Chemistry:Sulfuryl diazide
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| Names | |
|---|---|
| IUPAC name
Sulfuryl diazide
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| Other names
Sulfuryl azide; Sulfonyl diazide
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| Properties | |
| SO 2(N 3) 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 SO
2(N
3)
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]
Synthesis
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 (SO
2Cl
2) with sodium azide (NaN
3) using acetonitrile as solvent:
- SO
2Cl
2 + 2 NaN
3 → SO
2(N
3)
2 + 2 NaCl
Physical properties
Sulfuryl diazide is extremely explosive and can explode even without strong external influences. The compound crystallizes in the monoclinic crystal system in the space group C2/c (space group no. 15) with the lattice parameters a = 24.3405 Å; b = 5.41599 Å , c = 17.2915 Å and β = 111.819°.[5] Photolysis in an argon matrix initially yields a short-lived nitrene. Further decomposition leads primarily to elemental nitrogen and sulfur dioxide.[6]
Uses
Sulfuryl diazide has been used as a reagent to perform reactions that remove nitrogen from heterocyclic compounds:[7][8][9]
- R1
–NH–R2
+ SO
2(N
3)
2 → R1
–R2
+ SO
2 + 2 N
2 + HN
3
See also
- Fluorosulfonyl azide
- Trifluoromethanesulfonyl azide
References
- ↑ 1.0 1.1 Curtius, Theodor; Schmidt, Friedrich (1922). "Action of sulfuryl azide, N3SO2N3, on p-xylene". Berichte der Deutschen Chemischen Gesellschaft B 55B: 1571–1581.
- ↑ Schmidt, Friedrich (1922). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft B 55B: 1581–1583. doi:10.1002/cber.19220550611.
- ↑ Schmidt, K. F. (1925). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft B 58B: 2409–2412. doi:10.1002/cber.19250581027.
- ↑ 4.0 4.1 4.2 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.
- ↑ Zeng, Xiaoqing; Beckers, Helmut; Bernhardt, Eduard; Willner, Helge (5 September 2011). "Synthesis and Characterization of Sulfuryl Diazide, O2S(N3)2". Inorganic Chemistry 50 (17): 8679–8684. doi:10.1021/ic201294b. ISSN 0020-1669. PMID 21815651. https://pubs.acs.org/doi/10.1021/ic201294b. Retrieved 22 September 2025.
- ↑ Dong, Xuelin; Deng, Guohai; Xu, Jian; Li, Hongmin; Zeng, Xiaoqing (1 November 2018). "Decomposition of Sulfonyl Azide Isocyanate and Sulfonyl Diazide: The Oxygen-Shifted Curtius Rearrangement via Sulfonyl Nitrenes". The Journal of Physical Chemistry A 122 (43): 8511–8519. doi:10.1021/acs.jpca.8b06655. ISSN 1089-5639. Bibcode: 2018JPCA..122.8511D. https://pubs.acs.org/doi/10.1021/acs.jpca.8b06655. Retrieved 22 September 2025.
- ↑ 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.
- ↑ Derek Lowe (July 7, 2021). "Carving Out Nitrogens: Pick Your Conditions". In The Pipeline. Science Translational Medicine. https://www.science.org/content/blog-post/carving-out-nitrogens-pick-your-conditions.
- ↑ 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. Bibcode: 2021ACIE...6020678Q.
Salts and covalent derivatives of the azide ion
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|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| HN3 | He | ||||||||||||||||||
| LiN3 | Be(N3)2 | B(N3)3 | CH3N3, C(N3)4 |
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)3 | Co(N3)2, Co(N3)3 |
Ni(N3)2 | CuN3, Cu(N3)2 |
Zn(N3)2 | Ga(N3)3 | Ge | As | Se(N3)4 | BrN3 | Kr | ||
| RbN3 | Sr(N3)2 | Y | Zr(N3)4 | Nb | Mo | Tc | Ru(N3)63− | Rh(N3)63− | Pd(N3)2 | AgN3 | Cd(N3)2 | In | Sn | Sb | Te | IN3 | Xe(N3)2 | ||
| CsN3 | Ba(N3)2 | 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 | Rf | Db | Sg | Bh | Hs | Mt | Ds | Rg | Cn | Nh | Fl | Mc | Lv | Ts | Og | |||
| ↓ | |||||||||||||||||||
| La | Ce(N3)3, Ce(N3)4 |
Pr | Nd | Pm | Sm | Eu | Gd(N3)3 | Tb | Dy | Ho | Er | Tm | Yb | Lu | |||||
| Ac | Th | Pa | UO2(N3)2 | Np | Pu | Am | Cm | Bk | Cf | Es | Fm | Md | No | Lr | |||||
 |  |
