ArticleJournal of the American Society for Mass Spectrometry2014
Intramolecular electrophilic aromatic substitution in gas-phase fragmentation of protonated N-benzylbenzaldimines.
Article in Journal of the American Society for Mass Spectrometry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation.Scientific reports · 2021Article
- Collision-induced dissociation of phenethylamides: role of ion-neutral complexes.Rapid communications in mass spectrometry : RCM · 2017Article
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Authors and funding
4 authors.
Funding
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Abstract
In this study, the gas-phase fragmentations of protonated N-benzylbenzaldimines were investigated by electrospray ionization tandem mass spectrometry (ESI-MS(n)). Upon collisional activation, several characteristic fragment ions are produced and their fragmentation mechanisms are rationalized by electrophilic aromatic substitution accompanied by benzyl cation transfer. (1) For N-(p-methoxybenzylidene)-1-phenylmethanimine, concomitant with a loss of HCN, a product ion at m/z 121 was observed. It is proposed to be generated from electrophilic substitution at the ipso-position by transferring benzyl cation rather than cleavage of the C-N double bond. (2) For N-(m-methoxybenzylidene)-1-phenylmethanimine, a product ion at m/z 209 was obtained, corresponding to the elimination of NH(3) carrying two hydrogens from the two aromatic rings respectively. This process can be rationalized by two sequential electrophilic substitutions and cyclodeamination reaction based on the benzyl cation transfer. Deuterium-labeled experiments, density functional theory (DFT) calculation and substituent effect results also corroborate the proposed mechanism.
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24957300What OpenQuestion holds
Registered trials
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