S-亚硝基巯基乙醇 | 67616-44-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: S-亚硝基巯基乙醇
• 英文名称: 2-hydroxy-S-nitrosoethanethiol
• 英文别名: S-nitrosomercaptoethanol；2-nitrososulfanylethanol
• CAS: 67616-44-8
• 化学式: C₂H₅NO₂S
• 分子量: 107.133
• InChiKey: AVGNNQMFRRYDBY-UHFFFAOYSA-N

物化性质

• 沸点：
  215.6±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-亚硝基巯基乙醇 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-羟乙基二硫化物
  参考文献：
  名称：

  A Convenient Method for Production of Thionitrites and Disulfides Under Mild and Heterogeneous Condition

  摘要：

  Thiols can be readily converted to their corresponding thionitrite with a combination of inorganic acidic salts and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.

  DOI：

  10.1080/00397910008087194
• 作为产物：
  描述：

  2-巯基乙醇 在 氧化亚氮 作用下， 生成 S-亚硝基巯基乙醇
  参考文献：
  名称：

  Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity

  摘要：

  The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (alpha(1g) approximate to -1.30), but virtually independent of the basicity of the thiol (beta(nuc) approximate to 0-10)This dependence is ascribed to the presence of a nucleophile desolvation equilibrium (beta(d)) that is followed by the attack of the thiolate ion on the nitroso group (beta'(nuc)) via a concerted mechanism. The equilibrium constants for the loss of a nitroso group from a nitrosothiol and an N-nitrososulfonarni de were used to obtain the equilibrium constants for the different reactions involved. By using rate-equilibrium correlations, the parameters alpha(norm)(1g) ,beta(d), and beta('norm)(nuc) were obtained. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.060

文献信息

• Evaluation of transnitrosating ability of N-nitrosoguanidines to alkyl thiols and thiol amino acids
  作者：Lara Ribeiro、Luis García-Río、M. Eduarda Araújo

  DOI：10.1016/j.tet.2016.01.008

  日期：2016.3

  nitrosoguanidines react through the corresponding neutral form, and the nucleophiles in the thiolate anion form to give the corresponding S-nitrosothiol. Regarding cysteine, the existence of three macroscopic acidity constants influenced the kinetic behavior of the transnitrosation reaction. Transnitrosation rates (ktr) of the two possible nucleophilic species were obtained and it was found that NOBMG has lower

  在1中研究了亚硝基从1-亚硝基1-甲基3-甲苯磺酰胍（NOTSG）和1-亚硝基1-甲基3-苯甲酰胍（NOBMG）转移到某些硫醇（包括氨基酸半胱氨酸）。 pH范围在7到12之间。 测得的反硝化的表观双分子速率常数（k tr app）显示出钟形的pH依赖性，清楚地表明两个亚硝基胍都通过相应的中性形式反应，并且以硫醇盐阴离子形式的亲核试剂产生相应的S-亚硝基硫醇。关于半胱氨酸，三个宏观酸度常数的存在影响了反硝化反应的动力学行为。亚硝化率（k tr）获得了两种可能的亲核物质，发现由于苯甲酰基的吸电子效应较低以及由于分子内氢的建立可能使阴离子结构稳定，因此NOBMG具有较低的硫醇反硝化能力键。所述ķ TR，计算所研究的亲核试剂的值，并建立了一个布朗斯台德型积给出意想不到底片β NUC（β NUC（NOBMG）= - 0,17和β NUC（NOTSG）= - 0,11）。非典型β NUC值归因于需要对亲核试剂的前面去溶剂。
• Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols
  作者：Kun Wang、Zhong Wen、Wei Zhang、Ming Xian、Jin-Pei Cheng、Peng George Wang

  DOI：10.1016/s0960-894x(00)00688-0

  日期：2001.2

  Using UV-vis spectrometrical measurements, equilibrium constants for NO transfer between S-nitroso-N-acetyl-penicillamine (SNAP) and different thiols as well as kinetic data for NO transfer from S-nitroso bovine serum albumin (BSANO) to thiols have been obtained, NO transfer from SNAP to other primary/secondary thiols are thermodynamically favorable, whereas other S-nitrosothiols exhibit similar NO transfer potential. The obtained Gibbs free energy, enthalpy and entropy data indicated that NO transfer reactions from SNAP to four thiols are exothermic with entropy loss. The kinetic behavior of BSANO/RSH transfer can be related to both the acidity of sulfhydryl group and the electronic structure in thiol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Barnett, D.Jonathan; Rios, Ana; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1995, # 7, p. 1279 - 1282
  作者：Barnett, D.Jonathan、Rios, Ana、Williams, D. Lyn H.

  DOI：——

  日期：——
• A Convenient Method for Production of Thionitrites and Disulfides Under Mild and Heterogeneous Condition
  作者：Mohammad Ali Zolfigol

  DOI：10.1080/00397910008087194

  日期：2000.4.1

  Thiols can be readily converted to their corresponding thionitrite with a combination of inorganic acidic salts and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.
• Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity
  作者：C. Adam、L. García-Río、J.R. Leis、J.A. Moreira

  DOI：10.1016/j.tet.2006.06.060

  日期：2006.9

  The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (alpha(1g) approximate to -1.30), but virtually independent of the basicity of the thiol (beta(nuc) approximate to 0-10)This dependence is ascribed to the presence of a nucleophile desolvation equilibrium (beta(d)) that is followed by the attack of the thiolate ion on the nitroso group (beta'(nuc)) via a concerted mechanism. The equilibrium constants for the loss of a nitroso group from a nitrosothiol and an N-nitrososulfonarni de were used to obtain the equilibrium constants for the different reactions involved. By using rate-equilibrium correlations, the parameters alpha(norm)(1g) ,beta(d), and beta('norm)(nuc) were obtained. (c) 2006 Elsevier Ltd. All rights reserved.