Decarboxylative Coupling Reaction in ESI(−)-MS/MS of 4-Nitrobenzyl 4-Hydroxybenzoates: Triplet Ion–Neutral Complex-Mediated 4-Nitrobenzyl Transfer

doi:10.1007/s13361-016-1339-7

Paper

Decarboxylative Coupling Reaction in ESI(−)-MS/MS of 4-Nitrobenzyl 4-Hydroxybenzoates: Triplet Ion–Neutral Complex-Mediated 4-Nitrobenzyl Transfer

Published Feb 29, 2016 · Xiaoping Zhang, X. Bai, Liwen Fang

Journal of The American Society for Mass Spectrometry

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Abstract

AbstractIn negative electrospray ionization mass spectrometry of 4-nitrobenzyl 4-hydroxybenzoates, a decarboxylation reaction, which was significantly promoted by the presence of a nitro group on the benzyl group, competed with radical elimination reactions. Density functional theory calculations indicated that decarboxylation of deprotonated 4-nitrobenzyl vanillate occurred via a radical route involving homolytic cleavage of the Cbenzyl–O bond to give a triplet ion–neutral complex, followed by decarboxylative coupling. Graphical Abstractᅟ

Study Snapshot

Decarboxylation of 4-nitrobenzyl 4-hydroxybenzoates occurs via a radical route involving homolytic cleavage of the Cbenzyl-O bond, leading to a triplet ion-neutral complex and decarboxylative coupling.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Decarboxylative Coupling Reaction in ESI(−)-MS/MS of 4-Nitrobenzyl 4-Hydroxybenzoates: Triplet Ion–Neutral Complex-Mediated 4-Nitrobenzyl Transfer

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References

Competing benzyl cation transfers in the gas-phase fragmentation of the protonated benzyl phenylalaninates

The benzyl cation prefers to transfer to the phenyl ring via the amino N atom in gas-phase fragmentation of protonated benzyl phenylalaninates, leading to stepwise benzyl cation transfer.

On the Origin of the Methyl Radical Loss from Deprotonated Ferulic and Isoferulic Acids: Electronic Excitation of a Transient Structure

The methyl radical elimination in ferulic and isoferulic acids is due to intramolecular electronic excitation of a transient structure with an elongating C-O bond.

Gas-phase fragmentation of the protonated benzyl ester of proline: intramolecular electrophilic substitution versus hydride transfer.

Protonated benzyl esters of proline undergo fragmentation via three primary channels, with electron-donating substituents favoring path-b and electron-withdrawing ones favoring path-c.

Dissociative benzyl cation transfer versus proton transfer: loss of benzene from protonated N-benzylaniline.

Dissociative benzyl cation transfer, not proton transfer, is the key step for benzene loss in collisional activation of protonated N-benzylaniline.

Flavonoid metabolism: the synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids

This study synthesized phenolic glucuronide 1a-e and sulfate 2a-e derivates as potential reference compounds for studying flavonoid bioactivity and metabolic profiling studies.

Gas-Phase Chemistry of Benzyl Cations in Dissociation of N-Benzylammonium and N-Benzyliminium Ions Studied by Mass Spectrometry

This study reveals that benzyl cations in gas-phase reactions can act as Lewis acids, electron acceptors, and substrates for nucleophilic attack, offering a richer view of their chemical reactions.

Intramolecular charge transfer in the gas phase: fragmentation of protonated sulfonamides in mass spectrometry.

Protonated sulfonamides in mass spectrometry show different ionization energies and charge transfer patterns, with electron-donating groups favoring charge transfer and strong electron-withdrawing groups hindering it.

Hydride transfer reactions via ion-neutral complex: fragmentation of protonated N-benzylpiperidines and protonated N-benzylpiperazines in mass spectrometry.

The ion-neutral complex (INC)-mediated hydride transfer reaction in protonated N-benzylpiperidines and N-benzylpiperazines can be accurately predicted using mass spectrometry, with the distribution of product ions depending on the stabilization energy of the INC.

An experimental and computational study on the dissociation behavior of hydroxypyridine N-oxides in atmospheric pressure ionization mass spectrometry.

The dissociation behavior of hydroxypyridine N-oxides is similar across different atmospheric pressure ionization sources, but differences in fragment intensities allow for the differentiation of the two isomers at collision energies above 13 eV.

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