Anodic oxidation of aniline and N-alkylanilines in aqueous sulphuric acid studied by electrochemical thermospray mass spectrometry

Stassen, I.; Hambitzer, G.

doi:10.1016/s0022-0728(97)80059-9

Cited by 12 publications

(12 citation statements)

References 7 publications

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“…These dimers are further oxidized and recombine to tetramers and so on 39, 40. The odd‐number oligomers are also produced but at significantly lower rates than those with an even number of mers in the chain 41. The presence of trimers as the main products of 2‐methoxyaniline oxidation may reflect the fact that after the formation of dimers, they react with the monomers.…”

Section: Resultsmentioning

confidence: 99%

Polymerization at the gas/solution interface: Preparation of polymer microstructures with gas bubbles as templates

Mazur

Frydrychewicz

2007

J of Applied Polymer Sci

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We report on the chemical polymerization of 2-methoxyaniline at the interface between an aqueous solution and air. The polymer is formed in the interfacial region, whereas the soluble trimer is yielded in the bulk of the polymerization solution. The preferential polymerization of 2-methoxyaniline is discussed in terms of monomer and oligomer accumulation at the interface, which influences the reactivity of these species and allows further polymerization. The phenomenon of polymer growth is employed to selectively deposit polymeric material onto glass slides decorated with gas microbubbles. Because of preferential polymerization at the bubble/solution interface, hemispherical features are produced on the surface of glass. When some polymeric material is mechanically removed, microrings or microholes are obtained. The anomalous polymerization of 2-methoxyaniline is compared to that of 2-methylaniline. This monomer polymerizes uniformly within the entire volume of the reaction mixture; thus, no preferential polymer formation at the gas/solution interface is observed. As a result, deposition on microbubble-decorated glass slides produces polymeric films containing a number of microholes.

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Section: Resultsmentioning

confidence: 99%

Polymerization at the gas/solution interface: Preparation of polymer microstructures with gas bubbles as templates

Mazur

Frydrychewicz

2007

J of Applied Polymer Sci

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“…Hambitzer and co-workers re-visited electrochemistry-mass spectrometry for investigation of the anodic oxidation of aniline in dilute sulfuric acid [67,68] and of N,N-dialkylanilines in neutral aqueous solution [69,70,71]. The use of a dual-beam thermospray ion source enabled the study of reactions in non-aqueous solutions.…”

Section: Redox Reactions In Additional Electrochemical Cellsmentioning

confidence: 99%

“…The arrangement was tested by elucidating the oxidation process of phenothiazine [69]. Further structural information was obtained by use of deuterated aniline [68].…”

Section: Redox Reactions In Additional Electrochemical Cellsmentioning

confidence: 99%

On-line electrochemistry – MS and related techniques

Diehl

Kärst

2002

Anal Bioanal Chem

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This review summarizes publications on the on-line coupling of electrochemistry with mass spectrometry. After a brief historic introduction it is divided into three parts, organized in order of increasing complexity of the experimental arrangement. The first section deals with the use of the electrospray ion source as an electrochemical reactor for oxidation or reduction reactions. It is followed by the second part which covers the hyphenation of different kinds of electrochemical flow cell with a variety of ionization interfaces. The last section focuses on the on-line coupling of chromatographic techniques with electrochemical flow cells and mass spectrometry.

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“…In this study, the potential-dependent formation of dimers and trimers was observed. Later on, Stassen and Hambitzer [26] picked up on this approach. Besides N,Ndimethylaniline, aniline was used in studies focusing on the investigation of the product spectrum.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation and protein adduct formation of aniline: a liquid chromatography/mass spectrometry study

et al. 2012

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Historically, skin sensitization tests are typically based on in vivo animal tests. However, for substances used in cosmetic products, these tests have to be replaced according to the European Commission regulation no. 1223/2009. Modification of skin proteins by electrophilic chemicals is a key process associated with the induction of skin sensitization. The present study investigates the capabilities of a purely instrumental setup to determine the potential of commonly used non-electrophilic chemicals to cause skin sensitization by the generation of electrophilic species from the parent compound. In this work, the electrophiles were generated by the electrochemical oxidation of aniline, a basic industrial chemical which may also be released from azo dyes in cosmetics. The compound is a known sensitizer and was oxidized in an electrochemical thin-layer cell which was coupled online to electrospray ionization-mass spectrometry. The electrochemical oxidation was performed on a boron-doped diamond working electrode, which is able to generate hydroxyl radicals in aqueous solutions at high potentials. Without any pretreatment, the oxidation products were identified by electrospray ionization/time-of-flight mass spectrometry (ESI-ToF-MS) using their exact masses. A mass voltammogram was generated by plotting the obtained mass spectra against the applied potential. Oligomerization states with up to six monomeric units in different redox states of aniline were observed using this setup. This approach was extended to generate adducts between the oxidation products of aniline and the tripeptide glutathione. Two adducts were identified with this trapping experiment. Protein modification was carried out subsequently: Aniline was oxidized at a constant potential and was allowed to react with β-lactoglobulin A (β-LGA) or human serum albumin (HSA), respectively. The generated adducts were analyzed by liquid chromatography coupled to ESI-ToF-MS. For both β-LGA and HSA, aniline adducts were successfully generated and identified.

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Anodic oxidation of aniline and N-alkylanilines in aqueous sulphuric acid studied by electrochemical thermospray mass spectrometry

Cited by 12 publications

References 7 publications

Polymerization at the gas/solution interface: Preparation of polymer microstructures with gas bubbles as templates

Polymerization at the gas/solution interface: Preparation of polymer microstructures with gas bubbles as templates

On-line electrochemistry – MS and related techniques

Electrochemical oxidation and protein adduct formation of aniline: a liquid chromatography/mass spectrometry study

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