ArticleJournal of the American Society for Mass Spectrometry2013
Elimination of benzene from protonated N-benzylindoline: benzyl cation/proton transfer or direct proton transfer?
Article in Journal of the American Society for Mass Spectrometry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 30 citations in OpenAlex.
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- Quantification and Confirmation of Fifteen Carbamate Pesticide Residues by Multiple Reaction Monitoring and Enhanced Product Ion Scan Modes via LC-MS/MS QTRAP System.Molecules (Basel, Switzerland) · 2018Article
- Liquid Chromatography Coupled with Linear Ion Trap Hybrid OrbitrapMass Spectrometry for Determination of Alkaloids inMolecules (Basel, Switzerland) · 2018Article
- Intramolecular Halogen Atom Coordinated H Transfer via Ion-Neutral Complex in the Gas Phase Dissociation of Protonated Dichlorvos Derivatives.Journal of the American Society for Mass Spectrometry · 2017Article
- 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
- Intramolecular Halogen Transfer via Halonium Ion Intermediates in the Gas Phase.Journal of the American Society for Mass Spectrometry · 2016Article
- Gas-phase arylmethyl transfer and cyclodeamination of argentinated N-arylmethyl-pyridin-2-ylmethanimine.Journal of the American Society for Mass Spectrometry · 2014Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Collision-induced dissociation (CID) of protonated N-benzylindoline and its derivatives was investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Elimination of benzene was observed besides hydride transfer and electron transfer reactions. D-labeling experiments and accurate mass determinations of the product ions confirm that the external proton is retained in the fragment ion, and the elimination reaction was proposed to be initiated by benzyl cation transfer rather than proton transfer. Benzyl cation transfer from the nitrogen atom to one of the sp(2)-hybridized carbon atoms in the indoline core is the key step, and subsequent proton transfer reaction leads to the elimination of benzene. Density functional theory (DFT)-based calculations were performed and the computational results also support the benzyl cation/proton transfer mechanism. Figure ᅟ
Identifiers
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Registered trials
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