CCl3 | 14478-07-0

• 分子结构分类: 无机化合物 - 均质非金属化合物 - 其他非金属卤化物
• 英文名称: CCl3
• 英文别名: trichloromethyl(1-)；trichloromethanide；Methane, trichloro-, ion(1-)；trichloromethane
• CAS: 14478-07-0
• 化学式: CCl₃
• 分子量: 118.37
• InChiKey: PMBRBOODEWULOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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

• 作为反应物：
  描述：

  CCl3 、 1-金刚烷甲醛 生成 1-Adamantan-1-yl-2,2,2-trichloro-ethanol
  参考文献：
  名称：

  X-ray diffraction studies of crystalline trihalomethyl ketones (RCOCX3) reveal an unusual structural deformation about the carbonyl group

  摘要：

  X-ray crystallographic studies of a set of trihalomethyl ketones (4, 5, and 6) indicate that the carbonyl oxygen is displaced significantly toward the trihalomethyl group, probably as a consequence of oxygen lone pair delocalization into the sigma* orbital of CO-CX3.

  DOI：

  10.1016/s0040-4039(00)60847-x
• 作为产物：
  描述：

  [3H]氯仿 在 四甲基氢氧化铵 、 2,4-滴二甲胺盐 作用下， 以 水 为溶剂， 生成 CCl3
  参考文献：
  名称：

  尿素和酰胺在高度碱性介质中作为偶极非质子传递溶剂。动力学碱性对溶剂组成的依赖性

  摘要：

  偶极非质子溶剂-水-HO的碱度-与酰胺和脲作为有机成分的系统已被研究了动力学因为以前的信息不可用，不包括一些ħ -用于含水二甲基甲酰胺（DMF）和四甲基脲（TMU）测定的值。发现碱度随有机组分的摩尔分数的增加至少与在二甲基亚砜水溶液（DMSO）中相同。例如，在氯仿的氚吨情节日志的斜率（ķ 2 /摩尔-1分米3小号-1）相对于X当TMU和环状脲，1,3-二甲基咪唑烷基-2-酮（DMI）和1,3-二甲基-3,4,5,6-时，尿素（尿素）在11.4–14.6之间（相比，在DMSO水溶液中为11.0）。使用四氢嘧啶-2（1 H）-one（DMPU）作为溶剂混合物中的有机组分。在TMU水溶液中，使用线性自由能相关性从动力学结果推断出酸度函数H –。与文学价值的一致是显而易见的。该方法还用于推断DMPU水溶液中的H –值。在目前的工作基础上，可推荐将尿素水用作高碱性介质中的溶剂。酰胺，二甲基甲酰胺和二

  DOI：

  10.1039/a808435a

文献信息

• Reactivity of the radical anion OCC-
  作者：Jane M. Van Doren、Thomas M. Miller、Amy E. Stevens Miller、A. A. Viggiano、Robert A. Morris、John F. Paulson

  DOI：10.1021/ja00069a045

  日期：1993.8

  consistent with the relatively small C(-)-CO bond energy and the proposed electronic structure of the ground state anions in which both radical and charge are centered on the terminal carbon. Similarities are noted between the chemistry of OCC(-) and its neutral analogue OCC and between the chemistry of OCC(-) and the radical anions O(-) and 0-Csub6Hsub4(-). Most reaction products observed are consistent

  摘要 : 通过测定 29 个离子-分子反应中每一个的速率系数、产物和支化分数，研究了自由基阴离子 OCC(-) 在 298 K 的气相中的特征反应性。观察到各种各样的反应，包括 H、H(+) 和 Hsub2(+) 的抽象、亲核置换、电荷转移和涉及电子脱离的反应。许多反应涉及 C(-)-CO 键的裂解，这与相对较小的 C(-)-CO 键能和基态阴离子的拟议电子结构一致，其中自由基和电荷都集中在末端碳。注意到 OCC(-) 化学与其中性类似物 OCC 之间以及 OCC(-) 化学与自由基阴离子 O(-) 和 0-Csub6Hsub4(-) 之间的相似性。观察到的大多数反应产物与涉及 OCC(-) 中的末端碳对中性反应伙伴的初始攻击的反应机制一致。HCCO 的气相酸度介于 CHsub3NOsub2 和 CHsub3CHO 之间，产生 1502 + 或 - 8 > delta G 脱酸（HCCO）>
• Gas-Phase Carbene Radical Anions: New Mechanistic Insights
  作者：Stephanie M. Villano、Nicole Eyet、W. Carl Lineberger、Veronica M. Bierbaum

  DOI：10.1021/ja801819b

  日期：2008.6.1

  The gas-phase reactivity of the CHCl*- anion has been investigated with a series of halomethanes (CCl4, CHCl3, CH2Cl2, and CH3Cl) using a FA-SIFT instrument. Results show that this anion primarily reacts via substitution and by proton transfer. In addition, the reactions of CHCl*- with CHCl3 and CH2Cl2 form minor amounts of Cl2*- and Cl-. The isotopic distribution of these two products is consistent

  已使用 FA-SIFT 仪器研究了 CHCl*- 阴离子与一系列卤代甲烷（CCl4、CHCl3、CH2Cl2 和 CH3Cl）的气相反应性。结果表明，该阴离子主要通过取代和质子转移进行反应。此外，CHCl*- 与 和 的反应会形成少量的 Cl2*- 和 Cl-。这两种产物的同位素分布与插入消除机制一致，其中阴离子插入 C-Cl 键形成不稳定的中间体，从而消除 Cl2*- 或 Cl- 和 Cl*。已知中性和阳离子卡宾插入单键；然而，这是对卡宾阴离子的这种反应性的首次观察。
• Aksnes, Gunnar; Gierstae, Roald; Wulvik, Erik A., Phosphorus and Sulfur and the Related Elements, 1988, vol. 39, p. 141 - 152
  作者：Aksnes, Gunnar、Gierstae, Roald、Wulvik, Erik A.

  DOI：——

  日期：——
• Competing electron transfer, proton abstraction and nucleophilic substitutions in gas-phase reactions of (radical) anions with chloro- and bromomethanes
  作者：P. O. Staneke、G. Groothuis、S. Ingemann、N. M. M. Nibbering

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

  日期：1996.7

  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.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: C: MVol.D2, 4.1.2.7.4.3, page 225 - 227
  作者：

  DOI：——

  日期：——