dimethylchloronium | 24400-15-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: dimethylchloronium
• 英文别名: dimethyl-chloronium cation；Dimethylchloranium
• CAS: 24400-15-5
• 化学式: C₂H₆Cl
• 分子量: 65.5226
• InChiKey: DONGATCMJJKNOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  dimethylchloronium 在 氨 作用下， 生成 氯甲烷 、 methylammonium cation
  参考文献：
  名称：

  Chloronium ions as alkylating agents in the gas-phase ion-molecule reactions with negative temperature dependence

  摘要：

  DOI：

  10.1021/ja00365a005
• 作为产物：
  描述：

  氯甲烷 60.0 ℃ 、226.65 Pa 条件下， 生成 dimethylchloronium
  参考文献：
  名称：

  Stone, John A.; Lin, Margaret S.; Varah, Jeffrey, Canadian Journal of Chemistry, 1981, vol. 59, p. 2412 - 2416

  摘要：

  DOI：

文献信息

• Gas-phase heteroaromatic substitution. 3. Electrophilic methylation of furan and thiophene by CH₃XCH₃₊ (X = fluoro, chloro) ions
  作者：Giancarlo Angelini、Gaetano Lilla、Maurizio Speranza

  DOI：10.1021/ja00389a035

  日期：1982.12

  CH/sub 3/ClCH/sub 3//sup +/ confirms its inherent affinity toward n-type nucleophilic centers by attacking preferentially the heteroatom of 3 and 4. In light of the previous results concerning CH/sub 3/XCH/sub 3//sup +/ methylation of pyrroles, it is concluded that gas-phase attack of CH/sub 3/XCH/sub 3//sup +/ on simple five-membered heteroaromatics is essentially regulated by the electrostatic interaction

  先前对 CH/sub 3/XCH/sub 3//sup +/ (X = F 或 Cl) 离子对吡咯和 N-甲基吡咯的气相甲基化进行的辐解研究，来自 CH 的 ..gamma.. 辐解/sub 3/X，扩展为呋喃 (3) 和噻吩 (4)。讨论了通过分子内 1,2 甲基转移发生的取代和随后异构化的机制，并评估了所选亲电子物种的底物和位置选择性。至于吡咯，呋喃和噻吩的气相CH/sub 3/FCH/sub 3//sup +/甲基化的特点是缺乏底物区分（k/sub S//k/sub B/ = 1.2 (3) , 0.8 (4))，伴随着对具有最高负净电荷的底物位置的明显位置选择性（O:..cap alpha..:..beta.. = 36%:35%:29% for 3; S:..cap alpha..:..beta.. = 19%:43%:38% for 4)。相反，CH/sub 3/ClCH/sub
• Gas-phase protonation and methyl cation transfer from methyl halide ions
  作者：R. Houriet、E. Rolli、R. Flammang、A. Maquestiau、G. Bouchoux

  DOI：10.1002/oms.1210221203

  日期：1987.12

  AbstractThe ion‐molecule reactions between [CH3X]+˙ [CH3XH] +, [CH3XCH3]+ ions (X = F, Cl, Br, I) and a number of nucleophiles have been studied by ion cyclotron resonance techniques. Protonation of the nucleophiles is observed to occur from both the molecular ions [CH3]X+˙ and protonated species [CH3XH]+ whereas dimethylhalonium ions [CH3XCH3]+ react principally by methyl cation transfer. A notable exception occurs in methyl iodide where the molecular ions [CH3I]+˙ act both as proton and methyl cation donors, whereas dimethyliodonium ions are found unreactive. The results are discussed with reference to the use of alkyl halides as reagent gases in chemical ionization experiments.
• Site of gas-phase methylation of l-phenyl-2-aminopropane
  作者：Herman Zagppey、Roel H. Fokkens、Steen Ingemann、Nico M. M. Nibbering、Helena Florencio

  DOI：10.1002/oms.1210260610

  日期：1991.6

  AbstractThe regioselectivity of methyl cation transfer from (CH3)2F+, (CH3)2Cl+ and (CH3)3O+ to 1‐phenyl‐2‐aminopropane was studied by Fourier transform ion cyclotron resonance in combination with collision‐induced dissociation and neutralization‐reionization mass spectrometry of the stable [M + CH3]+ ions formed in a chemical ionization source. The (CH3)2F+ ion transfers a methyl cation to the NH2 group and the phenyl ring with almost equal probability. Predominant CH3+ transfer to the NH2 group is observed for the (CH3)2Cl+ ion whereas the (CH3)3O+ ion reacts almost exclusively at the amino group. The preference for methylation at NH2 is discussed in terms of a lower methyl cation affinity of the phenyl ring than of the amino group and the existence of an energy barrier for methylation of the phenyl moiety.
• Methyl cation affinities
  作者：Terrance B. McMahon、Thomas. Heinis、Gordon. Nicol、Jamey K. Hovey、Paul. Kebarle

  DOI：10.1021/ja00231a002

  日期：1988.11
• Attina, Marina; Cacace, Fulvio; Ricci, Andreina, Angewandte Chemie, 1991, vol. 103, # 11, p. 1527 - 1529
  作者：Attina, Marina、Cacace, Fulvio、Ricci, Andreina

  DOI：——

  日期：——