Thiazyl trifluoride

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Thiazyl trifluoride - Wikipedia

From Wikipedia, the free encyclopedia

Thiazyl trifluoride

Names

IUPAC name

Thiazyl trifluoride

Other names

Sulfur(VI) nitride trifluoride
Trifluorosulfanenitrile^[1]

Identifiers

CAS Number

15930-75-3^N

3D model (JSmol)

Interactive image

ChEBI

CHEBI:30507^Y

ChemSpider

123471^Y

PubChem CID

140008

CompTox Dashboard (EPA)

DTXSID30166628

InChI

InChI=1S/F3NS/c1-5(2,3)4^Y
Key: UQUPGRNSXINWBS-UHFFFAOYSA-N^Y
InChI=1/F3NS/c1-5(2,3)4
Key: UQUPGRNSXINWBS-UHFFFAOYAR

SMILES

FS(F)(F)#N

Properties

Chemical formula

NSF₃

Molar mass

103.06 g·mol⁻¹

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

sp³

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

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.^[2] 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.^[3]

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:^[4]

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

It is also a product of the oxidation of ammonia by S₂F₁₀.^[5]

Direct fluorination of mercury difluorosulfinimide (Hg(NSF₂)₂) does not give thiazyl trifluoride, but instead the isomeric fluoriminosulfur difluoride (F₂SNF).^[6]

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.^[7] However, the fluoride ligands are labile, and can be displaced by secondary amines.^[6] Thiazyl trifluoride reacts with carbonyl fluoride (COF₂) in the presence of hydrogen fluoride to form pentafluorosulfanyl isocyanate (SF₅NCO).^[8]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ Steve Mitchell (1996). Steve Mitchell (ed.). Biological interactions of sulfur compounds. CRC Press. p. 14. ISBN 0-7484-0245-4.
^ ^a ^b 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.
^ 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.
^ 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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