title: Evaluation of the α-phenylvinyl cation as a chemical ionization reagent for the differentiation of isomeric substituted phenols in an ITMS.
abstract: Ion-molecule reactions between the α-phenylvinyl cation and isomeric naturally occurring phenols were investigated using a quadruple ion trap mass spectrometer. The α-phenylvinyl cation m/z 103, generated by chemical ionization from phenylacetylene, reacts with neutral aromatic compounds to form the characteristic species: [M + 103](+) adduct ions and the trans-vinylating product ions [M + 25](+) , which correspond to [M + 103](+) adduct after the loss of benzene. Isomeric differentiation of several ring-substituted phenols was achieved by using collision-induced dissociation of the [M + 103](+) adduct ions. This method also showed to be effective in the differentiation of 4-ethylguaiacol from one of its structural isomers that displays identical EI and EI/MS/MS spectra. The effects of gas-phase alkylation with phenylvinyl cation on the dissociation behavior were examined using mass spectrometry(n) and labeled derivatives. Copyright © 2015 John Wiley & Sons, Ltd.
authors.affiliation: Unit of Drug Sciences, Department of Life and Environmental Sciences, University of Cagliari, Via Ospedale 72, 09124, Cagliari, Italy.
authors.forename: Michela
authors.initials: M
authors.lastname: Begala
mesh_terms: D002412:Cations / Q000737:chemistry*; D007202:Indicators and Reagents; D007536:Isomerism; D010636:Phenols / Q000032:analysis* / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D053719:Tandem Mass Spectrometry; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D002412:Cations; D007202:Indicators and Reagents; D010636:Phenols; D014753:Vinyl Compounds
keywords: 4-ethylguaiacol; ITMS; chemical ionization; isomeric differentiation; substituted phenols; α-phenylvinyl cation