journal = Angew. Chem. Int. Ed. Engl. | volume = 19 | issue = 11 | pages = 883–899 | doi = 10.1002/anie.198008831}} It has tetrahedral molecular geometry around the sulfur atom, and is regarded to be a prime example of a compound that has a sulfur-nitrogen triple bond.{{Cite journal | doi = 10.1016/j.ica.2007.05.016 | title = The crystal structures of {{chem|NSF|3}} and (NSF2N(CH3)CH2–)2: How short is the 'Crystallographic' N≡S triple bond? | year = 2008 | last1 = Borrmann | first1 = T. | last2 = Lork | first2 = E. | last3 = Mews | first3 = R. D. | last4 = Parsons | first4 = S. | last5 = Petersen | first5 = J. | last6 = Stohrer | first6 = W. D. | last7 = Watson | first7 = P. G. | journal = Inorganica Chimica Acta | volume = 361 | issue = 2| pages = 479–486}}
Preparation
{{chem2|NSF3}} can be synthesised by the fluorination of thiazyl fluoride, NSF, with silver(II) fluoride, {{chem2|AgF2}}:
:{{chem2|NSF + 2 AgF2 → NSF3 + 2 AgF}}
or by the oxidative decomposition of {{chem2|FC(O)NSF2}} by silver(II) fluoride:{{cite book |last1= Chivers | first1=Tristram|first2= Risto S.|last2= Laitinen |editor= Devillanova, Francesco |title= Handbook of Chalcogen Chemistry |url= https://archive.org/details/handbookchalcoge00devi_741 |url-access= limited |year=2006 |publisher=The Royal Society of Chemistry |location=London |isbn= 978-0-85404-366-8 |doi= 10.1039/9781847557575 |page=[https://archive.org/details/handbookchalcoge00devi_741/page/n256 238] |chapter= Chalcogen–Nitrogen Chemistry }}
:{{chem2|FC(O)NSF2 + 2 AgF2 → NSF3 + 2 AgF + COF2}}
It is also a product of the oxidation of ammonia by disulfur decafluoride.{{cite book
| title = Biological interactions of sulfur compounds
| author = Steve Mitchell
| editor = Steve Mitchell
| publisher = CRC Press
| year = 1996
| isbn = 0-7484-0245-4
| page = 14
}}
Direct fluorination of mercury difluorosulfinimide (Hg(NSF2)2) does not give thiazyl trifluoride, but instead the isomeric fluoriminosulfur difluoride (F2SNF).
Reactions
{{chem2|NSF3}} is much more stable than thiazyl fluoride, does not react with ammonia and hydrogen chloride, and only reacts with sodium at 400 °C.{{cite book | last1=Huheey | first1=James E. | last2=Keiter | first2=Ellen A. | last3=Keiter | first3=Richard L. | title=Anorganische Chemie | publisher=Walter de Gruyter | publication-place=Berlin | date=2003 | isbn=978-3-11-017903-3 | language=de|page=1021}} However, the fluoride ligands are labile, and can be displaced by secondary amines.{{cite book|title=Sulfur in Organic and Inorganic Chemistry|volume=1|editor-first=Alexander|editor-last=Senning|year=1971|publisher=Marcel Dekker|location=New York|lccn=70-154612|isbn=0-8247-1615-9|first=H. W.|last=Roesky|chapter=The Sulfur–Nitrogen Bond|pages=29}} Thiazyl trifluoride reacts with carbonyl fluoride ({{chem2|COF2}}) in the presence of hydrogen fluoride to form pentafluorosulfanyl isocyanate ({{chem2|SF5NCO}}).{{ cite patent
| country = US
| number = 3,666,784
| status = patent
| title = Process For Preparing .alpha.,.alpha.-Fluorinated Alkyl Isocyanates
| gdate = 1972-05-30
| inventor = Alan F. Clifford, Thomas C. Rhyne and James W. Thompson
}}