sodium N,N-dimethylmercaptoacetamide | 156098-01-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: sodium N,N-dimethylmercaptoacetamide
• 英文别名: Sodium;2-(dimethylamino)-2-oxoethanethiolate
• CAS: 156098-01-0
• 化学式: C₄H₈NOS*Na
• 分子量: 141.169
• InChiKey: AXKGQKTXVZISLI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.37
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  21.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (hydridotris(3,5-dimethyl-1-pyrazolyl)borate)nitrosylmolybdenum diiodide 、 sodium N,N-dimethylmercaptoacetamide 在 CH₂Cl₂ 作用下， 以 四氢呋喃 为溶剂， 以32.7%的产率得到bis(SCH₂CON(CH₃)2)(nitrosyl)[tris(3,5-dimethylpyrazolyl)borato]molybdenum 0.3CH₂Cl₂
  参考文献：
  名称：

  Hydrogen-Bonding and Polar Group Effects on Redox Potentials in Mo[HB(Me2pz)3](NO)(SR)2

  摘要：

  A series of Mo thiolate complexes with the formula Mo[HB(Me(2)pz)(3)] (NO)(SR)(2), R = Et (1), Bu(n) (2), CH2CONHCH3 (3), CH2CON(CH3)(2) (4), C2H4CONHCH3 (5), and C2H4CON(CH3)(2) (6), have been studied using the methods of cyclic voltammetry, IR and resonance Raman spectroscopy, and for 3 and 5, X-ray crystallography. The polar groups of the thiolate ligands exert an influence on the redox potentials reflected in the E(1/2) series for the Mo2+/Mo3+ redox couple recorded in CH3CN: 2, -0.960; 1, -0.940; 5, -0.820; 6, -0.750; 4, -0.740; 3, -0.643 V (relative to SCE). The corresponding frequencies for the nu(NO) band increase in the same order: 2, 1658; 1, 1661; 5, 1663; 6, 1664; 4, 1669; 3, 1671 cm(-1), showing a correlation between the redox potential and the nitrosyl frequency. Complex 3 belongs to space group P (1) over bar with a = 10.564(4) Angstrom, b = 12.160(5) Angstrom, c = 12.478(6) Angstrom, alpha = 110.27(3)degrees, beta = 92.64(4)degrees, gamma = 105.96(3)degrees, V = 1427.8(10) Angstrom(3), and Z = 2. Complex 5 belongs to space group P (1) over bar with a = 9.565(8) Angstrom, b = 11.480(9) Angstrom, c = 18.510(20) Angstrom, alpha = 73.35(8)degrees, beta = 77.38(8)degrees, gamma = 88.17(7)degrees, nu = 1899.2(31) Angstrom(3), and Z = 2. Complex 3 exhibits a single intraligand N-H...S hydrogen bond in the solid state, with even more extensive N-H...S bonding evident in solution. By contrast 5 forms an interligand N-H...O hydrogen bond which precludes the formation of N-H...S hydrogen bonds, Within the series of thiolate complexes examined, simple charge-dipole interactions appear to induce redox potential shifts of several hundred millivolts. The largest shift is observed in 3, which forms intraligand hydrogen bonds. These results underscore the likely importance of charge-dipole interactions involving ligated thiolate sulfur in iron-sulfur redox proteins. From this perspective, hydrogen bonding and its effects on redox potential should be viewed in terms of electrostatic influence exerted on the electronic structure of the redox center.

  DOI：

  10.1021/ja00094a036

文献信息

• Synthesis of dinitrosyl iron complexes (DNICs) with intramolecular hydrogen bonding
  作者：Show-Jen Chiou、Chien-Chu Wang、Chih-Ming Chang

  DOI：10.1016/j.jorganchem.2008.08.034

  日期：2008.11

  HSCH2CONHCH3 and HSCH2CON(CH3)2 containing a peptide bond are prepared for the synthesis of DNICs with/without intra-molecular hydrogen bonding, respectively. The IR ν(NO) bands of [(NO)2Fe(SCH2CONHCH3)2]− (2) appears at 1751, 1700 cm−1. In complex 2, the presence of intramolecular [NH⋯S] hydrogen bonding was verified by the observation of IR spectroscopy with N−H stretching frequency 3334 cm−1 (CDCl3)

  制备具有肽键的HSCH 2 CONHCH 3和HSCH 2 CON（CH 3）2分别用于合成具有/不具有分子内氢键的DNIC。红外ν [（NO）的（NO）带2的Fe（SCH 2 CONHCH 3）2 ] - （2）出现在1751，1700厘米-1。在配合物2中，通过NH拉伸频率为3334 cm -1（CDCl 3）的红外光谱观察，证实了分子内[NH⋯S]氢键的存在。），然后通过单晶X射线衍射确认，表明Ns距离为2.94Å。复杂2与显示菱形EPR光谱克1  = 2.039，克2  = 2.031和克3  = 2.013在冷冻ħ 2 O.配合物2和3，当暴露于光快速释放NO。在极性较小的溶剂中，光解反应所需的时间2是3的两倍。THF中2和3的光致化性的代表性时间过程显示NO-off能力：2  >  3。
• Bose, K.; Huang, J.; Haggerty, B. S., Inorganic Chemistry, 1997, vol. 36, p. 4596 - 4599
  作者：Bose, K.、Huang, J.、Haggerty, B. S.、Rheingold, A. L.、Salm, R. J.、Walters, M. A.

  DOI：——

  日期：——