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4-氯苯胺在水/乙腈混合物中的电化学研究。一种合成4-氯-2-(苯磺酰基)苯胺和-(4-氯苯基)苯磺酰胺的新方法。

Electrochemical study of 4-chloroaniline in a water/acetonitrile mixture. A new method for the synthesis of 4-chloro-2-(phenylsulfonyl)aniline and -(4-chlorophenyl)benzenesulfonamide.

作者信息

Mohamadighader Niloofar, Saraei Mahnaz, Nematollahi Davood, Goljani Hamed

机构信息

Department of Chemistry, Payame Noor University Tehran Iran.

Faculty of Chemistry, Bu-Ali Sina University Hamedan 65174 Iran

出版信息

RSC Adv. 2020 Aug 26;10(52):31563-31569. doi: 10.1039/d0ra05680d. eCollection 2020 Aug 21.

DOI:10.1039/d0ra05680d
PMID:35520680
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9056402/
Abstract

The electrochemical oxidation of 4-chloroaniline as a model compound in a water/acetonitrile mixture was investigated by cyclic voltammetry and differential pulse voltammetry. It was established that one-electron oxidation of 4-chloroaniline followed by disproportionation reaction affords unstable (4-iminocyclohexa-2,5-dien-1-ylidene)chloronium. In water/acetonitrile mixtures and in the absence of nucleophiles, the most likely reaction on produced chloronium is hydrolysis and -quinoneimine formation. The electrochemical oxidation of 4-chloroaniline in the presence of arylsulfinic acids was also investigated in a water/acetonitrile mixture at a glassy carbon electrode. It was established that under these conditions, the anodically generated chloronium reacts with benzenesulfinic acid to produce the corresponding diaryl sulfone and -phenylbenzenesulfonamide derivatives. In addition, Gaussian 09W was applied for prediction of the possible product by the calculation of natural charge, LUMO orbital energies and thermodynamic stability of intermediates and products.

摘要

通过循环伏安法和差分脉冲伏安法研究了水/乙腈混合体系中作为模型化合物的4-氯苯胺的电化学氧化。已确定4-氯苯胺的单电子氧化随后发生歧化反应会生成不稳定的(4-亚氨基环己-2,5-二烯-1-亚基)氯鎓。在水/乙腈混合体系且不存在亲核试剂的情况下，生成的氯鎓最可能发生的反应是水解并形成对苯醌亚胺。还在水/乙腈混合体系中的玻碳电极上研究了4-氯苯胺在芳基亚磺酸存在下的电化学氧化。已确定在这些条件下，阳极生成的氯鎓与苯亚磺酸反应生成相应的二芳基砜和对苯基苯磺酰胺衍生物。此外，通过计算中间体和产物的自然电荷、最低未占分子轨道（LUMO）轨道能量和热力学稳定性，应用高斯09W软件预测可能的产物。

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