Ortho‐hydroxyl effect and proton transfer via ion–neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry |
| |
| Authors: | Lei Yue Jing Li Xiaodong Xie Cheng Guo Xinchi Yin Qi Yin Yinjuan Chen Yuanjiang Pan Chuanfan Ding |
| |
| Affiliation: | 1. Department of Chemistry, Zhejiang University, Hangzhou, China;2. Institute of Biological Engineering, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, Zhejiang, China;3. Department of Chemistry, Fudan University, Shanghai, China;4. Cancer Institute, The Second Affiliated Hospital, Zhejiang University School of Medicine, Hangzhou, Zhejiang, China |
| |
| Abstract: | 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, CH2 = C6H4 = 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. |
| |
| Keywords: | imine resveratrol analogue ortho‐hydroxyl effect proton transfer benzyl cation ion– neutral complex |
|
|
