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 fac...

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Bibliographic Details
Published in:European journal of mass spectrometry (Chichester, England) England), 2009-01, Vol.15 (5), p.617-626
Main Authors: Bowen, Richard D., Mahmood, Tariq, Maitland, Derek J., Mercer, Katharine E., Gallagher, Richard T.
Format: Article
Language:English
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Summary: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.
ISSN:1469-0667
1751-6838
DOI:10.1255/ejms.1023