间甲氧基苯酚阴离子 | 40529-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 间甲氧基苯酚阴离子
• 英文名称: m-methoxyphenol anion
• 英文别名: 3-methoxy-phenol; deprotonated form；3-Methoxyphenolat-anion；3-Methoxyphenolate
• CAS: 40529-20-2
• 化学式: C₇H₇O₂
• 分子量: 123.131
• InChiKey: ASHGTJPOSUFTGB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  间甲氧基苯酚阴离子 在 二氧化氮 作用下， 以 水 为溶剂， 生成 3-Methoxyphenoxyl radical
  参考文献：
  名称：

  取代基对二氧化氯，二氧化氮和三氧合硫酸根（1-）自由基对酚的单电子氧化速率的影响

  摘要：

  DOI：

  10.1021/j100408a063
• 作为产物：
  描述：

  3-甲氧基苯酚 以 水 为溶剂， 生成 间甲氧基苯酚阴离子
  参考文献：
  名称：

  水中6-甲氧基-2-吡啶酮互变异构的平衡和活化热力学参数

  摘要：

  在中性水中，6-甲氧基-2-吡啶酮的乳酸亚胺-内酰胺平衡的两个互变异构体的相互转化基本上是通过与pH无关的过程进行的。温度对这种互变异构平衡的位置和动力学的影响已通过温度跳跃弛豫动力学进行了研究。获得的平衡和活化热力学参数（ΔH °26.8 kJ mol –1，ΔS °58 JK –1 mol –1；内酰胺→内酰胺，ΔH c • 46 kJ mol –1，ΔS c • –40 JK – 1摩尔–1）表示动力学熵项的较高值。这些结果表明，互变机理是离子的（而不是协同作用的），并且涉及处于环状过渡态的底物的阴离子形式。在这种过渡状态下，至少两个溶剂分子将暂时确保发生互变异构的位点之间的氢键连接。

  DOI：

  10.1039/p29830000979

文献信息

• Nucleophilicity of phenolates in the reaction with p-nitrophenyl acetate in ethanol
  作者：Giuseppe Guanti、Giorgio Cevasco、Sergio Thea、Carlo Dell'Erba、Giovanni Petrillo

  DOI：10.1039/p29810000327

  日期：——

  of p-nitrophenol in the reaction of nine substituted phenolates with p-nitrophenyl acetate has been determined by spectrophotometric measurements in absolute ethanol at 22°. The phenolate anion is the reactive species and competes with ethoxide anion, arising from solvolysis of the phenolate, for nucleophilic attack on the ester carbonyl carbon atoms. From the observed reaction rates the solvolysis constants

  在22°C的无水乙醇中通过分光光度法测定了九种取代酚盐与对硝基苯乙酸酯反应中对硝基苯酚的释放速率。酚盐阴离子是反应性物质，并且与酚盐的溶剂分解产生的乙氧化物阴离子竞争，对酯羰基碳原子进行亲核攻击。从观察到的反应速率获得酚的溶剂分解常数和p K a值。酚盐阴离子的二阶速率常数与p K a相关相应的苯酚的Bronstedβ值为0.57。进行了与芳基硫醚对乙醇中相同底物的亲核反应性的比较。决定速率的步骤可能是芳基硫醚化物反应中离去基团的排出，而苯酚盐反应中亲核试剂的进攻。
• Nucleophilic substitution at a saturated carbon atom with retention of configuration: The reaction of trans-2-halo-3-tert-butyloxiranes with phenolates
  作者：Johann Gasteiger、Karlheinz Kaufmann、Christian Herzig、T.William Bentley

  DOI：10.1016/s0040-4039(00)98728-8

  日期：1985.1

  Whereas reaction of trans-2-chloro or 2-bromo-3-tert-butyloxirane with thiophenolate occurs at C-3 to give 2-phenylmercapto-3,3-dimethylbutanal, phenolates give substitution at C-2 with retention of the oxirane ring and retention of configuration with kinetics that indicate a bimolecular mechanism.

  反式-2-氯或2-溴-3-叔丁基环氧乙烷与硫酚盐在C-3处反应生成2-苯基巯基-3,3-二甲基丁醛，而酚盐在C-2处取代并保留环氧乙烷环并保留具有指示双分子机理的动力学的构型。
• Electrochemistry of Electron-Transfer Probes. The Role of the Leaving Group in the Cleavage of Radical Anions of α-Aryloxyacetophenones¹
  作者：Mogens L. Andersen、N. Mathivanan、Danial D. M. Wayner

  DOI：10.1021/ja954093+

  日期：1996.1.1

  potential (E°) of α-phenoxyacetophenone has been determined from the voltammetric peak potential obtained by linear sweep voltammetry in combination with the rate constant for fragmentation of the radical anion which had been determined by laser flash photolysis. The E° values of a number of α-aryloxyacetophenones were then estimated from a correlation of the 13C chemical shifts of the carbonyl carbon

  α-苯氧基苯乙酮的形式还原电位 (E°) 由线性扫描伏安法获得的伏安峰电位结合激光闪光光解测定的自由基阴离子碎裂速率常数确定。然后根据羰基碳的 13C 化学位移的相关性和一系列取代的 α-苯胺基苯乙酮内的类似相关性（E° 与 13C 化学位移）估计许多 α-芳氧基苯乙酮的 E° 值。使用这些电位（在很宽的取代基范围内仅变化 34 mV），α-芳氧基苯乙酮自由基阴离子碎裂的速率常数由相应伏安波的数字模拟确定。显示碎裂速率常数与相应酚的 pKa 相关。然而，动力学范围太小，实验误差太大，无法区分线性和二次频率...
• Solvent Reorganization as a Governing Factor in the Kinetics of Intramolecular Dissociative Electron Transfers. Cleavage of Anion Radicals of α-Substituted Acetophenones
  作者：Claude P. Andrieux、Jean-Michel Savéant、André Tallec、Robert Tardivel、Caroline Tardy

  DOI：10.1021/ja9622564

  日期：1996.1.1
• Electrochemistry of Electron Transfer Probes. alpha-Aryloxyacetoveratrones and Implications for the Mechanism of Photo-yellowing of Pulp.
  作者：Mogens L. Andersen、Danial D. M. Wayner、Yves Dory、Jean Marc Chapuzet、Jean Lessard、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0830

  日期：——

  Standard potentials (E degrees) of a series of substituted alpha-aryloxyacetoveratrone derivatives have been determined from a correlation of the C-13 NMR chemical shifts of the carbonyl group and a similar correlation (E degrees vs. C-13 NMR shifts) within a series of alpha-anilinoacetoveratrones. Using these potentials the rate constants for fragmentation of the radical anions were determined by digital simulation of the voltammetric waves. The rate contants for C-O cleavage in the radical anions correlate with the pK(a) of the corresponding phenols. The fragmentations are all in the activated region of a general free energy relationship for this class of compound (alpha=0.5). The standard potential and rate constant for fragmention of the alpha-guaiacoxyacetoveratrone radical anion also were determined. This species is a model compound for one of the lignin substructures. The implication of these results on the currently accepted mechanism for photoyellowing of lignin rich paper is discussed.