4-bromobenzoate anion | 16449-27-7

• 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: 4-bromobenzoate anion
• 英文别名: 4-bromobenzoate；p-bromobenzoate；p-bromobenzoate(1-)；4-bromo-benzoic acid; deprotonated form；4-Brom-benzoat-Anion；4-Bromobenzoate ion
• CAS: 16449-27-7
• 化学式: C₇H₄BrO₂
• 分子量: 200.012
• InChiKey: TUXYZHVUPGXXQG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromobenzoate anion 在 水 、 氧气 作用下， 生成 (4-carboxyphenyl)peroxyl radical anion
  参考文献：
  名称：

  Formation and Reactivity of Phenylperoxyl Radicals in Aqueous Solutions

  摘要：

  The reaction of phenyl radicals with oxygen, to produce phenylperoxyl radicals, and the reactions of several phenylperoxyl radicals with a number of organic compounds in aqueous solutions have been studied by pulse radiolysis. Phenyl radicals were produced by reduction of aryl halides with hydrated electrons. The rate constant for the reaction of 4-carboxyphenyl with O-2 was determined from the rate of buildup of the peroxyl radical absorption at 520 nm as a function of [O-2] and found to be 1.6 x 10(9) L mol(-1) s(-1). Phenyl radicals react with 2-PrOH by H abstraction; a rate constants of 4 x 10(6) L mol(-1) s(-1) was determined for 4-carboxyphenyl by competition with the reaction of this radical with O-2. Phenylperoxyl radicals react with 4-methoxyphenolate ions, trolox C (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), ascorbate ions, chlorpromazine, and ABTS [2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate ion)] by one-electron oxidation. The rate constants for such reactions, determined from the rate of formation of the one-electron oxidation product as a function of substrate concentration, were found to be near 10(8)-10(9) L mol(-1) s(-1). The reaction with neutral phenols, however, was much slower and could not be observed under the pulse radiolysis conditions. Phenylperoxyl radicals are found to be much more reactive than methylperoxyl and more reactive than most substituted methylperoxyls, except for the halogen-substituted radicals. Electron-withdrawing substituents at the 4-position of phenylperoxyl increase the fate constant and electron-donating groups decrease the rate constant for oxidation by this radical, in accordance with the Hammett substituent constants.

  DOI：

  10.1021/j100084a017
• 作为产物：
  描述：

  4-溴苯甲酸 以 甲醇 为溶剂， 生成 4-bromobenzoate anion
  参考文献：
  名称：

  Ka Values of Weak Organic Acids in Protic Solvents Obtained from Their First Hyperpolarizabilities in Solution

  摘要：

  The first hyperpolarizabilities (beta) of some weak aromatic organic acids have been measured in protic solvents by the hyper-Rayleigh scattering (HRS) technique at low concentrations. The measured hyperpolarizability (beta(m)) varies between the two extreme limits: the hyperpolarizability of the acid form (beta(HA)) at the lower side and that of the basic form (beta(A-)) at the higher side. The degree of dissociation (alpha) of the acid in a solvent is related to the measured hyperpolarizability, beta(m), by the following relationship: beta(m)(2)=(1-alpha)beta(HA)(2)+alpha beta(A-)(2). The calculated beta's including solvent effects in terms of an Onsager field do not reproduce the experimentally measured hyperpolarizabilities. Other solvent-induced effects like hydrogen bonding and van der Waals interactions seem to influence the first hyperpolarizability and, thus, indirectly the extent of dissociation of these weak acids in these protic solvents.

  DOI：

  10.1021/j100051a014

文献信息

• Novel Chiral Secondary Amine-Amide Catalysts Friedel-Craft Alkylation Reaction
  作者：Kejun Huang、Xuehai Pei、Xiaogang Yin、Zhiming Chen

  DOI：10.14233/ajchem.2017.20269

  日期：——

  A highly efficient catalytic asymmetric Friedel-Crafts alkylation of indole with nitroalkenes using novel chiral secondary amine-amide as catalyst has been developed. Various types of nitroalkylated indoles were obtained in excellent yields (81-93 %) and high enantio-selectivities (up to 95 % ee).

  开发了一种高效的催化不对称Friedel-Crafts烷基化反应，使用新型的手性二级胺-酰胺作为催化剂对吲哚与硝基烯烃进行了反应。获得了多种类型的硝基烷基化吲哚，产率极佳（81-93%），且具有高的对映选择性（最高可达95% ee）。
• The crystal design of polar one-dimensional hydrogen-bonded copper coordination complexes
  作者：Kiyonori Takahashi、Norihisa Hoshino、Takashi Takeda、Koichiro Satomi、Yasutaka Suzuki、Shin-ichiro Noro、Takayoshi Nakamura、Jun Kawamata、Tomoyuki Akutagawa

  DOI：10.1039/c5dt04865f

  日期：——

  interactions of mononuclear Cu(II) complexes in which one H2O, two pyridines (py), and two p-substituted benzoate (p-RBA) ligands (R = F, Cl, Br, I, CH3, and OCH3) were coordinated to a Cu(II) ion, forming a penta-coordinated asymmetric [Cu(II)(p-RBA)2(py)2(H2O)] mononuclear structure with a permanent dipole moment along the direction of the Cu–OH2 coordination axis. Each asymmetric [Cu(II)(p-RBA)2(py)2(H2O)]

