ArticleJournal of the American Society for Mass Spectrometry2015
Gas-Phase Fragmentation of Protonated N,2-Diphenyl-N'-(p-Toluenesulfonyl)Ethanimidamides: Tosyl Cation Transfer Versus Proton Transfer.
Article in Journal of the American Society for Mass Spectrometry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 9 citations in OpenAlex.
- Revisiting the Fragmentation of Ketoconazole by Positive Electrospray Ionization Tandem Mass Spectrometry and Density Functional Theory Calculations.Rapid communications in mass spectrometry : RCM · 2026Article
- Hydroxyl transferFrontiers in chemistry · 2022Article
- Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CHJournal of the American Society for Mass Spectrometry · 2019Article
- Collision-induced dissociation of phenethylamides: role of ion-neutral complexes.Rapid communications in mass spectrometry : RCM · 2017Article
- Quantification of lactate from various metabolic pathways and quantification issues of lactate isotopologues and isotopmers.Scientific reports · 2017Article
- Fragmentation of Protonated N-(3-Aminophenyl)Benzamide and Its Derivatives in Gas Phase.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
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The gas-phase dissociation chemistry of protonated N,2-diphenyl-N'-(p-toluenesulfonyl) ethanimidamides was investigated by electrospray ionization mass spectrometry in combination with density functional theory calculation. The protonated molecules underwent fragmentation via two main competing channels: (1) migration of the tosyl cation to the anilinic N atom and the subsequent loss of 2-phenylacetonitrile to afford protonated N-phenyl p-toluenesulfonamide (m/z 248); and (2) transfer of the ionizing proton to the anilinic N atom to give an ion/neutral complex of [tosyl cation / 2-phenylacetonitrile] (m/z 272) and the subsequent decomposition to yield tosyl cation (m/z 155). To the best of our knowledge, the gas-phase tosyl cation transfer has not been reported previously. For the para-substituted sulfonamides, the presence of electron-donating groups on the anilinic ring inhibits the reaction channel of the tosyl cation migration, whereas the presence of electron-withdrawing groups favors this pathway.
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Registered trials
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