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

Mohamadighader, Niloofar; Saraei, Mahnaz; Nematollahi, Davood; Goljani, Hamed

doi:10.1039/d0ra05680d

Cited by 8 publications

(2 citation statements)

References 34 publications

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“…Therefore, different parameters were investigated respectively: (1) The distribution of partial charge, which was used to approve the oxidation mechanism of MFA and also to determine the best active site as a nucleophile acceptor in the oxidized form of MFA . (2) Thermodynamic stability of intermediates, which was verified using the relative Gibbs free energy 34 . (3) The Kinetic stability of intermediates was evaluated via the HOMO–LUMO energy gap 24 .…”

Section: Resultsmentioning

confidence: 99%

Green electrochemical method for the synthesis of nitro and azo derivatives based on mefenamic acid

Amooshahi

Khazalpour

Amani

et al. 2022

Sci Rep

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Electrochemical study of mefenamic acid (MFA) was carried out with details in water/ethanol mixture by the various voltammetric techniques. The results showed that the oxidation of MFA is highly dependent on pH and follows the Eir mechanism. The EpA1-pH diagram plotted based on the differential pulse voltammograms shows two linear segments, 66 and 26 mV/pH slope. Also, the diffusion coefficient and the surface excess, Ӷ* of MFA in aqueous buffered solution, determined by using the single potential-step chronoamperometry and chronocoulometry methods. Electrochemical nitration of MFA in an aqueous solution and the presence of nitrite ion (1) were both investigated by the cyclic voltammetry and controlled-potential coulometry techniques. Our results indicate that the oxidized form of MFA participates in a Michael-type addition reaction with nitrite ion (1) to form the corresponding Nitromefenamic acids (MFA-4-NO2 and MFA-5-NO2). Also, in another part, a computational study based on the density functional theory (DFT/B3LYP) was performed for the prediction of the best possible pathway in the nucleophilic addition of nitrite ion (1). The electrochemical reduction of produced nitromefenamic acids was investigated using cyclic voltammetry and controlled-potential coulometry techniques. Eventually, two new azo derivatives have been generated via electroreduction of produced nitromefenamic acids and conduction of diazotization reaction, respectively. Both nitro and azo products are approved as paints.

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Section: Resultsmentioning

confidence: 99%

Green electrochemical method for the synthesis of nitro and azo derivatives based on mefenamic acid

Amooshahi

Khazalpour

Amani

et al. 2022

Sci Rep

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“…Because of its enrichment, low price, and excellent solvent properties, acetonitrile has been widely applied as a common solvent in organic synthesis [4][5][6][7][8]. Acetonitrile is also an important synthetic intermediate and often used as a source of nitrogen for the preparation of typical nitrogen-containing compounds.…”

Section: Introductionmentioning

confidence: 99%

Advances in the Application of Acetonitrile in Organic Synthesis since 2018

Zhong

Zhang²,

Luo

et al. 2023

Catalysts

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Acetonitrile is commonly used as an organic solvent and can also be used as an important intermediate in organic synthesis. Its widespread use has led to the development of new methods for the synthesis of a variety of important compounds. In the past decades, the conversion reactions of acetonitrile as a building block have become one of the most-attractive fields in organic synthesis. Especially in the field of electrochemical conversions involving acetonitrile, due to its good conductivity and environmentally friendly features, it has become a powerful and compelling tool to afford nitrogen-containing compounds or nitrile-containing compounds. In this review, we mainly discuss the research progress involving acetonitrile in the past five years, covering both conventional synthesis methods and electrochemical synthesis. Besides, a detailed discussion of the substrate scope and mechanistic pathways is provided.

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Direct electrosynthesis reactions

Nematollahi,

Alizadeh,

Amani

et al. 2024

Practical Aspects of Electroorganic Synthesis

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

Abstract: Electrochemical oxidation pathway of p-chloroaniline (PCA) in the presence of benzenesulfinic acid (BSA).

Cited by 8 publications

References 34 publications

Green electrochemical method for the synthesis of nitro and azo derivatives based on mefenamic acid

Green electrochemical method for the synthesis of nitro and azo derivatives based on mefenamic acid

Advances in the Application of Acetonitrile in Organic Synthesis since 2018

Direct electrosynthesis reactions

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