Studies of the polarographic and coulometric behaviour of aromatic nitro-compounds

Vijayalakshamma, SK; Subrahmanya, R. S.

doi:10.1016/s0022-0728(69)80195-6

Cited by 23 publications

(2 citation statements)

References 22 publications

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“…For instance, potentials for reducing the nitrobenzene to phenylhydroxylamine in an EtOH/H 2 O solution vary from −0.255 V (pH 1) up to −0.810 V (pH 13) vs . SCE . Furthermore, also the hydroxylamine/nitroso half‐wave potentials (E 1/2 ) shift to more negative values with increasing pH …”

Section: Nitro Derivativesmentioning

confidence: 95%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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In this review,t he versatile and rich chemistry for the electrochemical reductiono fs ubstrates involving N À Ob onds is surveyed. By the cathodic treatment of nitro,n itroso and other oxygenated organic nitrogen substrates,v ersatile andr eactive intermediates are formed which can be subsequently converted to high value-added products. In many examples,n itrogen heterocycles are selectively formed, but, also depending on the electrolytic conditions, free oximes,n itrones,a mines and other entities can be obtained as well. Ther ecent decades have witnessed twom ajor advances-(i)g oing directly to more complext arget molecules and (ii)c onductingt he electrolysesi nm uch simpler set-ups.Both improvements make the cathodic access of the target compoundsm uch more practical and scalable. 1I ntroduction 2N itro Derivatives 2.1 IntermolecularReactions 2.2 IntramolecularReactions:Synthesis of Heterocycles 3O ximes 4O ther Functionalities 5C onclusions

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Section: Nitro Derivativesmentioning

confidence: 95%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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“…Electrochemical reduction pathway of nitro group varies depending on the media in which the nitro group is being analyzed. Although electrochemical reduction of nitroaromatics has been known for many years, there are disagreements about reduction products and pathways [17][18][19][20]. Interest in nitro group reduction pathways has been renewed more recently.…”

Section: Introductionmentioning

confidence: 99%

Dual Electrode Detection in LC‐EC Analysis of Sanger‐tagged Amino Acids: Electrochemical Reduction of Aromatic Nitro Groups

et al. 2021

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Analysis of amino acids is crucial to protein structure elucidation. Amino acids, amenable to separation by liquid chromatography (LC), can be detected by sensitive detectors used in liquid chromatograph including absorbance, fluorescence or electrochemical detector when derivatized. Derivatization of amino acids using suitable reagents enhances the separation and detection of amino acids using liquid chromatography. Sanger's reagent (1-fluoro-2,4-dinitrobenzene, DNFB) makes amino acids suitable for absorbance detection. However, little has been done in terms of liquid chromatography with electrochemical detection (LC-EC) of the DNFB derivatized amino acids. Furthermore, sensor development based on electrochemistry of nitroaromatics has increased dramatically for explosive detection. Since nitroaromatics are electrochemically active, it is essential to determine the reduction pathway. Cyclic voltammetry (CV), rotating disk electrode (RDE) and rotating ring disk electrode (RRDE) experiments have been performed on nitrobenzene (NB) and N-methyl-2,4-dinitroaniline (NMDNA). The results showed that the nitro group was reduced to hydroxylamine in aqueous solutions by addition of four electrons and four protons per nitro group and the hydroxylamine can be reversibly oxidized into a nitroso by removal of two electrons and two protons. Electrochemical detection of the nitro groups is appropriate for dual electrode detection of DNFB labeled amino acids in which reduction can occur on an upstream electrode and corresponding oxidation of the reduction product occurs on the downstream electrode.

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Äthoxycarbonyl‐Wanderung bei der Reduktion eines o ‐Nitrophenylcarbonats

Grafe

Liebenow

1973

Chem. Ber.

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Die Reduktion von l a rnit mehreren Metallen in saurer Losung liefert die Produkte 3a, 4a und 5 a in Abhdngigkeit vom Redoxpotential des verwendeten Metalls und von der Reaktionstemperatur; mit Na2S2O4 wird 2a erhalten. Es wird ein. Mechanismus diskutiert, der sich auf eine polarographische Untersuchung und auf die Vertcilung der Reduktionsproduktc von l a stutzt. Je wirksamer das Redoxsystem und je hoher die Reaktionstemperatur sind, desto grofler ist die Ausbeute am Benzoxazolon 4a. Ethoxycarbonyl Migration during Reduction of an o-Nitrophenyl CarbonateReduction of l a with several metals in acid solution yields the products 3a, 4a, and 5a, depending on the reduction potential of the metal used and on the reaction temperature; reduction of 1 a with Na2S2O4 yields 2a. A mechanism, bascd on a polarographic study and on the distribution of the products of reduction of l a , is discussed. The more efficient the redox system and the higher the temperature of the reaction are, the better is the yield of benzoxazolone 4a. 1 2 3 4 5 Umlagerungen bei der Darstellung oder Verseifung von N,O-Diacylderivaten von o-Aminophenolen sind lange bekanntl) und werden aueh heute noch bearbeitetz). Walirend N-(2-Hydroxyphenyl)carbamidsaure-athylester 3 aus o-Aminophenolen und Chlorameisen-1) l a )

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Studies of the polarographic and coulometric behaviour of aromatic nitro-compounds

Cited by 23 publications

References 22 publications

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Dual Electrode Detection in LC‐EC Analysis of Sanger‐tagged Amino Acids: Electrochemical Reduction of Aromatic Nitro Groups

Äthoxycarbonyl‐Wanderung bei der Reduktion eines o ‐Nitrophenylcarbonats

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