苯甲酸阴离子 | 766-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯甲酸阴离子
• 英文名称: benzoate
• 英文别名: benzoate anion；benzoic acid anion；benzene-carboxylate
• CAS: 766-76-7
• 化学式: C₇H₅O₂
• 分子量: 121.115
• InChiKey: WPYMKLBDIGXBTP-UHFFFAOYSA-M

物化性质

• 熔点：
  119 °C
• 物理描述：
  WHITE CRYSTALS OR POWDER.
• 沸点：
  249 °C
• 闪点：
  121 °C c.c.
• 溶解度：
  Solubility in water, g/100ml at 20 °C: 0.29
• 密度：
  Relative density of the vapour/air-mixture at 20 °C (air = 1): 1
• 蒸汽密度：
  Relative vapor density (air = 1): 4.2
• 蒸汽压力：
  Vapor pressure, Pa at 25 °C: 0.1
• 自燃温度：
  570 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 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：

  苯甲酸阴离子 在 氢气 作用下， 生成 cyclohexane carboxylate
  参考文献：
  名称：

  Energetics of product formation during anaerobic degradation of phthalate isomers and benzoate

  摘要：

  Methanogenic enrichment cultures grown on phthalate, isophthalate and terephthalate were incubated with the corresponding phthalate isomer on which they were grown, and a mixture of benzoate and the phthalate isomer, All cultures were incubated with bromoethanosulfonate to inactivate the methanogens in the mixed culture. Thus, product formation during fermentation of the aromatic substrates could be studied. It was found that reduction equivalents generated during oxidation of the aromatic substrates to acetate were incorporated in benzoate under formation of carboxycyclohexane. During Fermentation of the phthalate isomers, small amounts of benzoate were detected, suggesting that the initial step in the anaerobic degradation of the phthalate isomers is decarboxylation to benzoate. Gibbs free energy analyses indicated that during degradation of the phthalate isomers, benzoate, carboxycyclohexane, acetate and molecular hydrogen accumulated in such amounts that both the reduction and oxidation of benzoate yielded a constant and comparable amount of energy of approximately 30 kJ mol(-1). Based on these observations it is suggested that within narrow energetic limits, oxidation and reduction of benzoate may proceed simultaneously. Whether this is controlled by the Gibbs free energy change for carboxycyclohexane oxidation remains unclear. (C) 1999 Federation of European Microbiological Societies. Published by Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0168-6496(99)00022-7
• 作为产物：
  描述：

  苯甲酰氟 在 potassium fluoride 作用下， 以 水 为溶剂， 生成 苯甲酸阴离子
  参考文献：
  名称：

  Inhibition of the hydrolysis of p-(dimethylamino)benzoyl fluoride by potassium fluoride

  摘要：

  DOI：

  10.1021/ja00244a058
• 作为试剂：
  描述：

  3-甲基-2-丁烯醛 、 ethyl 7-methyl-3-oxoocta-4,6-dienoate 在 苯甲酸阴离子 、 苄基三乙基氯化铵 作用下， 生成 ethyl 2,2-dimethyl-6-(4-methylpenta-1,3-dienyl)-2H-pyran-5-carboxylate
  参考文献：
  名称：

  Condensation of ethyl and methyl 4-(triphenylphosphoranylidine)-3-oxobutanoate with enals

  摘要：

  DOI：

  10.1016/s0040-4039(00)96609-7

文献信息

• Cationic micellar effect on the kinetics of the protolysis of aromatic carboxylic acids studied by the ultrasonic absorption method
  作者：Teruyo Isoda、Miyuki Yamasaki、Hiroshige Yano、Takayuki Sano、Shoji Harada

  DOI：10.1039/ft9949000869

  日期：——

  The protolysis of carboxylic acids has been kinetically studied by the ultrasonic absorption method in the presence of tetradecyltrimethylammonium bromide (TTAB) micelles in aqueous solution. The carboxylic acids studied were classified into two categories, one capable of formation of intramolecular hydrogen bond, namely the salicylic acid derivatives (SAD) and the other which cannot form the bond

  在水溶液中存在十四烷基三甲基溴化铵（TTAB）胶束的情况下，通过超声吸收法对羧酸的原位动力学进行了动力学研究。研究的羧酸分为两类，一类能够形成分子内氢键，即水杨酸衍生物（SAD），另一类不能形成该键，即苯甲酸衍生物（BAD）。所述速率常数（γ 2 ķ ˚F，ķ b），表观解离常数（ķ一个），并且将反应（Δ的体积变化V获得）。不同的K a关于分子内氢键的影响讨论了SAD和BAD观察到的速率常数的依赖性。还观察到SAD和BAD的ΔV的p K a依赖性。这些依赖性大于水溶液中的依赖性。该结果归因于胶束溶液和水溶液中水分子在溶质周围的排列方式的变化。
• Reactivities of ester radical anions
  作者：John. Masnovi、Jeanne. Maticic

