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| ImageFileR1 = Thiazyl-trifluoride-3D-vdW.png | ImageFileR1 = Thiazyl-trifluoride-3D-vdW.png
| IUPACName = Thiazyl trifluoride | IUPACName = Thiazyl trifluoride
| OtherNames = Sulfur(VI) nitride trifluoride<br />Trifluorosulfanenitrile<ref>{{Cite journal |last=Li |first=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}}</ref> | OtherNames = Sulfur(VI) nitride trifluoride<br />Trifluorosulfanenitrile<ref>{{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}}</ref>
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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==Reactions== ==Reactions==
{{chem2|NSF3}} is much more stable than thiazyl fluoride, does not react with ] and ], and only reacts with ] at 400 °C.<ref>{{cite book | last=Huheey | first=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}}</ref> However, the fluoride ligands are labile, and can be displaced by ]s.<ref name=Sulf>{{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.&nbsp;W.|last=Roesky|chapter=The Sulfur&ndash;Nitrogen Bond|pp=29}}</ref> Thiazyl trifluoride reacts with ] ({{chem2|COF2}}) in the presence of ] to form pentafluorosulfanyl isocyanate ({{chem2|SF5NCO}}).<ref>{{ cite patent {{chem2|NSF3}} is much more stable than thiazyl fluoride, does not react with ] and ], and only reacts with ] at 400 °C.<ref>{{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}}</ref> However, the fluoride ligands are labile, and can be displaced by ]s.<ref name=Sulf>{{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.&nbsp;W.|last=Roesky|chapter=The Sulfur&ndash;Nitrogen Bond|pages=29}}</ref> Thiazyl trifluoride reacts with ] ({{chem2|COF2}}) in the presence of ] to form pentafluorosulfanyl isocyanate ({{chem2|SF5NCO}}).<ref>{{ cite patent
| country = US | country = US
| number = 3,666,784 | number = 3,666,784

Latest revision as of 17:12, 5 November 2024

Thiazyl trifluoride
Names
IUPAC name Thiazyl trifluoride
Other names Sulfur(VI) nitride trifluoride
Trifluorosulfanenitrile
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/F3NS/c1-5(2,3)4Key: UQUPGRNSXINWBS-UHFFFAOYSA-N
  • InChI=1/F3NS/c1-5(2,3)4Key: UQUPGRNSXINWBS-UHFFFAOYAR
SMILES
  • FS(F)(F)#N
Properties
Chemical formula NSF3
Molar mass 103.06 g·mol
Appearance Colourless gas
Melting point −72.6 °C (−98.7 °F; 200.6 K)
Boiling point −27.1 °C (−16.8 °F; 246.1 K)
Structure
Molecular shape Tetrahedral at the S atom
Hybridisation sp
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Thiazyl trifluoride is a chemical compound of nitrogen, sulfur, and fluorine, having the formula NSF3. It exists as a stable, colourless gas, and is an important precursor to other sulfur-nitrogen-fluorine compounds. 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.

Preparation

NSF3 can be synthesised by the fluorination of thiazyl fluoride, NSF, with silver(II) fluoride, AgF2:

NSF + 2 AgF2 → NSF3 + 2 AgF

or by the oxidative decomposition of FC(O)NSF2 by silver(II) fluoride:

FC(O)NSF2 + 2 AgF2 → NSF3 + 2 AgF + COF2

It is also a product of the oxidation of ammonia by S2F10.

Direct fluorination of mercury difluorosulfinimide (Hg(NSF2)2) does not give thiazyl trifluoride, but instead the isomeric fluoriminosulfur difluoride (F2SNF).

Reactions

NSF3 is much more stable than thiazyl fluoride, does not react with ammonia and hydrogen chloride, and only reacts with sodium at 400 °C. However, the fluoride ligands are labile, and can be displaced by secondary amines. Thiazyl trifluoride reacts with carbonyl fluoride (COF2) in the presence of hydrogen fluoride to form pentafluorosulfanyl isocyanate (SF5NCO).

References

  1. Li, Bing-Yu; Su, Kexin; Van Meervelt, Luc; Verhelst, Steven H. L.; Ismalaj, Ermal; De Borggraeve, Wim M.; Demaerel, Joachim (2023-07-17). "Ex situ Generation of Thiazyl Trifluoride (NSF 3 ) as a Gaseous SuFEx Hub**" (PDF). Angewandte Chemie International Edition. 62 (29). doi:10.1002/anie.202305093. ISSN 1433-7851.
  2. Oskar Glemser and Rüdiger Mews (1980). "Chemistry of Thiazyl Fluoride (NSF) and Thiazyl Trifluoride (NSF3): A Quarter Century of Sulfur-Nitrogen-Fluorine Chemistry". Angew. Chem. Int. Ed. Engl. 19 (11): 883–899. doi:10.1002/anie.198008831.
  3. Borrmann, T.; Lork, E.; Mews, R. D.; Parsons, S.; Petersen, J.; Stohrer, W. D.; Watson, P. G. (2008). "The crystal structures of NSF
    3 and (NSF2N(CH3)CH2–)2: How short is the 'Crystallographic' N≡S triple bond?". Inorganica Chimica Acta. 361 (2): 479–486. doi:10.1016/j.ica.2007.05.016.
  4. Chivers, Tristram; Laitinen, Risto S. (2006). "Chalcogen–Nitrogen Chemistry". In Devillanova, Francesco (ed.). Handbook of Chalcogen Chemistry. London: The Royal Society of Chemistry. p. 238. doi:10.1039/9781847557575. ISBN 978-0-85404-366-8.
  5. Steve Mitchell (1996). Steve Mitchell (ed.). Biological interactions of sulfur compounds. CRC Press. p. 14. ISBN 0-7484-0245-4.
  6. ^ Roesky, H. W. (1971). "The Sulfur–Nitrogen Bond". In Senning, Alexander (ed.). Sulfur in Organic and Inorganic Chemistry. Vol. 1. New York: Marcel Dekker. p. 29. ISBN 0-8247-1615-9. LCCN 70-154612.
  7. Huheey, James E.; Keiter, Ellen A.; Keiter, Richard L. (2003). Anorganische Chemie (in German). Berlin: Walter de Gruyter. p. 1021. ISBN 978-3-11-017903-3.
  8. US patent 3,666,784, Alan F. Clifford, Thomas C. Rhyne and James W. Thompson, "Process For Preparing .alpha.,.alpha.-Fluorinated Alkyl Isocyanates", issued 1972-05-30 
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