title: Ortho-hydroxyl effect and proton transfer via ion-neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry.
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  = C6 H4  = 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.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Yue
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.|Institute of Biological Engineering, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, Zhejiang, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Xie
authors.affiliation: Cancer Institute, The Second Affiliated Hospital, Zhejiang University School of Medicine, Hangzhou, Zhejiang, 310009, China.
authors.forename: Cheng
authors.initials: C
authors.lastname: Guo
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
authors.forename: Xinchi
authors.initials: X
authors.lastname: Yin
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Yin
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
authors.forename: Yinjuan
authors.initials: Y
authors.lastname: Chen
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
authors.forename: Yuanjiang
authors.initials: Y
authors.lastname: Pan
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
authors.forename: Chuanfan
authors.initials: C
authors.lastname: Ding
keywords: benzyl cation; imine resveratrol analogue; ion-neutral complex; ortho-hydroxyl effect; proton transfer