Sulfuryl diazide

Sulfuryl diazide
Names
IUPAC name
Sulfuryl diazide
Other names
Sulfuryl azide; Sulfonyl diazide
Identifiers
CAS Number
  • 72250-07-8
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10606313
PubChem CID
  • 15191028
CompTox Dashboard (EPA)
  • DTXSID401336969 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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
Chemical compound

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.[1][2][3] The compound is reported as having "exceedingly explosive, unpredictable properties" and "in many cases very violent explosions occurred without any apparent reason".[1]

It was not until 2011 that sulfuryl diazide was isolated in a pure enough state to be fully characterized.[4] It was characterized by infrared and Raman spectroscopy; its structure in the solid state was determined by x-ray crystallography.[4] Its melting point is -15 °C.[4] 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:[5][6][7]

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

See also

References

  1. ^ a b Curtius, Theodor; Schmidt, Friedrich (1922). "Action of sulfuryl azide, N3SO2N3, on p-xylene". Berichte der Deutschen Chemischen Gesellschaft B. 55B: 1571–1581.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Schmidt, Friedrich (1922). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft B. 55B: 1581–1583. doi:10.1002/cber.19220550611.
  3. ^ Schmidt, K. F. (1925). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft B. 58B: 2409–2412. doi:10.1002/cber.19250581027.
  4. ^ a b c Xiaoqing Zeng, Helmut Beckers, Eduard Bernhardt, and Helge Willner (2011). "Synthesis and Characterization of Sulfuryl Diazide, O2S(N3)2". Inorg. Chem. 50 (17): 8679–8684. doi:10.1021/ic201294b. PMID 21815651.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Xiaodong Zou, Jiaqi Zou, Lizheng Yang, Guigen Li, and Hongjian Lu (2017). "Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study". J. Org. Chem. 82 (9): 4677–4688. doi:10.1021/acs.joc.7b00308. PMID 28414236.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Derek Lowe (July 7, 2021). "Carving Out Nitrogens: Pick Your Conditions". In The Pipeline. Science Translational Medicine. Archived from the original on June 5, 2023. Retrieved June 5, 2023.
  7. ^ Qin, Haitao; Cai, Wangshui; Wang, Shuang; Guo, Ting; Li, Guigen; Lu, Hongjian (2021). "N-Atom Deletion in Nitrogen Heterocycles". Angewandte Chemie International Edition. 60 (38): 20678–20683. doi:10.1002/anie.202107356. PMID 34227207. S2CID 235746021.
  • v
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Salts and covalent derivatives of the azide ion
HN3 He
LiN3 Be(N3)2 B(N3)3 CH3N3
C(N3)4
CO(N3)2 		NH4N3
N3NO
N(N3)3
H2N–N3 		O FN3 Ne
NaN3 Mg(N3)2 Al(N3)3 Si(N3)4 P SO2(N3)2 ClN3 Ar
KN3 Ca(N3)2 Sc(N3)3 Ti(N3)4 VO(N3)3 Cr(N3)3
CrO2(N3)2 		Mn(N3)2 Fe(N3)2
Fe(N3)3 		Co(N3)2
Co(N3)3 		Ni(N3)2 CuN3
Cu(N3)2 		Zn(N3)2 Ga(N3)3 Ge As(N3)5 Se(N3)4 BrN3 Kr
RbN3 Sr(N3)2 Y(N3)3 Zr(N3)4 Nb Mo Tc Ru(N3)63− Rh(N3)63− Pd(N3)2 AgN3 Cd(N3)2 In Sn Sb(N3)5 Te(N3)4 IN3 Xe(N3)2
CsN3 Ba(N3)2 * Lu(N3)3 Hf Ta W Re Os Ir(N3)63− Pt(N3)62− Au(N3)4− Hg2(N3)2
Hg(N3)2 		TlN3 Pb(N3)2 Bi(N3)3 Po At Rn
Fr Ra(N3)2 ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* La(N3)3 Ce(N3)3
Ce(N3)4 		Pr Nd Pm Sm(N3)3 Eu(N3)2
Eu(N3)3 		Gd(N3)3 Tb Dy(N3)3 Ho(N3)3 Er Tm Yb(N3)3
** Ac(N3)3 Th(N3)4 Pa UO2(N3)2 Np Pu Am Cm Bk Cf Es Fm Md No