Elimination of Benzene from Protonated N-Benzylindoline: Benzyl Cation/Proton Transfer or Direct Proton Transfer? View Full Text


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Article Info

DATE

2013-03

AUTHORS

Cheng Guo, Lei Yue, Mengzhe Guo, Kezhi Jiang, Yuanjiang Pan

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 More... »

PAGES

381-387

References to SciGraph publications

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  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s13361-012-0561-1

    DOI

    http://dx.doi.org/10.1007/s13361-012-0561-1

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1001173953

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/23361371


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