Tribrommethylanion | 81193-44-4

• 分子结构分类: 无机化合物 - 混合金属/非金属化合物 - 过渡金属盐
• 英文名称: Tribrommethylanion
• 英文别名: tribromomethyl(1-)；tribromomethanide；tribromomethane
• CAS: 81193-44-4
• 化学式: CBr₃
• 分子量: 251.723
• InChiKey: NAOFFWRPLAJAEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  四溴化碳 在 hydroxide 作用下， 以 gas 为溶剂， 生成 Tribrommethylanion
  参考文献：
  名称：

  Competing electron transfer, proton abstraction and nucleophilic substitutions in gas-phase reactions of (radical) anions with chloro- and bromomethanes

  摘要：

  The product ion distributions and rates of the gas-phase reactions of two series of (radical) anions with chloro- and bromomethanes (CH3Cl, CH2Cl2, CHCl3, CCl4, CH3Br, CH2Br2, CHBr3 and CBr4) were determined with the use of Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry. The first series consists of anions (HO-, CH3O-, C2H5O-, C3H7O- and CH3S-), for which the corresponding neutral radicals have a relatively high electron affinity (EA > 150 kJ mol(-1)). The second series consists of (radical) anions (CH2S-., CH2 = CHCH2-, CH2 = C(CH3)CH2-, C6H4-. and C6H5-), for which the corresponding neutral species have a relatively low electron affinity (EA less than or equal to 100 kJ mol(-1)). These (radical) anions react mainly with the halomethanes to afford (i) halide ions, (ii) halomethyl anions with the same number of halogen atoms as in the parent halomethane and (iii) halomethyl anions with one halogen atom less than the parent substrate. The last process involves nucleophilic attack on a halogen atom and is particularly important in the reactions with substrates containing three or four halogen atoms. The halide ions may arise by a number of different pathways, such as S(N)2 substitution, alpha-elimination, halogen attack followed by dissociation of the thus formed halomethyl anion and overall dissociative electron transfer. The S(N)2 process is held responsible for the formation of halide ions in the reactions with monohalomethanes, whereas alpha-elimination is likely to be of importance only for the reactions with trichloro- and tribromomethanes. Attack on a halogen atom followed by dissociation of the ion generated initially is likely to be important if CCl4 or CBr4 is the substrate. Electron transfer is only a dominant pathway in the reactions of the CH2S-. ion with the halomethanes. The occurrence of electron transfer in the reactions of this ion with CHCl3, CCl4 and CHBr3 is evidenced by the formation of minor amounts of stable halomethane radical anions in addition to the generation of CH2SCl- or CH2SBr- ions and abundant halide ions. The interplay between the various possible reactions is discussed on the basis of thermodynamic considerations and the rates of the overall processes.

  DOI：

  10.1002/(sici)1099-1395(199607)9:7<471::aid-poc807>3.0.co;2-i

文献信息

• Bell, R. P.; Ford-Smith, M. H., Journal of the Chemical Society
  作者：Bell, R. P.、Ford-Smith, M. H.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: C: MVol.D2, 3.3, page 71 - 71
  作者：

  DOI：——

  日期：——
• Ionization and dissociation by electron impact in carbon tetrabromide
  作者：R Thorburn

  DOI：10.1088/0508-3443/16/9/422

  日期：1965.9