Sulfuryl diazide

Sulfuryl diazide
Names
IUPAC name
Sulfuryl diazide
Other names
Sulfuryl azide; Sulfonyl diazide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/N6O2S/c1-3-5-9(7,8)6-4-2
    Key: HSVFKFNNMLUVEY-UHFFFAOYSA-N
  • [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-]
Properties
SO2(N3)2
Molar mass 148.10 g·mol−1
Melting point −15 °C (5 °F; 258 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sulfuryl diazide or sulfuryl azide is a chemical compound with the molecular formula SO2(N3)2. It was first described in the 1920s when its reactions with benzene and p-xylene were studied by Theodor Curtius and Karl Friedrich Schmidt. The compound is reported as having "exceedingly explosive, unpredictable properties" and "in many cases very violent explosions occurred without any apparent reason".

It was not until 2011 that sulfuryl diazide was isolated in a pure enough state to be fully characterized. It was characterized by infrared and Raman spectroscopy; its structure in the solid state was determined by x-ray crystallography. Its melting point is -15 °C. It was prepared by the reaction of sulfuryl chloride (SO2Cl2) with sodium azide (NaN3) using acetonitrile as solvent:

SO2Cl2 + 2 NaN3 → SO2(N3)2 + 2 NaCl

Sulfuryl diazide has been used as a reagent to perform reactions that remove nitrogen from heterocyclic compounds:

R1−NH−R2 + SO2(N3)2 → R1−R2 + SO2 + 2 N2 + HN3
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