Evidence of Structure-Selective Fragmentations in the Tandem Mass Spectra of Protonated Hydroxyalkylamino-1,4-Naphthoquinones Formed by Electrospray Ionisation
Restricted accessResearch articleFirst published online October, 2009
Evidence of Structure-Selective Fragmentations in the Tandem Mass Spectra of Protonated Hydroxyalkylamino-1,4-Naphthoquinones Formed by Electrospray Ionisation
The collision-induced dissociation of protonated hydroxyalkylamino-1,4-naphthoquinones depends strongly on the structure of the substituent [NHCH2(CH2)nOH, n = 1–5; or NHCH2CH(CH3)OH] on the quinone ring. Protonated naphthoquinones with an unbranched hydroxypropylamino side chain (n = 2) undergo facile and characteristic CH2O loss, whereas isomeric [M + H]+ ions with a branched hydroxypropylamino side chain do not. When n = 1, CH2O elimination occurs less readily, accompanied by CH3N loss, thus allowing this shorter side chain to be identified. Higher homologous species (n = 3–5) do not expel CH2O, but instead eliminate Cn+1H2nO, Cn+1H2n+2O and (for n = 5) Cn+1H2n+1 O.
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