Gas-Phase Chemistry of Benzyl Cations in Dissociation of N-Benzylammonium and N-Benzyliminium Ions Studied by Mass Spectrometry View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2012-05

AUTHORS

Yunfeng Chai, Lin Wang, Hezhi Sun, Cheng Guo, Yuanjiang Pan

ABSTRACT

In this study, the fragmentation reactions of various N-benzylammonium and N-benzyliminium ions were investigated by electrospray ionization mass spectrometry. In general, the dissociation of N-benzylated cations generates benzyl cations easily. Formation of ion/neutral complex intermediates consisting of the benzyl cations and the neutral fragments was observed. The intra-complex reactions included electrophilic aromatic substitution, hydride transfer, electron transfer, proton transfer, and nucleophilic aromatic substitution. These five types of reactions almost covered all the potential reactivities of benzyl cations in chemical reactions. Benzyl cations are well-known as Lewis acid and electrophile in reactions, but the present study showed that the gas-phase reactivities of some suitably ring-substituted benzyl cations were far richer. The 4-methylbenzyl cation was found to react as a Brønsted acid, benzyl cations bearing a strong electron-withdrawing group were found to react as electron acceptors, and para-halogen-substituted benzyl cations could react as substrates for nucleophilic attack at the phenyl ring. The reactions of benzyl cations were also related to the neutral counterparts. For example, in electron transfer reaction, the neutral counterpart should have low ionization energy and in nucleophilic aromatic substitution reaction, the neutral counterpart should be piperazine or analogues. This study provided a panoramic view of the reactions of benzyl cations with neutral N-containing species in the gas phase. More... »

PAGES

823-833

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  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s13361-012-0344-8

    DOI

    http://dx.doi.org/10.1007/s13361-012-0344-8

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1026886072

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/22367690


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