ArticleJournal of the American Society for Mass Spectrometry2012
Gas-phase chemistry of benzyl cations in dissociation of N-benzylammonium and N-benzyliminium ions studied by mass spectrometry.
Article in Journal of the American Society for Mass Spectrometry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 46 citations in OpenAlex.
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- Collision-induced dissociation of phenethylamides: role of ion-neutral complexes.Rapid communications in mass spectrometry : RCM · 2017Article
- Decarboxylative Coupling Reaction in ESI(-)-MS/MS of 4-Nitrobenzyl 4-Hydroxybenzoates: Triplet Ion-Neutral Complex-Mediated 4-Nitrobenzyl Transfer.Journal of the American Society for Mass Spectrometry · 2016Article
- Intramolecular Halogen Transfer via Halonium Ion Intermediates in the Gas Phase.Journal of the American Society for Mass Spectrometry · 2016Article
- Gas-Phase Fragmentation of Protonated N,2-Diphenyl-N'-(p-Toluenesulfonyl)Ethanimidamides: Tosyl Cation Transfer Versus Proton Transfer.Journal of the American Society for Mass Spectrometry · 2015Article
- Intramolecular electrophilic aromatic substitution in gas-phase fragmentation of protonated N-benzylbenzaldimines.Journal of the American Society for Mass Spectrometry · 2014Article
- Gas-phase arylmethyl transfer and cyclodeamination of argentinated N-arylmethyl-pyridin-2-ylmethanimine.Journal of the American Society for Mass Spectrometry · 2014Article
- Elimination of benzene from protonated N-benzylindoline: benzyl cation/proton transfer or direct proton transfer?Journal of the American Society for Mass Spectrometry · 2013Article
- Thermometer Ions, Internal Energies, and In-Source Fragmentation in Ambient Ionization.Mass spectrometry reviewsReview
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In this study, the fragmentation reactions of various N-benzylammonium and N-benzyliminium ions were investigated by electrospray ionization mass spectrometry. In general, the dissociation of N-benzylated cations generates benzyl cations easily. Formation of ion/neutral complex intermediates consisting of the benzyl cations and the neutral fragments was observed. The intra-complex reactions included electrophilic aromatic substitution, hydride transfer, electron transfer, proton transfer, and nucleophilic aromatic substitution. These five types of reactions almost covered all the potential reactivities of benzyl cations in chemical reactions. Benzyl cations are well-known as Lewis acid and electrophile in reactions, but the present study showed that the gas-phase reactivities of some suitably ring-substituted benzyl cations were far richer. The 4-methylbenzyl cation was found to react as a Brønsted acid, benzyl cations bearing a strong electron-withdrawing group were found to react as electron acceptors, and para-halogen-substituted benzyl cations could react as substrates for nucleophilic attack at the phenyl ring. The reactions of benzyl cations were also related to the neutral counterparts. For example, in electron transfer reaction, the neutral counterpart should have low ionization energy and in nucleophilic aromatic substitution reaction, the neutral counterpart should be piperazine or analogues. This study provided a panoramic view of the reactions of benzyl cations with neutral N-containing species in the gas phase.
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