thiophosphoryl triazide | 4635-47-6

• 英文名称: thiophosphoryl triazide
• 英文别名: Triazido(sulfanylidene)-lambda5-phosphane；triazido(sulfanylidene)-λ5-phosphane
• CAS: 4635-47-6
• 化学式: N₉PS
• 分子量: 189.1
• InChiKey: FNEALECKGPQTSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  thiophosphoryl triazide 生成 2,4-diphospha-3,5-diaza-thiole
  参考文献：
  名称：

  SN2P2：中性五元硫-光气（III）环

  摘要：

  通过快速热解SP（N 3）3合成了新型芳香环化合物2,4-二磷-3-3,5-二氮杂硫醇（环-SNPNP），并通过红外光谱和15 N同位素标记进行了表征。量子化学计算表明，它是通过SNP从头到尾的二聚化以及随后从高度不稳定的船形六元环化合物环SNPSNP中消除硫原子而形成的。

  DOI：

  10.1002/anie.201409868
• 作为产物：
  描述：

  三氯硫磷 、 sodium azide 以 乙腈 为溶剂， 生成 thiophosphoryl triazide
  参考文献：
  名称：

  Synthesis and Characterization of the Phosphorus Triazides OP(N₃)₃ and SP(N₃)₃

  摘要：

  Two explosive triazides of phosphorus(V), OP(N-3)(3) and SP(N-3)(3), have been prepared as neat substances and structurally characterized. Both compounds can be handled in gas, liquid, and solid states in submillimolar quantities. The melting points of OP(N-3)(3) and SP(N-3)(3) are +22 and -30 degrees C, respectively. The two triazides have been characterized by IR (Ar matrix and gas phase) and Raman (solid) spectroscopies. Their single-crystal structures were obtained by X-ray diffraction and found to be significantly distorted from the predicted ideal C-3 symmetry because of intermolecular interactions. The spectroscopic and structural properties are discussed in combination with density functional theory calculations.

  DOI：

  10.1021/ic201802x
• 作为试剂：
  描述：

  N,N',N'-[tris(trimethyl)silyl]hydrazinediphenylphosphane 在 thiophosphoryl triazide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 3.0h， 以94%的产率得到
  参考文献：
  名称：

  On the Staudinger Reaction of SP(N ₃ ) ₃ with PPh ₃ and(Me ₃ Si) ₂ N–(Me ₃ Si)N–PPh ₂

  摘要：

  AbstractThe Staudinger reactions of SP(N3)3 (1) with 1, 2 and 3 equiv. of triphenylphosphane PPh3 and (TMS)2N–(TMS)N–PPh2 (2) have been investigated (TMS = Me3Si). Reaction with PPh3 yields the single and double Staudinger products SP(N3)2NPPh3 (3) and SP(N3)(NPPh3)2 (4), but not the triple, while the reaction with 2 results only in the formation of the single Staudinger product SP(N3)2NPPh2[N(TMS)N(TMS)]2 (5). Compound 5 is air‐ and moisture‐sensitive but stable under argon over a long period in the solid state and in common organic solvents. Although there are covalently bound azide groups in 3, 4 and 5, these Staudinger products are neither shock‐ nor heat‐sensitive in contrast to 1. Furthermore 3, 4 and 5 are easily prepared in bulk (yield > 95 %), and unlimitedly stable when cooled and stored in the dark. Compound 5 is thermally stable up to over 150 °C while 3 and 4 are stable only up to 96 °C. However, when a solution of 5 is heated, a new surprising eight‐membered ring (6) is formed in an intermolecular TMS–N3 elimination reaction. The structure and bonding is discussed on the basis of experimental X‐ray data and theoretical B3LYP calculations (thermodynamics, energy landscape and charge distribution). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejic.200501131

文献信息

• Experimental Observation of the 16-Electron Molecules SPN, SNP, and Cyclic PSN
  作者：Xiaoqing Zeng、Helmut Beckers、Helge Willner、Joseph S. Francisco

  DOI：10.1002/anie.201108636

  日期：2012.4.2

  triatomic ring: Novel thiazylidynephosphane (SNP) was produced by either flash vacuum pyrolysis (ca. 1000 °C) or laser photolysis (193 nm) of SP(N3)3. Its photointerconversion to cyclic thiazaphosphirine (cyc‐PSN) and thiophosphoryl nitride (SPN) was found in Ar matrix at 16 K. Cyc‐PSN is the first experimentally observed 16‐electron cyclic triatomic molecule.

  16-电子三原子环：通过SP（N 3）3的快速真空热解（约1000°C）或激光光解（193 nm）制得的新型硫代噻吩基膦（SNP）。其photointerconversion环状thiazaphoSPhirine（CYC -PSN）和硫代磷氮化物（SPN）的混合物在氩基质在16 K.发现的Cyc -PSN是第一实验观察到的16-电子环状三原子分子。
• Synthesis of Intermediary P3 Phosphazenium Framework and Its Derivatization to Chiral Cationic Macrocycles Including Two P3 Phosphazenium Units with Hydrogen Bond Donor Sites
  作者：Masahiro Terada、Kengo Goto、Takashi Ikehara、Azusa Kondoh

  DOI：10.3987/com-14-s(k)98

  日期：——

  A new synthetic route to key intermediary phosphonium possessing a P3 phosphazene framework was developed. The reaction of the obtained intermediary phosphonium with chiral diamine, (1 S,25)-1,2-diphenyl-1,2-ethanediamine, resulted in the formation of 18-membered macrocyclic bisphosphazenium, the structure of which was verified by single-crystal X-ray diffraction analysis. The macrocyclic bisphosphazenium showed potential application as a chiral anion receptor and a chiral template in asymmetric catalysis.