Sulfonyl Diazide
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Sulfuryl diazide or sulfuryl azide is a chemical compound with the molecular formula . It was first described in the 1920s when its reactions with
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
and ''p''-xylene were studied by
Theodor Curtius ''Geheimrat'' Julius Wilhelm Theodor Curtius (27 May 1857 – 8 February 1928) was professor of Chemistry at Heidelberg University and elsewhere. He published the Curtius rearrangement in 1890/1894 and also discovered diazoacetic acid, hydra ...
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 Infrared (IR), sometimes called infrared light, is electromagnetic radiation (EMR) with wavelengths longer than those of visible light. It is therefore invisible to the human eye. IR is generally understood to encompass wavelengths from around ...
and Raman spectroscopy; its structure in the solid state was determined by
x-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
. Its melting point is -15 °C. It was prepared by the reaction of
sulfuryl chloride Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis. Sulfuryl chloride is ...
() with sodium azide () using acetonitrile as solvent: : Sulfuryl diazide has been used as a reagent to perform reactions that remove nitrogen from heterocyclic compounds: :


See also

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Trifluoromethanesulfonyl azide Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis. Preparation Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfoni ...


References

{{Azides Azido compounds Sulfuryl compounds Substances discovered in the 1920s