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Ortho ‐hydroxyl effect and proton transfer via ion–neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry
Author(s) -
Yue Lei,
Li Jing,
Xie Xiaodong,
Guo Cheng,
Yin Xinchi,
Yin Qi,
Chen Yinjuan,
Pan Yuanjiang,
Ding Chuanfan
Publication year - 2016
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.3778
Subject(s) - chemistry , fragmentation (computing) , imine , protonation , mass spectrometry , tandem mass spectrometry , ion , electrospray ionization , medicinal chemistry , photochemistry , organic chemistry , catalysis , chromatography , computer science , operating system
The fragmentation pathways of protonated imine resveratrol analogues in the gas‐phase were investigated by electrospray ionization–tandem mass spectrometry. Benzyl cations were formed in the imine resveratrol analogues that had an ortho ‐hydroxyl group on the benzene ring A. The specific elimination of the quinomethane neutral, CH 2 = C 6 H 4 = O, from the two isomeric ions [M1 + H] + and [M3 + H] + via the corresponding ion–neutral complexes was observed. The fragmentation pathway for the related meta ‐isomer, ion [M2 + H] + and the other congeners was not observed. Accurate mass measurements and additional experiments carried out with a chlorinated analogue and the trideuterated isotopolog of M1 supported the overall interpretation of the fragmentation phenomena observed. It is very helpful for understanding the intriguing roles of ortho‐hydroxyl effect and ion–neutral complexes in fragmentation reactions and enriching the knowledge of the gas‐phase chemistry of the benzyl cation. Copyright © 2016 John Wiley & Sons, Ltd.