Corona discharge-induced reduction of quinones in negative electrospray ionization mass spectrometry

Pei, Jiying; Hsu, Cheng-Chih; Wang, Yinghui; Yu, Kefu

doi:10.1039/c7ra08523k

Cited by 21 publications

(9 citation statements)

References 36 publications

(42 reference statements)

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“…60 Similarly, the detected benzenediol peaks (m/z 109.0284), which have retention times >5 min, might be produced from the transformation of the mother compounds by corona discharge. 61 However, those hydrophilic compounds were assuredly generated because the evident signals were found at early retention times (<5 min; note that we confirmed that the catechol peak was positioned at 5 min). Hydroxynitrobenzoic acid (m/z 182.0090) can be generated through two pathways: hydroxylation-first nitration-after, or vice versa.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

Ahn

Kim

2021

Environ. Sci. Technol.

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We investigated benzoic acid oxidation via the reaction of hydrogen peroxide (H2O2) and nitrite (NO2 –). The oxidation of benzoic acid by reactive nitrous acid (HONO) was negligible, and the reactivity of the H2O2/NO2 – system decreased with a decrease in temperature under aqueous conditions. However, freezing markedly accelerated the chemical reaction. Based on Raman microscope measurements, concentrated species were confirmed in certain regions of the ice. We proposed that the change in nitrite speciation (accordingly, a decrease in the pH below pK a), derived from the freezing concentration effect, was the reason for the accelerated reactions. The oxidation characteristics of the system were monitored under varying conditions, such as initial pH, dosage ratio, benzoic acid concentration, and reaction with various benzene derivatives. The ultrahigh-performance liquid chromatography/electrospray ionization/mass spectrometry (UHPLC/ESI/MS) measurement showed that peroxynitrous acid (HOONO)-mediated oxidation generated hydroxylated and nitrated byproducts. Additionally, decarboxylated products were detected, indicating direct electron transfer from the organic compounds to HOONO. As freezing is a global phenomenon, and H2O2 and NO2 – are ubiquitous in the environment, the transformation of aromatic compounds with H2O2/NO2 – in cold environments must be considered in environmental chemistry.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

Ahn

Kim

2021

Environ. Sci. Technol.

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“…A clean mass spectrum showing a single peak of the C 6 O 6 H – anion is obtained and presented in Figure b. It is not uncommon to observe the [M + H] − anion of quinone-based molecules using ESI sources. , Even though the neutral C 6 O 6 molecule has a high electron affinity of 3.785 eV, we did not observe the signal from the C 6 O 6 •– anion radical. ESI is a relatively high-energy ion source that might hamper the observation of the relatively unstable open-shell C 6 O 6 •– anion.…”

mentioning

confidence: 82%

Revisiting the Hitherto Elusive Cyclohexanehexone Molecule: Bulk Synthesis, Mass Spectrometry, and Theoretical Studies

Zhang

Lü

Wang

et al. 2021

J. Phys. Chem. Lett.

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The cyclohexanehexone (C6O6) octahydrate molecule was claimed to be synthesized as early as 1862. However, the chemical in the 1862 study and the chemicals used in most of the existing studies and sold by most chemical vendors are actually dodecahydroxycyclohexane dihydrate (C6(OH)12·2H2O). Here we revisit our bulk synthesis method of C6O6 by the dehydration of the C6(OH)12·2H2O material, and report the mass spectrum of C6O6 that has been highly challenging to obtain owing to its high sensitivity toward ambient conditions. A new home-built electrospray ionization mass spectrometry setup in a glovebox is utilized to detect C6O6 in the form of C6O6H–. Tandem mass spectrometry MS n (n = 2–4) presents consecutive losses of CO molecules, further confirming the structure of C6O6. Theoretical calculations are performed to recover the chemical bonding of C6O6 and to rationalize the synthetic method. This work provides a benchmark understanding of the historically elusive C6O6.

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“…Stocks and Melanson [38] also published a study demonstrating that the corona discharge was the reason for the in-source reduction of disulfides in formate containing solutions. Similarly, Pei and coworkers demonstrated corona discharge was also responsible for the reduction of quinones in negative ion mode ESI-MS. [39] Overall, the controlled-current electrochemical capabilities of ESI facilitate the ion formation of reactants, intermediates and products that are beneficial to the qualitative and quantitative analysis by mass spectrometry.…”

Section: Esi As a Controlled-current Electrochemical Cellmentioning

confidence: 99%

Recent Advances of In‐Source Electrochemical Mass Spectrometry

et al. 2021

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Hyphenation of electrochemistry (EC) and mass spectrometry has become a powerful tool to study redox processes. Approaches that can achieve this hyphenation include integrating chromatography/electrophoresis between electroinduced redox reactions and detection of products, coupling an EC flow cell to a mass spectrometer, and performing electrochemical reactions inside the ion source of a mass spectrometer. The first two approaches have been well reviewed elsewhere. This Minireview highlights the inherent electrochemical properties of many mass spectrometry ion sources and their roles in the coupling of electrochemistry and mass spectrometric analysis. Development of modified ion sources that allow the compatibility of electrochemistry with ionization processes is also surveyed. Applications of different in-source electrochemical devices are provided including intermediate capturing, bioanalytical studies, nanoparticle formation, electrosynthesis, and electrode imaging.

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Corona discharge-induced reduction of quinones in negative electrospray ionization mass spectrometry

Abstract: Quinone reduction during negative ESI MS was illustrated to be closely related to corona discharge (CD).

Cited by 21 publications

References 36 publications

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

Revisiting the Hitherto Elusive Cyclohexanehexone Molecule: Bulk Synthesis, Mass Spectrometry, and Theoretical Studies

Recent Advances of In‐Source Electrochemical Mass Spectrometry

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