1-oxido-1,2-benziodoxol-3(1H)-one | 84280-67-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-oxido-1,2-benziodoxol-3(1H)-one
• 英文别名: o-iodosobenzoate；1-Oxido-1lambda3,2-benziodoxol-3-one；1-oxido-1λ3,2-benziodoxol-3-one
• CAS: 84280-67-1
• 化学式: C₇H₄IO₃
• 分子量: 263.011
• InChiKey: AIQCMHZOGZINJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxido-1,2-benziodoxol-3(1H)-one 、 4-硝基苯基乙酸酯 以 二甲基亚砜 为溶剂， 生成 1-乙酸基-1,2-苯碘酰-3-(1H)-酮
  参考文献：
  名称：

  酰氧基碘丁烷的化学，碘代苯甲酸酯的中间体催化活性酯的裂解

  摘要：

  可以在二甲基亚砜中直接观察到乙酸-硝基苯酯的碘代苯甲酸酯裂解中的1-乙酰氧基-1,2-苯并三唑-3（1H）-中间体。

  DOI：

  10.1016/s0040-4039(00)95699-5
• 作为产物：
  描述：

  2-碘苯甲酸甲酯 在 hydroxide 、 氯 作用下， 生成 1-oxido-1,2-benziodoxol-3(1H)-one
  参考文献：
  名称：

  酰氧基碘丁烷的化学，碘代苯甲酸酯的中间体催化活性酯的裂解

  摘要：

  可以在二甲基亚砜中直接观察到乙酸-硝基苯酯的碘代苯甲酸酯裂解中的1-乙酰氧基-1,2-苯并三唑-3（1H）-中间体。

  DOI：

  10.1016/s0040-4039(00)95699-5
• 作为试剂：
  描述：

  (4-硝基苯基)二苯基磷酸酯 在 cationic polymer colloid TBAQ₂₄ 、 TAPS buffer 、 1-oxido-1,2-benziodoxol-3(1H)-one 作用下， 生成 对硝基苯酚 、 磷酸二苯酯
  参考文献：
  名称：

  Acceleration of o-Iodosobenzoate-Catalyzed Hydrolysis of p-Nitrophenyl Diphenyl Phosphate by Cationic Polymer Colloids

  摘要：

  Cross-linked polystyrene latexes containing (styrylmethyl)trialkylammonium chloride repeat units greatly accelerate the o-iodosobenzoate (IBA) catalyzed hydrolysis of p-nitrophenyl diphenyl phosphate (PNPDPP). The half-life of PNPDPP is as short as 3 s with 0.10 mg mL(-1) of particles containing 24 mol % of (styrylmethyl)tributylammonium chloride repeat units (TBAQ24) and 4 x 10(-5) M IBA in TAPS buffer at pH 9.1 and 25.0 degrees C, and the apparent second-order rate constant (k(IBA)) exceeds that in the absence of latexes by 6300 times, the largest rate enhancement reported for IBA-catalyzed hydrolysis of PNPDPP in any colloidal or polymeric medium. The k(IBA) value increases with increasing radius of the quaternary ammonium ion (trimethyl < triethyl < tripropyl < tributyl) and with decreasing mole % of (styrylmethyl)trimethylammonium chloride (TMAQ) repeat units in the latexes. The amounts of IBA and chloride ions bound to latexes were measured directly by UV spectrophotometry and chloride-selective electrode analysis of ultrafiltrates from dispersions, and ion exchange selectivity coefficients for IBA and TAPS anions relative to chloride were calculated. The sizes of water-swollen particles were measured by dynamic and static light scattering. Using an ion-exchange model, the second-order rate constants k(2L) in the latex phase were estimated from observed rate constants, the percent of IBA bound, and the particle volumes. The 6300 times rate enhancement in the TBAQ24 dispersion is due ten times to a higher intraparticle rate constant and 630 times to higher local concentrations of IBA and PNPDPP in the latex phase. With the most hydrophilic TMAQ latex particles, the rate enhancements are due entirely to higher reactant concentrations in the particles. The intraparticle rate constants at pH 9.1 and the ion exchange selectivity coefficients can be used to predict rate constants as functions of pH, amount of latex particles, and amount of added NaCl.

