p-chlorophenyl dithio-2-furoate | 216453-14-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: p-chlorophenyl dithio-2-furoate
• 英文别名: (4-Chlorophenyl) furan-2-carbodithioate
• CAS: 216453-14-4
• 化学式: C₁₁H₇ClOS₂
• 分子量: 254.761
• InChiKey: FUKALCUCJLSXIW-UHFFFAOYSA-N

物化性质

• 沸点：
  367.2±48.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡啶 、 p-chlorophenyl dithio-2-furoate 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Kinetics and Mechanism of the Pyridinolysis of Aryl Furan-2-carbodithioates in Acetonitrile

  摘要：

  Kinetic studies on the pyridinolysis of aryl furan-2-carbodithioates 1 are carried out at 60.0 degreesC in acetonitrile. The biphasic rate dependence on the pyridine basicity with a breakpoint at pK(a)degrees = 5.2 is interpreted to indicate a change of the rate-limiting step from breakdown (betax = 0.7-0.8) to formation (betax = 0.2) of the tetrahedral intermediate, T+/-:, at the breakpoint as the basicity of the pyridine nucleophile is increased. Observation of the breakpoint is possible with pyridines since the expulsion rate of the pyridine (k-(a)) from T+/- is sufficiently low, with the low k(-a)/k(b) ratio leading to a low breakpoint, pK(a)degrees. The clear-cut change in the cross-interaction constants, pxz, from a positive (rhoxz = +0.86) to a small negative (rhoxz = -0.11) value at the breakpoint supports the mechanistic change proposed. The magnitudes of rhoz and activation parameters are also consistent with the proposed mechanism.

  DOI：

  10.1021/jo0264269
• 作为产物：
  描述：

  S-(4-氯苯基)呋喃-2-硫代甲酸酯 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 p-chlorophenyl dithio-2-furoate
  参考文献：
  名称：

  Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile

  摘要：

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v