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Gas-phase dissociation of 1,4-naphthoquinone derivative anions by electrospray ionization tandem mass spectrometry

✍ Scribed by Ricardo Vessecchi; Carlos A. Carollo; José N. C. Lopes; Antonio E. M. Crotti; Norberto P. Lopes; Sérgio E. Galembeck

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
189 KB
Volume
44
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

Gas‐phase dissociation pathways of deprotonated 1,4‐naphthoquinone (NQ) derivatives have been investigated by electrospray ionization tandem mass spectrometry (ESI‐MS/MS). The major decomposition routes have been elucidated on the basis of quantum chemical calculations at the B3LYP/6‐31 + G(d,p) level. Deprotonation sites have been indicated by analysis of natural charges and gas‐phase acidity. NQ anions underwent an interesting reaction under collision‐induced dissociation conditions, which resulted in the radical elimination of the lateral chain, in contrast with the even‐electron rule. Possible pathways have been suggested, and their mechanisms have been elucidated on the basis of Gibbs energy and enthalpy values for the anions previously described at each pathway. Copyright © 2009 John Wiley & Sons, Ltd.

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