ArticleJournal of the American Society for Mass Spectrometry2012
Gas phase decarbonylation and cyclization reactions of protonated N-methyl-N-phenylmethacrylamide and its derivatives via an amide Claisen rearrangement.
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 4 papers.
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Who cites it
4 citing papers in PubMed.
- Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CHJournal of the American Society for Mass Spectrometry · 2019Article
- 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
- Mass spectrometric study of the gas-phase difluorocarbene expulsion of polyfluorophenyl cations via F-atom migration.Journal of the American Society for Mass Spectrometry · 2013Article
- Study of the gas-phase intramolecular aryltrifluoromethylation of phenyl(trifluoromethyl)iodonium by ESI-MS/MS.Journal of the American Society for Mass Spectrometry · 2013Article
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Authors and funding
5 authors.
Funding
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Abstract
Gas phase decarbonylation and cyclization reactions of protonated N-methyl-N-phenylmethacrylamide and its derivatives (M·H(+)) were studied by electrospray ionization-tandem mass spectrometry (ESI-MS/MS). MS/MS experiments of M·H(+) showed product ions were formed by loss of CO, which could only occur with an amide Claisen rearrangement. Mechanisms for the gas phase decarbonylation and cyclization reactions were proposed based on the accurate m/z measurements and MS/MS experiments with deuterated compounds. Theoretical computations showed the gas phase Claisen rearrangement was a major driving force for initiating gas phase decarbonylation and cyclization reactions of M·H(+). Finally, the influence of different phenyl substituents on the gas phase Claisen rearrangement was evaluated. Electron-donating groups at the para-position of the phenyl moiety promoted the gas phase Claisen rearrangement to give a high abundance of fragment ions [M - CO + H](+). By contrast, electron-withdrawing groups on the phenyl moiety retarded the Claisen rearrangement, but gave a fragment ion at m/z 175 by loss of neutral radicals of substituents on the phenyl, and a fragment ion at m/z 160 by further loss of a methyl radical.
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Registered trials
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