ArticleJournal of the American Society for Mass Spectrometry2011
N-centered odd-electron ions formation from collision-induced dissociation of electrospray ionization generated even-electron ions: single electron transfer via ion/neutral complex in the fragmentation of protonated N,N'-dibenzylpiperazines and protonated N-benzylpiperazines.
Article in Journal of the American Society for Mass Spectrometry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- A Combined MS/MS and IMS Study Into the Fragmentation Pathway of Nifedipine.Journal of mass spectrometry : JMS · 2026Article
- Collision-induced dissociation of phenethylamides: role of ion-neutral complexes.Rapid communications in mass spectrometry : RCM · 2017Article
- 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
- Gas-phase fragmentations of anions derived from N-phenyl benzenesulfonamides.Journal of the American Society for Mass Spectrometry · 2013Article
- On the origin of the methyl radical loss from deprotonated ferulic and isoferulic acids: electronic excitation of a transient structure.Journal of the American Society for Mass Spectrometry · 2013Article
- Elimination of benzene from protonated N-benzylindoline: benzyl cation/proton transfer or direct proton transfer?Journal of the American Society for Mass Spectrometry · 2013Article
- Gas-phase chemistry of benzyl cations in dissociation of N-benzylammonium and N-benzyliminium ions studied by mass spectrometry.Journal of the American Society for Mass Spectrometry · 2012Article
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4 authors.
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Abstract
Single electron transfer (SET) via ion/neutral complex (INC) was proposed and confirmed to be the key step in the formation of N-centered odd-electron ions from fragmentation of protonated even-electron ions in the present study. Upon collisional activation, the model compounds, protonated N,N'-dibenzylpiperazine and protonated N-benzylpiperazines initially dissociated to form intermediate INCs consisting of N-benzylpiperazine (or piperazine) and benzyl cation. In these ion/neutral complexes, SET reaction and direct separation as well as other reactions were observed and characterized experimentally and theoretically. Density functional theory calculations demonstrated that the energy requirement for homolysis of the precursor ion was so large that it could not be achieved, whereas the heterolytic dissociation followed by electron transfer via INC was energetically preferred. The SET process occurred only when the radical products were more stable than the separation products. The energy barrier for SET in the compounds studied was roughly estimated by comparison with other competing reactions. When the INC contained electron donor with lower ionization energy and electron acceptor with higher electron affinity, the SET reaction was more efficient.
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