dimethyliodonium | 24400-13-3

• 分子结构分类: 有机化合物
• 英文名称: dimethyliodonium
• 英文别名: dimethyl-iodonium cation；Dimethyliodonium-Kation；Dimethyliodoniumion；Dimethyljodonium；Dimethyliodanium
• CAS: 24400-13-3
• 化学式: C₂H₆I
• 分子量: 156.974
• InChiKey: HICOKSVOUCMYLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：

  2-二甲氨基乙基乙酸酯 、 dimethyliodonium 生成 乙酰胆碱 、 碘甲烷
  参考文献：
  名称：

  Ionic Hydrogen Bonds in Bioenergetics. 4. Interaction Energies of Acetylcholine with Aromatic and Polar Molecules

  摘要：

  The binding energies of the quaternary ions(CH3)(4)N+ and acetylcholine (ACh) to neutral molecules have been measured by pulsed high-pressure mass spectrometry and calculated ab initio, to model interactions in the acetylcholine receptor channel, Binding energies to C6H6 and C6H5CH3 are similar to those to H2O (33-42 kJ/mol (8-10 kcal/mol)), but are weaker than those to polar organic ligands such as CH3CO2CH3 (50-63 kJ/mol (12-15 kcal/mol)) and to amides (up to 84 kJ/mol (20 kcal/mol)). These data suggest that aromatic residues that line the groove leading to the ACh receptor site may provide stabilization comparable to water, and therefore allow entry from the aqueous environment, yet do not bind ACh as strongly as polar protein groups, and therefore allow transit, without trapping, to the receptor site. Four of the five distinct ACh conformers located computationally are stabilized by internal C-H ... O hydrogen bonds involving the quaternary ammonium group, which is supported by the thermochemistry of the protonated analogue, CH3CO2CH2CH2N(CH3)(2)H+, and by the measured bonding energy between models of the ACh end groups, (CH3)(4)N+ and CH3CO2CH3. Each conformer forms a number of stable complexes with water or benzene. Several possible roles for an ACh conformational change upon entry into the channel are discussed, including partial compensation for the loss of bulk solvation. An additional role for the aromatic environment is also suggested, namely lowering the energy barrier to the formation of the active all-trans ACh rotamer required at the receptor site.

  DOI：

  10.1021/ja982549s
• 作为产物：
  描述：

  丙酮 、 碘甲烷 生成 Dimethyl-methoxy-carboniumion 、 dimethyliodonium 、 1,2-dimethyl-1λ³-diiodan-2-ium-1-yl 、
  参考文献：
  名称：

  Jortay, C.; Flammang, R.; Maquestiau, A., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 10, p. 727 - 734

  摘要：

  DOI：