<i>Ortho</i>‐hydroxyl effect and proton transfer via ion–neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry

Yue, Lei; Li, Jing; Xie, Xin; Guo, Cheng; Yin, Xiaobo; Yin, Qi; Chen, Yinjuan; Pan, Yuanjiang; Ding, Chuan‐Fan

doi:10.1002/jms.3778

Cited by 3 publications

(3 citation statements)

References 75 publications

(208 reference statements)

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“…It is well known that electron ionization mass spectra of 1,2-disubstituted aromatic compounds are substantially different from those of their positional isomers. There are a number of examples that in ESI conditions the ortho effect also takes place [25][26][27][28][29][30][31].…”

Section: Hplc-ms Analysismentioning

confidence: 99%

Differentiation of bisphenol F diglycidyl ether isomers and their derivatives by HPLC-MS and GC-MS—comment on the published data

et al. 2021

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Positional isomers of bisphenol F diglycidyl ether (BFDGE) have been analyzed by high-pressure liquid chromatography-mass spectrometry and by gas chromatography-mass spectrometry (HPLC-MS, GC-MS). Positional isomers of BFDGE derivatives (BFDGEx2H2O, BFDGExH2OxHCl) have been analyzed by HPLC-MS. On the basis of the obtained fragmentation patterns, the elution order of the isomers has been unequivocally determined, in standard solutions and in the sample of liquid obtained after rinsing an empty mackerel fish can with acetonitrile. Under HPLC condition, para,para isomers are eluted first, then ortho,para isomers’ elution follows, and ortho,ortho isomers are eluted last. Under GC condition, the reverse elution order has been obtained. For the first time, two ortho,para isomers of BFDGExH2OxHCl have been detected and their elution order has been determined. The obtained results are of key importance for determination of the isomer distribution of BFDGE and its derivatives in food samples.

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Section: Hplc-ms Analysismentioning

confidence: 99%

Differentiation of bisphenol F diglycidyl ether isomers and their derivatives by HPLC-MS and GC-MS—comment on the published data

et al. 2021

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“…Fragmentation reaction of organic ions in the gas phase may involve many types of reactive intermediates. Ion neutral complex intermediate [INC] is one of the most interesting and important intermediate that has been widely observed in unimolecular fragmentation reactions in mass spectrometry . An INC consists of the ionic fragment and neutral species that are binding together by electrostatic interactions and maintain their individual mobility.…”

Section: Introductionmentioning

confidence: 99%

“…An INC consists of the ionic fragment and neutral species that are binding together by electrostatic interactions and maintain their individual mobility. In this temporary system, various chemical reactions, such as proton transfer, benzyl cation transfer, electron transfer, hydride transfer, tosyl oxygen transfer, can take place before its final decomposition. So the understanding for formations of INC is one of critical steps for the fragmentation pathways of ionized species…”

Section: Introductionmentioning

confidence: 99%

How Does Azo Bond Cleave in the Gas Phase? Computational and Experimental Study on the Fragmentation Mechanism of Protonated Sudan I

Liang

Wang

et al. 2019

ChemistrySelect

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As a cheap but harmful additive in food industry, 1-phenylazo-2-naphthol (Sudan I) has attracted lots of attentions, which mainly focused on the determinations using the HPLC-ESI-MS/ MS techniques. However, the fragmentation mechanisms are generally scarce. In this paper, the fragmentation pathways of protonated Sudan I in gas-phase were investigated by a combination of electrospray ionization-tandem mass spectrometry and density functional theory (DFT) calculations. Initially, the cleavage of azo bond is triggered by ionizing proton migration from the oxygen atom of O-protonated Sudan I to adjacent N atom through a six-member ring transition state, leading to a single ion-neutral complex (INC-s). Subsequently, the direct decomposition of INC-s gives the naphtol nitrene ion at m/z 156. Meanwhile, INC-s may occur an intermolecular single electron transfer (SET) reaction via the crossing points (INC-mecp), affording the triple ion-neutral complex (INC-t) consisting of naphtol nitrene radical and aniline radical ion. Finally, followed by the decomposition of INC-t, the aniline radical ion at m/z 156 is formed. Further studies on Electrostatic potential map, Natural population analysis (NPA) and frontier molecular orbitals (FMOs) during the proposed mechanism are also found to be in good agreement with experimental observations. Taken together, our results presented here not only provide mechanistic information for better understanding the Sudan I, but also give insights into other related harmful additives in food industry.

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Diastereomer recognition of oxytetracycline and its 4‐epimer by electrospray ionization mass spectrometry and mechanistic investigation

et al. 2019

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Diastereomer recognition of oxytetracycline and its 4-epimer by electrospray ionization mass spectrometry and mechanistic investigation Dear Sir, Tetracyclines (TCs) are a family of antibiotics used in human and veterinary medicine and as animal feed supplement. They are broad-spectrum agents, which show activities against a variety of Gram-positive and Gram-negative bacteria like chlamydia and rickettsia [1]. They are widely used because of the absence of major adverse side effects. The first generation of TCs includes chlortetracycline and oxytetracycline, which were discovered in the late 1940s from natural products. The second generation, such as tetracycline (also discovered from natural sources) and doxycycline (produced by semi-synthesis) came later [2]. However, because of their extensive usage, microbial resistance has emerged [3]. In order to overcome this problem, the third generation of TCs, also called glycylcycline, was discovered [4]. Tegecycline, the first glycylcycline, was first approved by the FDA in 2005 [5]. Structurally speaking, typical TC drugs have four six-membered rings, of which the D ring is aromatic (Figure 1A). In most TCs, the 4-epimers occur as impurities. Previous studies show that 4-epimerization is the favored degradation route for TCs. The 4-epimers could be formed during aqueous storage at mild acidic conditions (pH 2~6

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Ortho‐hydroxyl effect and proton transfer via ion–neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry

Cited by 3 publications

References 75 publications

Differentiation of bisphenol F diglycidyl ether isomers and their derivatives by HPLC-MS and GC-MS—comment on the published data

Differentiation of bisphenol F diglycidyl ether isomers and their derivatives by HPLC-MS and GC-MS—comment on the published data

How Does Azo Bond Cleave in the Gas Phase? Computational and Experimental Study on the Fragmentation Mechanism of Protonated Sudan I

Diastereomer recognition of oxytetracycline and its 4‐epimer by electrospray ionization mass spectrometry and mechanistic investigation

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