9,12-dimercapto-1,2-carborane | 75572-47-3

• 英文名称: 9,12-dimercapto-1,2-carborane
• 英文别名: 9,12-dimercapto-1,2-dicarba-closo-dodecaborane；9,12-dimercapto-1,2-closo-carborane；9,12-bis(mercapto)-o-carboane；9,12-dithiol-1,2-o-carborane；closo-9,12-(SH)2-1,2-C2B10H10
• CAS: 75572-47-3
• 化学式: C₂H₁₂B₁₀S₂
• 分子量: 208.359
• InChiKey: SRRPEGCTXIWJBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  9,12-dimercapto-1,2-carborane 在 碘甲烷 作用下， 以 乙醇 为溶剂， 以89%的产率得到9,12-bis(methylthio)-o-carborane
  参考文献：
  名称：

  Zakharkin, L. I.; Pisareva, I. V., Phosphorus and Sulfur and the Related Elements, 1984, vol. 20, p. 357 - 370

  摘要：

  DOI：
• 作为产物：
  描述：

  9,12–bis(triisopropylsilylmercapto)–1,2–dicarba–closo–dodecaborane 在 盐酸 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 24.0h， 以90%的产率得到9,12-dimercapto-1,2-carborane
  参考文献：
  名称：

  B‐Mercaptocarboranes: A New Synthetic Route

  摘要：

  AbstractA novel route for synthesis of B‐mercaptocarboranes is described. The reaction proceeds through Pd‐catalyzed iodine exchange with the sulfur nucleophile TIPS–SH in mono‐ and diiodinated ortho‐, meta‐, and para‐carboranes. Self‐assembled monolayers of selected B‐mercaptocarboranes on a gold surface were analyzed by X‐ray photoelectron spectroscopy and their water contact angles were assessed.

  DOI：

  10.1002/ejic.201201518

文献信息

• B–H···π Interaction: A New Type of Nonclassical Hydrogen Bonding
  作者：Xiaolei Zhang、Huimin Dai、Hong Yan、Wenli Zou、Dieter Cremer

  DOI：10.1021/jacs.6b01249

  日期：2016.4.6

  interaction between the carborane BH bonds and the phosphine aryl substituents involves a BH···π H-bond (H···π distance: 2.40-2.76 Å). (1)H NMR experiments reveal that B-H···π interactions exist in solution according to measured (1)H(11)B} signals at ambient temperatures in the range 0.0 ≤ δ ≤ 0.3 ppm. These are high-field shifted by more than 1.5 ppm relative to the (1)H(11)B} signals obtained for

  首次利用量子化学预测和实验实现描述了涉及 BH…π 相互作用的非经典氢 (H) 键合。在气相中，B2H6…苯 (ΔE = -5.07 kcal/mol) 或碳硼烷…苯 (ΔE = -3.94 kcal/mol) 络合物在还原态下观察到 BH…π 氢键温度。Ir-二巯基-碳硼烷复合物 [Cp*Ir(S2C2B10H10)] 旨在与膦 PR3（R = C6H4X，X = H，F，OMe）反应生成 [Cp*Ir(PR3)S2C2B10H10]，用于研究 BH ···环境温度下的π相互作用。X 射线衍射研究表明，碳硼烷 BH 键和膦芳基取代基之间的相互作用涉及 BH...π H 键（H...π 距离：2.40-2.76 Å）。(1)H NMR 实验表明，根据在环境温度 0.0 ≤ δ ≤ 0.3 ppm 范围内测得的 (1)H(11)B} 信号，溶液中存在 BH…π 相互作用。这些是相对于没有 BH…π
• Symmetry Breaking of Atomically Precise Fullerene-like Metal Nanoclusters
  作者：Jia-Hong Huang、Yubing Si、Xi-Yan Dong、Zhao-Yang Wang、Li-Ying Liu、Shuang-Quan Zang、Thomas C. W. Mak

  DOI：10.1021/jacs.1c05568

  日期：2021.8.18

  dodecahedral shell first induced symmetry breaking to generate chiral Ag13@Ag20-nCun (6 ≥ n ≥ 2) containing two acetonitrile ligands in space group P212121, and then produced symmetric all-thiolated Ag13@Ag20-nCun (20 ≥ n ≥ 13) in the higher space group Im3̅. The selectively copper-doped Ag13@Ag20-nCun (6 ≥ n ≥ 2) cluster has its structure reorganized to a lower symmetry that shows chiroptical activity

  此处我们报告一个中性类富勒烯芯-壳homosilver银13 @Ag 20纳米簇由非手性的二齿硫醇配体（9,12-二巯基-1,2-完全保护的闭合碳-carborane，C 2乙10 ħ 10小号2 H 2 )，在中心对称空间群R 3̅ 中结晶。在十二面体壳中连续掺杂 Cu 首先引起对称性破缺以生成手性 Ag 13 @Ag 20- n Cu n (6 ≥ n ≥ 2)，在空间群P 2 1 2 中含有两个乙腈配体1 2 1，然后在较高空间群Im 3̅中产生对称的全硫醇化Ag 13 @Ag 20- n Cu n (20 ≥ n ≥ 13) 。选择性掺杂铜的 Ag 13 @Ag 20- n Cu n (6 ≥ n ≥ 2) 簇的结构重组为较低的对称性，显示出手性光学活性。此外，Ag 13 @Ag 20- n Cu n (6 ≥ n ≥ 2) 的结构畸变在手性R -/ S 中进一步扩大-环氧丙烷，其诱导了更显着的基于核的
• Boron-Substituted <i>o</i>-Carboranetrithiol To Construct Trimeric Cobalt Clusters
  作者：Xiaolei Zhang、Xiao Tang、Jiajia Yang、Yizhi Li、Hong Yan、Vladimir I. Bregadze

  DOI：10.1021/om400097m

  日期：2013.3.25

  A new o-carborane-based boron-substituted trithiol has been prepared via direct attachment of sulfur atoms to the B8/B9/B12 vertexes of o-carborane. On the basis of the trithiolate ligand, both the neutral 51 cluster valence electron (CVE) and the cationic 50-CVE trimeric cobalt clusters have been synthesized and structurally characterized. Electrochemical observations demonstrate that the 51-CVE cluster is electron-overloaded and readily undergoes one-electron oxidation to yield the thermodynamically stable 50-CVE species.
• Synthesis of Boron-Fused 1,4-Dithiin via Cobalt-Mediated Disulfuration of Alkyne at the <i>o</i>-Carborane-9,12-dithiolate Unit
  作者：Xiaolei Zhang、Xiaodong Zou、Hong Yan

  DOI：10.1021/om500411b

  日期：2014.5.27

  : We present the first synthesis and characterization of a series of boron-fused 1,4-dithiin compounds through the reactions of newly established boron-substituted 16e half-sandwich complex Cp*Co(9,12-S2C2B10H10) with alkynes. The generated C2S2B2 ring in these 1,4-dithiin species is a stable structural motif with electron-negative sulfur atoms, as evidenced by theoretical calculation and its solid-state self-assembly. Single-crystal X-ray analysis indicates that C-carb-H center dot center dot center dot S hydrogen bonding is involved in the self-assemblies of these compounds, which serves as a compatible interaction with stronger C-carb-H center dot center dot center dot pi, C-carb-H center dot center dot center dot O, or C-carb-H center dot center dot center dot F hydrogen bonding. All new compounds are characterized by NMR, mass spectroscopy, and X-ray structural analysis.