methyl iodide salt of N,N'-dimethylimidazolidine-2-thione | 31774-54-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl iodide salt of N,N'-dimethylimidazolidine-2-thione
• 英文别名: 1,3-dimethyl-2-methylsulfanyl-4,5-dihydro-3H-imidazolium; iodide；1,3-Dimethyl-2-methylsulfanyl-4,5-dihydroimidazol-1-ium;iodide
• CAS: 31774-54-6
• 化学式: C₆H₁₃N₂S*I
• 分子量: 272.153
• InChiKey: CDNWTZRLRAYOEJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl iodide salt of N,N'-dimethylimidazolidine-2-thione 200.0 ℃ 、133.32 Pa 条件下， 生成 1,3-二甲基咪唑烷-2-硫酮
  参考文献：
  名称：

  Macroheterocycles; XIX. A Convenient Synthesis ofN-Alkylated Thioureas

  摘要：

  DOI：

  10.1055/s-1984-30753
• 作为产物：
  描述：

  亚乙基硫脲 、 碘甲烷 在 18-冠醚-6 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 methyl iodide salt of N,N'-dimethylimidazolidine-2-thione
  参考文献：
  名称：

  Macroheterocycles; XIX. A Convenient Synthesis ofN-Alkylated Thioureas

  摘要：

  DOI：

  10.1055/s-1984-30753

文献信息

• Reaction of NN′-dimethylimidazolidine-2-thione with methyl iodide. Kinetic and thermodynamic aspects
  作者：Yasuhiko Kondo、Tetsuya Yamada、Shigekazu Kusabayashi

  DOI：10.1039/p29810000414

  日期：——

  The reaction of NN′-dimethylimidazolidine-2-thione with methyl iodide followed simple second-order kinetics in polar solvents, whereas in less polar solvents the reverse process made a significant contribution to the overall rate. The solvent effects on the forward rate constant were linearly correlated with those on the rate of the reaction of tetramethylthiourea with methyl iodide. However, the reactions

  的反应NN '-dimethylimidazolidine -2-硫酮与甲基碘，随后在极性溶剂中简单的二阶动力学，而在极性较小的溶剂中的逆过程制成的整体速率的显著贡献。溶剂对正向速率常数的影响与四甲基硫脲与甲基碘的反应速率线性相关。但是，两种1,2,4-三唑-3-硫酮衍生物与甲基碘的反应未显示任何此类相关性。从体积变化和测得的焓变，三个过渡态指数，（Δ 2 V ‡/Δ 2 °），Ñ Ť α在乙腈中确定，并且，约 分别为0.28、0.35和0.43。
• Specific Molecular Orbital Contributions to Nucleophilicity. The Thiocarbonyl Group as Priviledged Monitor to Pinpoint Active and Less Active Molecular Orbitals in Reactions with Methylating Agents
  作者：M. Arbelot、A. Allouche、K. F. Purcell、M. Chanon

  DOI：10.1021/jo00113a010

  日期：1995.4

  The rate constants for 41 compounds bearing a C=S function reacting with MeX (X = I, Tos) span 7 orders of magnitude. The PES spectra of these compounds display two very low energy peaks, which stand clearly apart from the other peaks. These two peaks correspond to the pi orbitals of the C-S group; one is its CS pi bonding orbital oriented out of the molecular plane (pi(CS)) and the other its p-type in-plane lone pair orbital (pi(S)). For some of the compounds, the HOMO is the pi(CS) orbital and for others the HOMO is the ns lone pair orbital. The best correlation (R = 0.96) between rate constants h and PES data is obtained when In(k) is plotted against the inverse of PES energy of the pi(S) lone pair orbital. Whether this lone pair orbital is the HOMO or the next lower HOMO has no importance. A modest correlation (R = 0.78) is obtained when In(k) is plotted against the inverse of PES energy of the pi(CS) bonding orbital, An attempt to correlate the calculated energy of the third highest occupied orbital (from AM1 calculations) with In(h) provides a complete scattering of data (R < 0.1), but the calculated energy of the second lone pair orbital sigma(S) (approximate to 90 kcal mol-l deeper than the HOMO) correlates reasonably with In(h) (R = 0.88). The energies of the S 2s and 2p core orbitals (calculated for 13 cyclic compounds with the HF/3-21G technique to be 4000 to 5500 kcal mol(-1) deeper than HOMO) correlate with In(k) (R = 0.86) as well as does that of the second lone pair orbital os. These results are the first where both frontier orbitals and core orbitals display correlation with overall reactivity. They are discussed in terms of direct (perturbational) versus indirect (nonperturbational) concepts.
• ASSEF G.; KISTER J.; METZGER J., BULL. SOC. CHIM. FRANCE, 1979, PART. 2, NO 3-4, 165-176
  作者：ASSEF G.、 KISTER J.、 METZGER J.

  DOI：——

  日期：——
• KISTER J.; ASSEF G.; DOU H. J.-M.; METZGER J., TETRAHEDRON <TETR-AB>, 1976, 32, NO 12 1395-1398
  作者：KISTER J.、 ASSEF G.、 DOU H. J.-M.、 METZGER J.

  DOI：——

  日期：——
• Kondo, Yasuhiko; Inoue, Motoo; Kusabayashi, Shigekazu, journal of the chemical society-perkin transactions 2, 1983, p. 1217 - 1222
  作者：Kondo, Yasuhiko、Inoue, Motoo、Kusabayashi, Shigekazu

  DOI：——

  日期：——