(4-(methylthio)benzyl)triethylphosphonium bromide | 154797-23-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4-(methylthio)benzyl)triethylphosphonium bromide
• CAS: 154797-23-6
• 化学式: Br*C₁₄H₂₄PS
• 分子量: 335.288
• InChiKey: MWGDDJBNCOMBDY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,1'-二茂铁二甲醛 、 (4-(methylthio)benzyl)triethylphosphonium bromide 在 n-BuLi 作用下， 以 further solvent(s) 为溶剂， 以46%的产率得到1,1'-bis[2-(4-(methylthio)phenyl)-(E)-ethenyl]ferrocene
  参考文献：
  名称：

  1,1'-Disubstituted Ferrocenes as Donors for Charge-Transfer Complexes. Synthesis, Structure, Conductivity, and Magnetic Properties

  摘要：

  Starting from ferrocene-1,1'-dicarbaldehyde (1), the novel electron donors 1,1'-bis[(5,6-dihydro-1,3-dithiolo[4,5b][1,4]dithiin-2-ylidene)methyl]ferrocene (5), 1,1'-bis[(1,3-benzodithiol-2-ylidene)methyl]ferrocene (6), and 1,1'-bis[2-[4-)methylthio)phenyl]-(E)-ethenyl]ferrocene (7) were prepared, and their electrochemical properties were studied. 5 and 6 undergo two reversible oxidation processes, whereas for 7 only the first electron removal is reversible in character. Crystals of 5 are monoclinic, space group P2(1)/c, with a = 12.448(1) angstrom, b = 12.178(1) angstrom, c = 16.219(1) angstrom, beta = 104.5(1)degrees, and Z = 4. In the solid state, molecules of 5 assume an eclipsed conformation, with the two substituents lying on top of each other (intramolecular stacking). 5 and 6 easily form 1:2 electron-transfer complexes with TCNQ (8 and 9, respectively), whereas 7 leads to a charge-transfer (CT) complex (10). Polycrystalline samples of 8 and 9 are conducting: sigma(rt)(8) = 0.26 S.cm-1 and sigma(rt)(9) = 0.20 S.cm-1. SQUID magnetic susceptibility measurements of 8 and 9 show these materials to undergo a phase transition dominated by a weak antiferromagnetic coupling (Curie-Weiss constants theta (8) = -3 K and theta (9) = -3 K). 10 is an insulator and is characterized by a very weak degree of electron transfer. Crystals of 10 are triclinic, space group P1BAR, with a = 7.796(1) angstrom, b = 8.607(1) angstrom, c = 16.396(2) angstrom, alpha = 92.88(1)degrees, beta = 97.83(1)degrees, gamma = 100.95(1)degrees, and Z = 1. In the CT complex 10, the donor 7 assumes an antiperiplanar conformation, thus leading to a 1D-DADA type structure.

  DOI：

  10.1021/om00016a027