  DOI：10.1021/ja00223a047

  日期：1988.7

  Decomposition des radicaux anioniques d'acetates de benzoates d'alkyles, de benzyle et de benzhydryle

  Decomposition des radicaux anioniques d'acetates de benzoate d'alkanes, de benzle et de二苯甲基
• Concepts of sterically hindered resonance and buttressing effect: gas-phase acidities of methyl-substituted benzoic acids and basicities of their methyl esters
  作者：Michele Decouzon、Peter Ertl、Otto Exner、Jean Francois Gal、Pierre Charles Maria

  DOI：10.1021/ja00078a052

  日期：1993.12

  Two classical terms «Steric Hindrance to Resonance» and «Buttressing Effect» are revisited on the basis of the gas-phase acidities of nine methyl-substituted benzoic acids and of the gas-phase basicities of their methyl esters, measured using FT-ICR spectrometry. By combining these data with published heats of formation of the neutrals and by using the principle of isodesmic reactions, relative enthalpies

  根据使用 FT-ICR 光谱法测量的九种甲基取代苯甲酸的气相酸度及其甲酯的气相碱度，重新审视了两个经典术语“共振位阻”和“支撑效应” . 通过将这些数据与已公布的中性形成热相结合，并利用等分反应原理，分别评估酸分子、它们的阴离子（去质子化）和质子化阳离子（被质子化形式取代）的相对形成焓。相应的甲酯）。所有物种的能量也在半经验水平 (AM1) 计算
• A Flexible Polyphosphate-Driven Regeneration System for Coenzyme A Dependent Catalysis
  作者：Silja Mordhorst、Alice Maurer、Désirée Popadić、Johanna Brech、Jennifer N. Andexer

  DOI：10.1002/cctc.201700848

  日期：2017.11.23

  exploited owing to the lack of an efficient regeneration system. Here, we report an acyl‐CoA regeneration system with integrated adenosine triphosphate (ATP) regeneration that is based on inexpensive polyphosphate as the single energy source. In the four‐enzyme cascade, two cofactors, acyl‐CoA and ATP, are each regenerated up to 2000 times. The applicability for different acyl donors and acceptors is shown

  辅酶A（CoA）是生化反应中常见的辅因子，依赖于CoA的酶催化合成代谢和分解代谢中的关键步骤。这种复杂的分子在许多高价值产品的合成中也起着重要作用，例如合成抗生素，维生素，信息素和生物聚合物。然而，由于缺乏有效的再生系统，生物催化过程的合成潜力无法得到充分利用。在这里，我们报告了一种基于酰基磷酸三乙腺苷（ATP）再生的酰基辅酶A再生系统，该再生系统基于廉价的多磷酸盐作为单一能源。在四酶级联反应中，两个辅因子酰基辅酶A和ATP分别再生多达2000次。通过HPLC分析显示了对于不同的酰基供体和受体的适用性。
• Hydrogen Bonding Lowers Intrinsic Nucleophilicity of Solvated Nucleophiles
  作者：Xin Chen、John I. Brauman

  DOI：10.1021/ja802814a

  日期：2008.11.12

  The relationship between nucleophilicity and the structure/environment of the nucleophile is of fundamental importance in organic chemistry. In this work, we have measured nucleophilicities of a series of substituted alkoxides in the gas phase. The functional group substitutions affect the nucleophiles through ion-dipole, ion-induced dipole interactions and through hydrogen bonding whenever structurally

  亲核性与亲核试剂的结构/环境之间的关系在有机化学中至关重要。在这项工作中，我们测量了一系列取代醇盐在气相中的亲核性。官能团取代通过离子-偶极子、离子诱导偶极子相互作用和结构上可能的氢键影响亲核试剂。这组醇盐是在微溶剂化设置下研究亲核试剂的理想模型系统。应用马库斯理论来分析结果。使用 Marcus 理论，我们将亲核性分成两个独立的部分，即内在亲核性和仅由总反应放热性决定的热力学驱动力。发现取代醇盐的表观亲核性总是远低于未取代醇盐的亲核性。然而，离子-偶极子、离子诱导的偶极子相互作用本身不会显着影响固有的亲核性。表观亲核性的降低是由于较弱的热力学驱动力造成的。另一方面，氢键不仅可以稳定亲核试剂，还可以将本征势垒高度增加 3 至大约 4 kcal mol (-1)。在这方面，氢键不是作为外部偶极子意义上的扰动，而是更直接地影响亲核醇盐的电子结构和反应性。这一发现让我们更深入地了解溶剂化对亲核性的影响，

表征谱图