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首页> 外文期刊>Journal of Physical Organic Chemistry >The mechanism of aromatic nucleophilic substitution reaction between ethanolamine and fluoro-nitrobenzenes: An investigation by kinetic measurements and DFT calculations
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The mechanism of aromatic nucleophilic substitution reaction between ethanolamine and fluoro-nitrobenzenes: An investigation by kinetic measurements and DFT calculations

机译：乙醇胺与氟代硝基苯之间的芳香亲核取代反应机理：动力学测量和DFT计算研究

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摘要

We have studied the kinetics and elucidated the mechanism by DFT calculation of the reaction between ethanolamine (EOA) and 1-fluoro-2,4- dinitrobenzene (DNFB) in acetonitrile and toluene. To determine the contribution of the nitro group, the activation energy of the reaction between ethanolamine and 1-fluoro-2-nitrobenzene (MNFB) vs. DNFB was determined in acetonitrile and calculated by DFT method. Kinetic measurements reveal that the reaction is faster in acetonitrile than in toluene. The reaction follows overall second-order kinetics: first order with respect to both EOA and DNFB which is similar to the results reported for reaction between other primary amines and 1-substituted-2,4-dinitrobenzenes. The calculations by using DFT methods reveal that the mechanism of the reaction involves the formation and decomposition of a Meisenheimer complex (MC). DFT calculations also reveal that the activation energy of the reaction is highest in vacuum and decreases with increasing polarity of the solvent reaching a minimum in acetonitrile. In addition, activation energies obtained by both DFT calculations and experiments show that the reactivity of MNFB is less than that of DNFB showing the effect of the 4-nitro group.
机译：通过DFT计算乙醇胺（EOA）与1-氟-2,4-二硝基苯（DNFB）在乙腈和甲苯中的反应，我们研究了动力学并阐明了机理。为了确定硝基的贡献，在乙腈中测定乙醇胺与1-氟-2-硝基苯（MNFB）对DNFB的反应的活化能，并通过DFT方法计算。动力学测量表明，乙腈中的反应比甲苯中的反应更快。该反应遵循总体的二级动力学：关于EOA和DNFB的一级反应，类似于报道的其他伯胺与1-取代的2,4-二硝基苯之间反应的结果。使用DFT方法进行的计算表明，反应机理涉及Meisenheimer配合物（MC）的形成和分解。 DFT计算还表明，反应的活化能在真空中最高，并且随着溶剂极性的增加而降低，在乙腈中达到最小值。另外，通过DFT计算和实验获得的活化能表明，MNFB的反应性小于DNFB的反应性，显示了4-硝基的作用。

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