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Intramolecular benzyl cation transfer in the gas‐phase fragmentation of protonated benzyl phenyl sulfones
Author(s) -
Yin Qi,
Guo Nian,
Yin Xinchi,
Ma Ge,
Huang Yu,
Pan Yuanjiang
Publication year - 2021
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.4691
Subject(s) - chemistry , protonation , intramolecular force , fragmentation (computing) , dissociation (chemistry) , tandem mass spectrometry , medicinal chemistry , electrospray ionization , ion , mass spectrometry , photochemistry , collision induced dissociation , sulfone , stereochemistry , organic chemistry , chromatography , computer science , operating system
In this study, the gas‐phase fragmentations of protonated benzyl phenyl sulfones were investigated by electrospray ionization tandem mass spectrometry (ESI‐MS n ). Upon collisional activation, several characteristic fragment ions were observed, and the similar results occurred with different substituted benzyl phenyl sulfones. A mechanism involving an intramolecular benzyl cation transfer and the formation of intermediate ion was proposed and further identified by density functional theory (DFT) calculations. In addition, a reference compound, benzenesulfinic acid benzyl ester, has been synthesized, and its protonated ion has the same gas‐phase behavior as compared to the protonated benzyl phenyl sulfone. This work provides access to some insight into the intramolecular benzyl‐transfer reactions of benzyl phenyl sulfones in the gas phase and orients the characteristic peaks in collision‐induced dissociation spectrometry (CID‐MS).