Kinetics of the reaction of phenyl picrates with phenoxide ions in water. Concerted or stepwise?

Michael R. Crampton; Ian A. Robotham

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Kinetics of the reaction of phenyl picrates with phenoxide ions in water. Concerted or stepwise?

机译：苦味酸苯基酯与水中的酚盐离子反应的动力学。一致还是逐步？

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A kinetic study is reported of the exchange reactions of substituted phenoxide ions with some ring-substituted 2,4,6-trinitrophenyl ethers in water. The βr?nsted diagrams formed by plotting log k, where k is the second-order rate constant for reaction, versus pKa show a distinct change in slope when ΔpK_a=0 (ΔpK_a being the difference in pK_a values of the leaving group and nucleophile). This is consistent with a two-step process involving a discrete σ-adduct intermediate rather than a concerted process. From the measured β values for forward and reverse processes, the overall effective charge map has been constructed.

机译：动力学研究报道了取代的酚盐离子与一些环取代的2,4,6-三硝基苯基醚在水中的交换反应。通过绘制log k形成的βr nsted图，其中k是反应的二级速率常数，相对于pKa在ΔpK_a= 0（ΔpK_a是离去基团和亲核试剂的pK_a值之差）时显示出明显的斜率变化。。这与包含离散σ加合物中间体而不是协同过程的两步过程一致。根据正向和反向过程的测得的β值，可以构建总体有效电荷图。

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《Journal of Physical Organic Chemistry》 |2013年第12期|共6页
作者
Michael R. Crampton; Ian A. Robotham;
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正文语种 eng
中图分类有机化学一般性问题;
关键词
βr?nsted equation; effective charge map; intermediates; nitro-compounds; nucleophilic aromatic substitution;

机译：βr？nsted方程;有效电荷图;中间体;硝基化合物;亲核芳族取代;

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1. Kinetics of the reaction of phenyl picrates with phenoxide ions in water. Concerted or stepwise? [J] . Michael R. Crampton, Ian A. Robotham Journal of Physical Organic Chemistry . 2013,第12期

机译：苦味酸苯基酯与水中的酚盐离子反应的动力学。一致还是逐步？
2. 1 Kinetic Study on Nucleophihc Substitution Reactions of Phenyl Y-Substituted-Phenyl Carbonates with Z-Substituted-Phenoxides: Effect of Modification of Nonleaving Group from Benzoyl to Phenyloxycarbonyl on Reactivity and Reaction Mechanism [J] . Se-Won Min, Min-Young Kim, Ik-Hwan Um Bulletin of the Korean Chemical Society . 2012,第10期

机译：1苯基Y取代的苯基碳酸酯与Z取代的酚盐的核取代反应的动力学研究：苯甲酰基到苯氧羰基的非离去基团的修饰对反应性和反应机理的影响
3. A Kinetic Study on Nucleophilic Substitution Reactions of Phenyl Y-Substituted-Phenyl Carbonates with Z-Substituted-Phenoxides: Effect of Modification of Nonleaving Group from Benzoyl to Phenyloxycarbonyl on Reactivity and Reaction Mechanism [J] . nbsp, Ik-Hwan Um, Min-Young Kim, Bulletin of the Korean Chemical Society . 2012,第10期

机译：苯基Y取代的苯基碳酸酯与Z取代的酚盐的亲核取代反应的动力学研究：苯甲酰基到苯氧羰基的非离去基团的修饰对反应性和反应机理的影响
4. Stepwise and Concerted Electron Transfer/ Bond Breaking Reactions.Similarities and Contrasts in Thermal and Photoinduced processes. [C] . Laurence Pause, Marc Robert, Jean-Michel Saveant The Meeting of the Electrochemical Society . 2001

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5. Computational investigations of singlet biradicals: Concerted and stepwise mechanisms for reactions of ozone with acetylene, butadiene and isoprene. [D] . Weng, Chang'e. 2005

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6. Concerted or Stepwise: How Much Do Free-Energy Landscapes Tell Us about the Mechanisms of Elimination Reactions? [O] . Fernanda Duarte, Scott Gronert, Shina Caroline Lynn Kamerlin, -1

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7. A Kinetic Study on Nucleophilic Substitution Reactions of Phenyl Y-Substituted-Phenyl Carbonates with Z-Substituted-Phenoxides: Effect of Modification of Nonleaving Group from Benzoyl to Phenyloxycarbonyl on Reactivity and Reaction Mechanism [O] . Se-Won Min, Min-Young Kim, Ik-Hwan Um 2012

机译：苯基Y-取代 - 苯基与Z-取代 - 苯氧基碳酸酯的亲核取代反应的动力学研究：从苯甲酰基的非羊烯基改性对苯氧基羰基对反应性和反应机制的影响

Kinetics of the reaction of phenyl picrates with phenoxide ions in water. Concerted or stepwise?

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