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Gas-Phase Arylmethyl Transfer and Cyclodeamination of Argentinated N-Arylmethyl-Pyridin-2-Ylmethanimine

  • Research Article
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Journal of The American Society for Mass Spectrometry

Abstract

In collisional activation of argentinated N-arylmethyl-pyridin-2-ylmethanimine, a neutral molecule of AgNH2 is eliminated, carrying one hydrogen from the methylene and the other one from the ortho position (relative to the ipso carbon) of the aryl ring. Taking argentinated N-benzyl-pyridin-2-ylmethanimine for example, the proposition that the AgNH2 loss results from intramolecular arylmethyl transfer combined with cyclodeamination is rationalized by deuterium labeling experiments, blocking experiments, and theoretical calculations. The structure of the final product ion from loss of AgNH2 was confirmed further by multistage mass spectrometry.

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Acknowledgment

The authors gratefully acknowledge financial support from the National Science Foundation of China (21025207 and 21372199).

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  1. Department of Chemistry, Zhejiang University, 38 Zheda Road, Hangzhou, 310027, China

    Hezhi Sun, Lin Wang & Yuanjiang Pan

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  1. Hezhi Sun
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  2. Lin Wang
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Correspondence to Yuanjiang Pan.

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Sun, H., Wang, L. & Pan, Y. Gas-Phase Arylmethyl Transfer and Cyclodeamination of Argentinated N-Arylmethyl-Pyridin-2-Ylmethanimine. J. Am. Soc. Mass Spectrom. 25, 169–175 (2014). https://doi.org/10.1007/s13361-013-0778-7

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