Electroreduction mechanism of N-phenylhydroxylamines in aprotic solvents: N-(2-nitrophenyl)- and N-(3-nitrophenyl) hydroxylamines

被引：7

作者：

Mendkovich, Andrey S. ^{[1
]}

Syroeshkin, Mikhail A. ^{[1
]}

Nasybullina, Darya V. ^{[1
]}

Mikhailov, Mikhail N. ^{[1
]}

Gultyai, Vadim P. ^{[1
]}

Rusakov, Alexander I. ^{[2
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] PG Demidov Yaroslavl State Univ, Yaroslavl 150000, Russia

来源：

ELECTROCHIMICA ACTA | 2017年 / 238卷

基金：

俄罗斯科学基金会;

关键词：

N-aryl hydroxylamines; cyclic voltammetry; quantum chemical calculations; radical anion; dissociative electron transfer; DISSOCIATIVE ELECTRON-TRANSFER; ELECTROCHEMICAL REDUCTION; SELF-PROTONATION; MOLECULAR-STRUCTURE; RADICAL-ANIONS; HYDROGEN; BOND; CLEAVAGE; SUBSTITUTION; STEPWISE;

D O I：

10.1016/j.electacta.2017.03.174

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

In continuation of our previous studies on N-(4-nitrophenyl) hydroxylamine (1), we investigated the electroreduction of N-(2- (2) and N-(3-nitrophenyl) hydroxylamines (3) in N, N-dimethylformamide/ Bu4NClO4, using chronoamperometry, cyclic voltammetry, digital simulation and quantum chemical calculations. It was shown that anion radical 3 is rather stable and does not eliminate a hydroxide anion, unlike 2 whose electroreduction mechanism is similar to that previously observed for 1. At the same time, the elimination reaction is observed for dianion of 3 formed at potentials of the first electron transfer by disproportionation of anion radicals. Results of quantum-chemical calculations show that the high stability of anion radical 3 results from the absence of unpaired electron density on its hydroxylamine group. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：9 / 20

页数：12

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