  通过调节单核Cu（II）配合物的分子间相互作用来设计具有二次谐波生成（SHG）的极性晶体，其中一个H 2 O，两个吡啶（py）和两个对位取代的苯甲酸酯（p -RBA）配体（R = F，Cl，Br，I，CH 3和OCH 3）与Cu（II）离子配位，形成五配位不对称[Cu（II）（p -RBA）2（py）2（ H 2 O）]沿Cu–OH 2配位轴方向具有永久偶极矩的单核结构。每个不对称[Cu（II）（p -RBA）2（py）2（H 2 O）]络合物形成极性一维氢键链，[Cu（II）（p -RBA）2（py）2（H 2 O）p -RBA配体的非配位羧酸氧原子与H 2 O分子的氢原子之间存在] ∞。极性晶体的形成取决于极性氢键链的排列。每个极性链的平行排列产生极性晶体。p中R基团的化学设计-RBA配体能够调节链间相互作用的大小和晶体极性；使用具有R = Cl，Br，I和OCH 3的p -RBA配体
• NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：Moon Ho-Sang

  公开号：US20100063041A1

  公开（公告）日：2010-03-11

  The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.

  本发明提供了一种新颖的苯丙酸衍生物和一种包含其作为活性成分的PPAR-γ调节剂。本发明的苯丙酸衍生物具有对PPAR-γ功能的调节作用，从而对PPAR介导的疾病或疾病表现出降血糖、降血脂和减少胰岛素抵抗的作用。因此，本发明在预防或治疗糖尿病和代谢性疾病方面具有预防或治疗作用。
• Kinetics of deprotonation of arylnitromethanes by benzoate ions in acetonitrile solution. Effect of equilibrium and nonequilibrium transition state solvation on intrinsic rate constants of proton transfers
  作者：Joseph R. Gandler、Claude F. Bernasconi

  DOI：10.1021/ja00028a032

  日期：1992.1

  Second-order rate constants for benzoate ion promoted deprotonation reactions of (3-nitrophenyl)nitromethane, (4-nitrophenyl)nitromethane, and (3,5-dinitrophenyl)nitromethane have been determined in acetonitrile solution at 25-degrees-C. These data were obtained at low benzoate buffer concentrations (< 0.01 M), utilizing tetraethylammonium benzoate salts, and benzoate ion concentrations corrected for homoconjugation with data previously reported by Kolthoff and Chantooni. Acidity constants in acetonitrile have also been determined: (3-nitrophenyl)nitromethane, pK(a) = 21.7; (4-nitromethyl)nitromethane, pk(a) = 20.6; and (3,5-dinitrophenyl)nitromethane, pK(a) = 19.8. A Bronsted beta(B) value of 0.56 and an alpha(CH) value of 0.79 have been calculated for the benzoate, 3-bromobenzoate, and 4-nitrobenzoate ion promoted reactions of (3,5-dinitrophenyl)nitromethane and for the benzoate ion promoted reactions of (3-nitrophenyl)nitromethane and (3,5-dinitrophenyl)nitromethane, respectively; (4-nitrophenyl)nitromethane deviates negatively from the Bronsted plot due to the resonance effect of the 4-nitro group. The logarithms of the intrinsic rate constants for benzoate promoted deprotonations of (3-nitrophenyl)nitromethane, (4-nitrophenyl)nitromethane, and (3,5-dinitrophenyl)nitromethane are 4.81, 4.58, and 5.27, respectively, and these values are 1.43, 1.70, and 1.30 log units, respectively, higher in acetonitrile than in dimethyl sulfoxide. Transfer activity coefficients from dimethyl sulfoxide (D) to acetonitrile (A) solution, log D(gamma)A for (3-nitrophenyl)nitromethyl anion (0.28), (4-nitrophenyl)nitromethyl anion (0.56), (3-nitrophenyl)nitromethane (0.18), and (4-nitrophenyl)nitromethane (0.16) have been calculated, and log D(gamma) A for benzoic acid (approximately 1.9) and the benzoate ion (approximately 0.25) have been estimated. The solvent effects on the intrinsic rate constants are analyzed within the framework of the Principle of Nonperfect Synchronization (PNS) in terms of contributions by late solvation of the arylnitromethyl anion, late solvation of the benzoic acid (produced as a product of the reaction), early desolvation of the benzoate ion and the arylnitromethane, and by a classical solvent effect. The results are also compared with predictions by a theoretical model recently proposed by Kurz. For the comparison of intrinsic rate constants in water and dimethyl sulfoxide there is good agreement between the Kurz model and the experimental results as well as the PNS analysis, but there is a discrepancy between the results and the predictions of the Kurz model for the comparison of intrinsic rate constants in dimethyl sulfoxide and acetonitrile solutions.
• Ka Values of Weak Organic Acids in Protic Solvents Obtained from Their First Hyperpolarizabilities in Solution
  作者：Paresh Chandra Ray、Puspendu Kumar Das

  DOI：10.1021/j100051a014

  日期：1995.12

  The first hyperpolarizabilities (beta) of some weak aromatic organic acids have been measured in protic solvents by the hyper-Rayleigh scattering (HRS) technique at low concentrations. The measured hyperpolarizability (beta(m)) varies between the two extreme limits: the hyperpolarizability of the acid form (beta(HA)) at the lower side and that of the basic form (beta(A-)) at the higher side. The degree of dissociation (alpha) of the acid in a solvent is related to the measured hyperpolarizability, beta(m), by the following relationship: beta(m)(2)=(1-alpha)beta(HA)(2)+alpha beta(A-)(2). The calculated beta's including solvent effects in terms of an Onsager field do not reproduce the experimentally measured hyperpolarizabilities. Other solvent-induced effects like hydrogen bonding and van der Waals interactions seem to influence the first hyperpolarizability and, thus, indirectly the extent of dissociation of these weak acids in these protic solvents.