ABTS radical cation

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: ABTS radical cation
• 化学式: C₁₈H₁₆N₄O₆S₄
• 分子量: 512.612
• InChiKey: HFNOFNDLBTVECO-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ABTS radical cation 在 高氯酸 、 Fe(water)6(2+) 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Spectroscopic parameters, electrode potentials, acid ionization constants, and electron exchange rates of the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) radicals and ions

  摘要：

  The characteristics of the colorless ABTS2- ion [ABTS - 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonate)] and of the persistent, intensely-colored radical ABTS- have been examined since some reported values are in disagreement. The standard reduction potentials of ABTS-/ABTS2- and ABTS.-/HABTS- are 0.68 and 0.81 V vs NHE, respectively. A second wave in the CV is associated with ABTS.-/ABTS.-, E1/2 = 1/09 V. The pH dependence of E-degrees leads to pK(a)(HABTS-) = 2.2 +/- 0.3; a spectrophotometric pH titration gives 2.08 +/- 0.02 at mu = 1.0 M. The protonated radical HABTS' was not detected (pK(a) < 0), consistent with the higher acidity of the radical relative to its reduced precursor. The EPR spectrum of ABTS.- shows a multiline spectrum centered at g = 2.0036 +/- 0.0004 from the hyperfine coupling to two sets of two equivalent nitrogens as well as six aromatic hydrogens. Line broadening of the methyl and aromatic resonances of ABTS2- in the presence of the radical gives an electron exchange rate constant of (4 +/- 1) x 10(7) L mol-1 s-1 for ABTS2-/ABTS.- in neutral aqueous solution. In 1.0 M perchloric acid, Fe3+ oxidizes HABTS- (k = 1.30 x 10(2) L mol-1 s-1) and Fe2+ reduces ABTS- (k = 7.5 x 10(2)L mol-1 s-1). Although the equilibrium constant K = k(f)/k(r) for the reaction agrees with that predicted by the measured potentials, the individual rate constants are much lower than those one calculates from the Marcus cross-relation, which is typical for reactions of Fe(H2O)63+ and Fe(H2O)62+.

  DOI：

  10.1021/j100127a022
• 作为产物：
  描述：

  在 高氯酸 、 hexaaquairon(III) 作用下， 以 水 为溶剂， 生成 ABTS radical cation
  参考文献：
  名称：

  Spectroscopic parameters, electrode potentials, acid ionization constants, and electron exchange rates of the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) radicals and ions

  摘要：

  The characteristics of the colorless ABTS2- ion [ABTS - 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonate)] and of the persistent, intensely-colored radical ABTS- have been examined since some reported values are in disagreement. The standard reduction potentials of ABTS-/ABTS2- and ABTS.-/HABTS- are 0.68 and 0.81 V vs NHE, respectively. A second wave in the CV is associated with ABTS.-/ABTS.-, E1/2 = 1/09 V. The pH dependence of E-degrees leads to pK(a)(HABTS-) = 2.2 +/- 0.3; a spectrophotometric pH titration gives 2.08 +/- 0.02 at mu = 1.0 M. The protonated radical HABTS' was not detected (pK(a) < 0), consistent with the higher acidity of the radical relative to its reduced precursor. The EPR spectrum of ABTS.- shows a multiline spectrum centered at g = 2.0036 +/- 0.0004 from the hyperfine coupling to two sets of two equivalent nitrogens as well as six aromatic hydrogens. Line broadening of the methyl and aromatic resonances of ABTS2- in the presence of the radical gives an electron exchange rate constant of (4 +/- 1) x 10(7) L mol-1 s-1 for ABTS2-/ABTS.- in neutral aqueous solution. In 1.0 M perchloric acid, Fe3+ oxidizes HABTS- (k = 1.30 x 10(2) L mol-1 s-1) and Fe2+ reduces ABTS- (k = 7.5 x 10(2)L mol-1 s-1). Although the equilibrium constant K = k(f)/k(r) for the reaction agrees with that predicted by the measured potentials, the individual rate constants are much lower than those one calculates from the Marcus cross-relation, which is typical for reactions of Fe(H2O)63+ and Fe(H2O)62+.

