p-phenylphenolate | 46184-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-phenylphenolate
• 英文别名: p-Biphenyloxid；biphenyl-4-ol; deprotonated form；4-Phenylphenolate
• CAS: 46184-40-1
• 化学式: C₁₂H₉O
• 分子量: 169.203
• InChiKey: YXVFYQXJAXKLAK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-phenylphenolate 在 azide radical 作用下， 以 水 为溶剂， 生成 4-苯基苯氧基
  参考文献：
  名称：

  Two Channels of Electron Transfer Observed for the Reaction of n-Butyl Chloride Parent Radical Cations with Naphthols and Hydroxybiphenyls

  摘要：

  Pulse radiolysis of naphthols (NpOH) and hydroxybiphenyls (ByOH) in n-butyl chloride (BuCl) at room temperature exhibits electron transfer at a bimolecular rate constant of (1.0-2.8) x 10(10) dm(3) mol(-1) s(-1). The experiments reveal the direct formation of two types of transients: phenol type radical cations (NpOH.+, ByOH(.+)) and phenoxyl type radicals (NpO., ByO(.)). This is explained by a mechanism involving two different electron-transfer channels. The solute radical cations exhibit two optical absorption bands in the 570-650 and 360-460 nm regions and undergo electron transfer with triethylamine and proton transfer with ethanol with bimolecular rate constants of (4-12) x 10(9) and (3-6) x 10(8) dm(3) mol(-1) s(-1), respectively. NpO. and ByO(.) have relatively long lifetimes and show absorption bands in the 340-400 and 470-540 nm regions. By way of comparison, these phenoxyl type radicals are separately generated by pulse radiolysis in aqueous alkaline solution containing sodium azide, i.e., by oxidation of the solutes with N-3(.) radicals. Under these conditions, the phenoxyl radicals decay by second-order kinetics with 2k = (1.2-4.5) x 10(8) dm(3) mol(-1) s(-1). The various modes of formation and decay of the phenolic radical cations are analyzed over a wide range of dose rate and solute concentrations: In comparison to radical cations of one-ring phenols, the increased stability of NpOH.+ and ByOH(.+) is explained by the delocalization of the positive charge over the whole aromatic system, a postulate supported by open-shell quantum chemical calulations.

  DOI：

  10.1021/jp9808431

文献信息

• Ainscough, Eric W.; Bingham, Alistair G.; Brodie, Andrew M., Journal of Chemical Research - Part S
  作者：Ainscough, Eric W.、Bingham, Alistair G.、Brodie, Andrew M.、Englebretsen, Darren R.、Husbands, June M.

  DOI：——

  日期：——
• Transfer of the diethoxyphosphoryl group [(EtO)2PO] between imidazole and aryloxy anion nucleophiles
  作者：Salem A. Ba-Saif、Andrew Williams

  DOI：10.1021/jo00245a015

  日期：1988.5
• Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke
  作者：Steven D. Linton、Teresa Aja、Peter R. Allegrini、Thomas L. Deckwerth、Jose-Luis Diaz、Bastian Hengerer、Julia Herrmann、Kathy G. Jahangiri、Joerg Kallen、Donald S. Karanewsky、Steven P. Meduna、Kip Nalley、Edward D. Robinson、Silvio Roggo、Giorgio Rovelli、Andre Sauter、Robert O. Sayers、Albert Schmitz、Robert Smidt、Robert J. Ternansky、Kevin J. Tomaselli、Brett R. Ullman、Christoph Wiessner、Joe C. Wu

  DOI：10.1016/j.bmcl.2003.12.106

  日期：2004.5

  Structural modifications were made to a previously described acyl dipeptide caspase inhibitor, leading to the oxamyl dipeptide series. Subsequent SAR studies directed toward the warhead, P2, and P4 regions of this novel peptidomimetic are described herein. (C) 2004 Elsevier Ltd. All rights reserved.
• Role of single electron transfer in SN2-type substitution reactions of anions with alkyl halides
  作者：F. G. Bordwell、John A. Harrelson

  DOI：10.1021/jo00281a035

  日期：1989.9
• Two Channels of Electron Transfer Observed for the Reaction of <i>n</i>-Butyl Chloride Parent Radical Cations with Naphthols and Hydroxybiphenyls
  作者：H. Mohan、R. Hermann、S. Naumov、J. P. Mittal、O. Brede

  DOI：10.1021/jp9808431

  日期：1998.7.1

  Pulse radiolysis of naphthols (NpOH) and hydroxybiphenyls (ByOH) in n-butyl chloride (BuCl) at room temperature exhibits electron transfer at a bimolecular rate constant of (1.0-2.8) x 10(10) dm(3) mol(-1) s(-1). The experiments reveal the direct formation of two types of transients: phenol type radical cations (NpOH.+, ByOH(.+)) and phenoxyl type radicals (NpO., ByO(.)). This is explained by a mechanism involving two different electron-transfer channels. The solute radical cations exhibit two optical absorption bands in the 570-650 and 360-460 nm regions and undergo electron transfer with triethylamine and proton transfer with ethanol with bimolecular rate constants of (4-12) x 10(9) and (3-6) x 10(8) dm(3) mol(-1) s(-1), respectively. NpO. and ByO(.) have relatively long lifetimes and show absorption bands in the 340-400 and 470-540 nm regions. By way of comparison, these phenoxyl type radicals are separately generated by pulse radiolysis in aqueous alkaline solution containing sodium azide, i.e., by oxidation of the solutes with N-3(.) radicals. Under these conditions, the phenoxyl radicals decay by second-order kinetics with 2k = (1.2-4.5) x 10(8) dm(3) mol(-1) s(-1). The various modes of formation and decay of the phenolic radical cations are analyzed over a wide range of dose rate and solute concentrations: In comparison to radical cations of one-ring phenols, the increased stability of NpOH.+ and ByOH(.+) is explained by the delocalization of the positive charge over the whole aromatic system, a postulate supported by open-shell quantum chemical calulations.