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首页> 外文期刊>Chemistry: A European journal >Substituent Effects on the Electrophilic Activity of Nitroarenes in Reactions with Carbanions
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Substituent Effects on the Electrophilic Activity of Nitroarenes in Reactions with Carbanions

机译：碳芳烃反应中取代基对硝基芳烃亲电活性的影响

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摘要

The effect on electrophilic activity of substituents located para, ortho, and meta to the nitro group of nitrobenzenes was determined by using vicarious nucleophilic substitution of hydrogen (VNS) with the carbanion of chloromethyl phenyl sulfone (1) as the model process. Values for the relative activities of substituted nitroarenes are given relative to nitrobenzene, which was taken as the standard. This process was chosen as a model reaction because it meets key criteria, such as the wide range of substituents that can be present on the nitrobenzene ring, a low sensitivity to steric hindrance, and in particular the possibility of ensuring conditions in which the overall relative rates of reaction in competitive experiments are equal to the relative rates of nucleophilic addition. The values of relative rates of addition, which were taken to be a measure of electrophilic activity, were determined by competitive experiments in which pairs of nitroarenes competed for the VNS reaction with carbanion of 1. A comprehensive set of data for effects of substituents on the electrophilic activity of nitroarenes is presented for the first time.
机译：通过将氢（VNS）的取代亲核取代与氯甲基苯基砜的碳负离子（1）进行建模，确定对硝基苯的硝基的对位，邻位和间位的取代基对亲电子活性的影响。给出相对于硝基苯的取代硝基芳烃的相对活性值，将其作为标准。选择该过程作为模型反应是因为它符合关键标准，例如硝基苯环上可能存在的取代基范围广，对位阻的敏感性低，尤其是确保总体相对相对分子质量的条件的可能性。竞争性实验中的反应速率等于亲核加成的相对速率。通过竞争实验确定相对添加速率的值，该相对速率被认为是亲电子活性的度量，在竞争性实验中，成对的硝基芳烃以1的碳负离子竞争VNS反应。硝基芳烃的亲电活性首次出现。

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