Methyl Orange anion | 70735-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: Methyl Orange anion
• 英文别名: trans-methyl orange；Methyl Orange
• CAS: 70735-00-1
• 化学式: C₁₄H₁₄N₃O₃S
• 分子量: 304.349
• InChiKey: IETWCRRCPURZOC-FOCLMDBBSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85.16
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methyl Orange anion 在 sodium hydroxide 、 sodium 作用下， 以 水 为溶剂， 生成 methyl orange
  参考文献：
  名称：

  Yoshikawa, Yuko; Terada, Hiroshi, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 8, p. 2759 - 2765

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-methyl orange 以 sodium hydroxide 为溶剂， 生成 Methyl Orange anion
  参考文献：
  名称：

  Effect of β-Cyclodextrin on the Thermal Cis−Trans Isomerization of Azobenzenes

  摘要：

  The cis-trans thermal isomerization of p-methyl red (1), o-methyl red (2), and methyl orange (3) was inhibited by beta-cyclodextrin (beta-CD) at constant pH. Their isomerization rate decreased 4, 8, and 1.67 times, respectively, in a solution containing 0.01 M beta-CD. This effect can be attributed to the formation of an inclusion complex between the substrate and beta-CD which hinders the rotation of the N=N bond. The isomerization rate of methyl yellow (4), 4-(dimethylamino)-4'-methoxy-azobenzene (5), and naphthalene-1-azo[4'-(dimethylamino)benzene] (6) was not affected by beta-CD due to the presence of an organic cosolvent in the solution which displaces the azobenzene from the cavity, and the complex formed is probably equatorial. In addition, the transition state for the isomerization of compounds 1-3 involves rotation and that of 4-6, which have only electron-donating groups, inversion. This latter process brings about less volume change than rotation so it is less hindered by the complexation with beta-CD.

  DOI：

  10.1021/jo951028+

文献信息

• Complexation of Methyl Orange and Tropaeolin 000 No. 2 by β-cyclodextrin dimers
  作者：Carolyn A. Haskard、Bruce L. May、Tomas Kurucsev、Stephen F. Lincoln、Christopher J. Easton

  DOI：10.1039/a603638d

  日期：——

  Spectrophotometric studies of the complexation of Methyl Orange (MO - ) and Tropaeolin 000 No. 2 (TR - ) anions by dimeric N,N′-bis(6 A -deoxy-6 A -β-cyclodextrin)urea (βCD) 2 ur and its oxalamide and succinamide analogues, (βCD) 2 ox and (βCD) 2 su, respectively, are consistent with the predominant formation of complexes of the general formulae (βCD) 2 x·MO - characterized by stability constants K 1 =(1.05±0.04)×10 5 , (1.92±0.04)×10 5 and (2.50±0.02)×10 4 dm3 mol -1 and (βCD) 2 x·TR - characterized by K 1 =(1.39±0.03)×10 4 , (7.4±0.1)×10 3 and (4.60±0.05)×10 3 dm3 mol -1 , in aqueous phosphate buffer at pH 9.0 and 5.5 and 298.2 K. These values are significantly greater than K 1 =2160 and 710 dm3 mol -1 for the β-cyclodextrin complexes, βCD·MO - and βCD·TR - and are indicative of cooperative binding in (βCD) 2 x·MO - and (βCD) 2 x·TR - . The factors affecting complex stability are discussed and comparisons are made with related systems.

  分光光度法研究甲基橙（MO - ）和托帕啉 000 No.2 (TR - ) 阴离子与二聚 N,Nâ²-双(6 A -脱氧-6 A -δ²-环糊精)脲 (δ²CD)2ur及其草酰胺和琥珀酰胺类似物 (δ²CD) 2 ox 和 (δ²CD) 2 su（分别为 (δ²CD) 2 xÂ-MO - 和 (δ²CD) 2 su）的络合研究结果一致，主要形成了通式为 (δ²CD) 2 xÂ-MO - 的络合物，其特征为稳定常数 K 1 =(1.05±0.04)Ã10 5 , (1.92±0.04)Ã10 5 和 (2. 50±0.02)Ã10 5。50±0.02)Ã10 4 dm3 mol -1 和 (βCD) 2 xÂ-TR - 其特征为 K 1 =(1.39±0.03)Ã10 4, (7.4±0.1)Ã10 3 和 (4.60±0.05)Ã10 3 dm3 mol -1 ，在 pH 值为 9.0 和 5.5 以及 298.2 K 的磷酸盐缓冲水溶液中。这些值明显大于δ-环糊精复合物、δ²CDÂ-MO -和δ²CDÂ-TR -的K 1 =2160和710 dm3 mol-1，表明(δ²CD) 2 xÂ-MO -和(δ²CD) 2 xÂ-TR -中存在协同结合。讨论了影响复合物稳定性的因素，并与相关系统进行了比较。
• Yoshikawa, Yuko; Terada, Hiroshi, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 8, p. 2759 - 2765
  作者：Yoshikawa, Yuko、Terada, Hiroshi

  DOI：——

  日期：——
• Effect of β-Cyclodextrin on the Thermal Cis−Trans Isomerization of Azobenzenes
  作者：Ana M. Sanchez、Rita H. de Rossi

  DOI：10.1021/jo951028+

  日期：1996.1.1

  The cis-trans thermal isomerization of p-methyl red (1), o-methyl red (2), and methyl orange (3) was inhibited by beta-cyclodextrin (beta-CD) at constant pH. Their isomerization rate decreased 4, 8, and 1.67 times, respectively, in a solution containing 0.01 M beta-CD. This effect can be attributed to the formation of an inclusion complex between the substrate and beta-CD which hinders the rotation of the N=N bond. The isomerization rate of methyl yellow (4), 4-(dimethylamino)-4'-methoxy-azobenzene (5), and naphthalene-1-azo[4'-(dimethylamino)benzene] (6) was not affected by beta-CD due to the presence of an organic cosolvent in the solution which displaces the azobenzene from the cavity, and the complex formed is probably equatorial. In addition, the transition state for the isomerization of compounds 1-3 involves rotation and that of 4-6, which have only electron-donating groups, inversion. This latter process brings about less volume change than rotation so it is less hindered by the complexation with beta-CD.