%0 Journal Article
%T Consecutive loss of two benzyl radicals from the [M£¿+£¿Na]+ adduct ions of pyrogallol tribenzyl ether and its derivatives
%A Dietmar Kuck
%A Ishtiaq Ahmed
%A Karsten Krohn
%A Matthias Letzel
%A Sandra Heitkamp
%J European Journal of Mass Spectrometry
%@ 1751-6838
%D 2018
%R 10.1177/1469066717729300
%X The electrospray ionization¨Ccollision-induced dissociation mass spectra of nine pyrogallol tribenzyl ethers, 2¨C10, and a catechol dibenzyl ether, 11, that bear various functional groups or larger structural extensions have been studied with respect to the occurrence of a highly characteristic consecutive loss of two benzyl radicals from the sodiated molecular ions, [M£¿+£¿Na]+. It is shown that this specific fragmentation reaction strongly dominates other fragmentation routes, such as loss of carbon monoxide, formaldehyde and water. In addition, elimination of benzaldehyde occurs as a minor fragmentation channel in most cases. In contrast to these aryl¨Cbenzyl ethers, the consecutive two-fold loss of C7H7£¿ is suppressed in the [M£¿+£¿Na]+ ions of dibenzyl ethers derived from multiply benzylated gallocatechin and catechin, where the elimination of benzyl alcohol prevails the primary fragmentation almost completely. The secondary fragmentation of the [M£¿+£¿Na]+ ions, which also comprises the two-fold loss of C7H7£¿, as well as a remarkable primary fragmentation of a flavene-based congener leading to particularly stable sodium-free chromylium product ions is also presented. £¿ Deceased.
%K Electrospray mass spectrometry
%K collision-induced dissociation
%K benzyl aryl ethers
%K benzyl radicals
%K phenoxy radicals
%K homolytic cleavage
%K benzoquinones
%K sodiated molecules
%U https://journals.sagepub.com/doi/full/10.1177/1469066717729300