  DOI：

  10.1021/ja00088a011

文献信息

• Kinetics and mechanisms of the reactions of benzoyl derivatives of nucleophiles: dependence of the solvation requirement of the reaction on the structures of the nucleophile and the acyl group
  作者：Omar A. El Seoud、Monica Ferreira、Wagner A. Rodrigues、Marie-Fran�oise Ruasse

  DOI：10.1002/poc.864

  日期：2005.2

  desolvation of the entering nucleophile contribute to the OH−-mediated reaction; (ii) the negative and positive signs of ΔS≠ indicate large differences in solvation of the transition states of the kO and kOH pathways. For the spontaneous decomposition of ArCO-Phos, sizeable substituent effects on both ΔH≠ and ΔS≠ were observed. This shows the contribution of solvation of the leaving benzoate and substituent-induced

  研究了亲核试剂的两个系列苯甲酰基衍生物的反应，并将其与N-苯并咪唑的反应结果进行了比较。通用结构为ArCO-Nu，其中Ar ＝ XC 6 H 4-和/或X 2 -C 6 H 3-；X ＝ 4-Me，H，4-Cl，4-CN，4-NO 2，X 2  ＝ 3，5-二硝基。Nu =碘代苯甲酸酯ArCO-Iba和磷酸二阴离子ArCO-Phos。催化速率常数，动力学溶剂同位素效应，动力学取代基效应（哈米特方程）和Δ的依赖性ħ ≠和Δ小号≠上σ X被确定。对于ArCO-Iba，水解通过两条途径发生，即未催化的（k O）和特定的碱催化的（k OH）水攻击碘代苯甲酸酯环的碘原子。该结论基于对ArCO-Iba上的部分电荷的理论计算，以及分别在25°C，k O和k OH下于-0.22和0.92处计算出的小ρ值。ArCO-Phos反应的数据与解离过渡态一致，从而消除了偏磷酸单阴离子（PO）。讨论了机理途径对亲核试剂的依赖性。两个结果是相关的ARCO
• Nucleophilic reactions in zwitterionic micelles of amine oxide or betaine sulfonate surfactants
  作者：Clifford A. Bunton、Marutirao M. Mhala、John R. Moffatt

  DOI：10.1021/j100339a061

  日期：1989.1
• Reduction ofo-iodosobenzoate ion by sulfides and its oxidative regeneration
  作者：Clifford A Bunton、Houshang J Foroudian、Nicholas D Gillitt

  DOI：10.1002/(sici)1099-1395(199910)12:10<758::aid-poc200>3.0.co;2-a

  日期：1999.10

  o-Iodosobenzoate and o-iodoxybenzoate ion (IBA and IBX, respectively) are turnover catalysts of hydrolyses of phosphonofluoridates and non-toxic simulants. Reactions of IBA with phosphonothioates are stoichiometric because sulfides (e.g. 4-methoxybenzenethiol) reduce IBA to o-iodobenzoate ion. Oxidants, e.g. HSO5-, as OXONE, and magnesium peroxyphthalate, MPPA, regenerate IBA and gradually oxidize it to IBX, which eventually decomposes. The procedure was tested on hydrolyses of p-nitrophenyl diphenylphosphate (pNPDPP) and 4-nitrobenzenesulfonyl fluoride, 1, catalyzed by IBA, and the catalyzed hydrolysis of 1 was examined. Some of the oxidation products of 4-methoxybenzeue thiol were identified by H-1 NMR spectroscopy and oxidative decomposition of IBX was monitored. Periodate ion slowly oxidized o-iodobenzoate ion to IBA and IBX. Copyright (C) 1999 John Wiley & Sons, Ltd.