Sulfuryl diazide
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IUPAC name Sulfuryl diazide | |
Other names Sulfuryl azide; Sulfonyl diazide | |
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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 |
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
- ^ a b Curtius, Theodor; Schmidt, Friedrich (1922). "Action of sulfuryl azide, N3SO2N3, on p-xylene". Berichte der Deutschen Chemischen Gesellschaft B. 55B: 1571–1581.
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: CS1 maint: multiple names: authors list (link) - ^ 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.
- ^ 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.
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: CS1 maint: multiple names: authors list (link) - ^ 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.
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: CS1 maint: multiple names: authors list (link) - ^ 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.
- ^ 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.
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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 |