N,N,S,S'-Tetramethyl-dithiocarbamidium-jodid | 13196-72-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N,S,S'-Tetramethyl-dithiocarbamidium-jodid
• 英文别名: bis(methylsulfanyl)methylidene-dimethylazanium;iodide
• CAS: 13196-72-0
• 化学式: C₅H₁₂NS₂*I
• 分子量: 277.193
• InChiKey: QGZMRPGYKHXDKM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.29
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  氰化汞 、 N,N,S,S'-Tetramethyl-dithiocarbamidium-jodid 生成 2-Dimethylamino-2-methylsulfanyl-malononitrile
  参考文献：
  名称：

  S-烷基硫脒盐。二、S-烷基硫脒碘化物与汞化合物的反应

  摘要：

  已经研究了 S-烷硫基碘化物与一些汞化合物的反应。发现羧酸汞与碘化 S-烷基硫代脒反应，得到相应的酸酐和酰胺以及烷基硫基汞碘化物，产率良好。此外，确定氰化汞与碘化物的反应通过消除烷基巯基碘化汞得到α-二甲氨基丙二腈。此外，通过用氰化银处理碘化S-乙基硫代苯基乙酰吗啉，以87%的产率获得α-吗啉代-β-苯基丙烯腈。

  DOI：

  10.1246/bcsj.41.673
• 作为产物：
  描述：

  N,N-二甲基二硫代氨基甲酸 、 碘甲烷 生成 N,N,S,S'-Tetramethyl-dithiocarbamidium-jodid
  参考文献：
  名称：

  S-烷基硫脒盐。二、S-烷基硫脒碘化物与汞化合物的反应

  摘要：

  已经研究了 S-烷硫基碘化物与一些汞化合物的反应。发现羧酸汞与碘化 S-烷基硫代脒反应，得到相应的酸酐和酰胺以及烷基硫基汞碘化物，产率良好。此外，确定氰化汞与碘化物的反应通过消除烷基巯基碘化汞得到α-二甲氨基丙二腈。此外，通过用氰化银处理碘化S-乙基硫代苯基乙酰吗啉，以87%的产率获得α-吗啉代-β-苯基丙烯腈。

  DOI：

  10.1246/bcsj.41.673

文献信息

• Hindered rotation in dithiocarbamoyl compounds by NMR measurements
  作者：J.L. Richards、D.S. Tarbell、E.H. Hoffmeister

  DOI：10.1016/s0040-4020(01)96860-7

  日期：1968.1

  downfield shifts of 0·40 to 0·60 ppm for the protons on carbon attached to nitrogen or sulfur when compared to 2-methylimino-1,3-dithiolane. Hindered rotation was observed around the CN bond of methyl N,N-dialkyldithio-carbamates at ambient temperature (about 37°) by NMR, but none was observed in the corresponding thiuram disulfides at ambient temperature.

  N，N-二烷基二硫代氨基甲酸甲酯，四甲基秋兰姆二硫化物和双甲硫基-N-甲基甲亚胺的烷基化已显示出相同的对称二硫代氨基甲salt盐，其是由硫酮硫原子上的烷基化产生的。二硫代氨基甲酸铵离子的NMR光谱显示离子中的电荷分布大致相等，导致质子在附着于氮或硫的碳原子上的低场偏移为0·20至0·50 ppm。它的环状类似物2-二甲基氨基-1,3-二硫代亚硒酸根离子表明，其电荷几乎是均匀分布的，与2相比，附着在氮或硫上的碳上的质子的下场位移为0·40至0·60 ppm。 -甲基亚氨基-1，3-二硫杂环戊烷。通过NMR在环境温度（约37°）下观察到N，N-二烷基二硫代氨基甲酸甲酯的CN键周围的旋转受阻，
• 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.
• Hartke,K. et al., Chemische Berichte, 1966, vol. 99, p. 3268 - 3276
  作者：Hartke,K. et al.

  DOI：——

  日期：——
• Okecha,S.A.; Stansfield,F., Journal of the Chemical Society. Perkin transactions I, 1977, p. 1811 - 1814
  作者：Okecha,S.A.、Stansfield,F.

  DOI：——

  日期：——
• SCHLINGENSIEF K. H.; HARTKE K., ARCH. PHARM. <APBD-AJ>, 1978, 311, NO 5, 369-381
  作者：SCHLINGENSIEF K. H.、 HARTKE K.

  DOI：——

  日期：——