  DOI：

  10.1021/j100127a022

文献信息

• New series of quinazolinone derived Schiff’s bases: synthesis, spectroscopic properties and evaluation of their antioxidant and cytotoxic activity
  作者：Zuzana Hricovíniová、Michal Hricovíni、Katarína Kozics

  DOI：10.1007/s11696-017-0345-y

  日期：2018.4

  the basis of their physical and spectral data. The presented microwave-assisted, phosphomolybdic acid (PMoA) catalysed, protocol provides an efficient and convenient route for the synthesis of structurally diverse and potentially biologically active compounds. The molecular structures of these Schiff’s bases related to quinazolinones were confirmed by various spectroscopic methods (NMR, FTIR, UV–Vis)

  一系列新的2,3-二取代-2,3-二氢-喹唑啉-4（1 ħ） -酮衍生的席夫碱（1 - 7）已经被设计，合成和表征其物理和光谱的基础上数据。提出的微波辅助的磷钼酸（PMoA）催化方案为合成结构多样且具有潜在生物活性的化合物提供了一种有效而便捷的途径。这些与喹唑啉酮有关的席夫氏碱的分子结构已通过各种光谱方法（NMR，FTIR，UV-Vis）得以证实，并通过UV-Vis和EPR光谱使用2,2'-azino-bis（3-乙基苯并噻唑啉-6-磺酸）（ABTS）分析。衍生品1 – 7使用3-（4,5-二甲基噻唑-2-基）-2,5-二苯并四唑鎓溴化物（MTT）分析检测体外对人肝癌细胞（HepG2）的细胞毒性。结构与活性之间的关系研究表明，与喹唑啉酮部分相连的官能团的位置和性质会改变其理化和生物学特性。衍生物5，6和7带有多个供电子基团被认为是这个系列中最活跃的成员。
• Spectroscopic parameters, electrode potentials, acid ionization constants, and electron exchange rates of the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) radicals and ions
  作者：Susannah L. Scott、Wen Jang Chen、Andreja Bakac、James H. Espenson

  DOI：10.1021/j100127a022

  日期：1993.6

  The characteristics of the colorless ABTS2- ion [ABTS - 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonate)] and of the persistent, intensely-colored radical ABTS- have been examined since some reported values are in disagreement. The standard reduction potentials of ABTS-/ABTS2- and ABTS.-/HABTS- are 0.68 and 0.81 V vs NHE, respectively. A second wave in the CV is associated with ABTS.-/ABTS.-, E1/2 = 1/09 V. The pH dependence of E-degrees leads to pK(a)(HABTS-) = 2.2 +/- 0.3; a spectrophotometric pH titration gives 2.08 +/- 0.02 at mu = 1.0 M. The protonated radical HABTS' was not detected (pK(a) < 0), consistent with the higher acidity of the radical relative to its reduced precursor. The EPR spectrum of ABTS.- shows a multiline spectrum centered at g = 2.0036 +/- 0.0004 from the hyperfine coupling to two sets of two equivalent nitrogens as well as six aromatic hydrogens. Line broadening of the methyl and aromatic resonances of ABTS2- in the presence of the radical gives an electron exchange rate constant of (4 +/- 1) x 10(7) L mol-1 s-1 for ABTS2-/ABTS.- in neutral aqueous solution. In 1.0 M perchloric acid, Fe3+ oxidizes HABTS- (k = 1.30 x 10(2) L mol-1 s-1) and Fe2+ reduces ABTS- (k = 7.5 x 10(2)L mol-1 s-1). Although the equilibrium constant K = k(f)/k(r) for the reaction agrees with that predicted by the measured potentials, the individual rate constants are much lower than those one calculates from the Marcus cross-relation, which is typical for reactions of Fe(H2O)63+ and Fe(H2O)62+.