Premium
Gas phase reaction between chromones and solvent in an electrospray ionization source
Author(s) -
Liu Zhen,
Shao Yunlong,
Zhu Guizhen,
Wang Xiayan,
Chai Yunfeng,
Wang Lin
Publication year - 2019
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.4305
Subject(s) - chemistry , deprotonation , electrospray ionization , mass spectrometry , dissociation (chemistry) , chromone , electrospray , methanol , solvent , ion , nucleophile , electron ionization , photochemistry , nucleophilic addition , ionization , analytical chemistry (journal) , organic chemistry , chromatography , catalysis
Chromones were measured by using electrospray ionization mass spectrometry in negative mode. Interestingly, in addition to the deprotonated ion ([M − H] − ), unexpected [M + 17] − and [M + 31] − ions were observed in high intensity when water and methanol were used as the solvent. Chromones with different substitutes were tested. Compared with the deprotonated ion, [M + 17] − and [M + 31] − ions were observed with higher abundances when the C‐3 site of chromones was substituted by electron withdrawing groups. Based on high performance liquid chromatography‐mass spectrometry (LC‐MS), deuterium‐labeling and collisional‐induced dissociation experiments, a covalent gas‐phase nucleophilic addition reaction between chromone and water, and the formation of a noncovalent complex between chromone and methanol were proposed as the mechanism for the observed [M + 17] − and [M + 31] − ions, respectively. Understanding and using these unique gas phase reactions can avoid misannotation when analyzing chromones and their metabolites.