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

Author(s)

Vessecchi, Ricardo ^[1] ; Carollo, Carlos A. ^[2] ; Lopes, Jose N. C. ^[2] ; Crotti, Antonio E. M. ^[3] ; Lopes, Norberto P. ^[2] ; Galembeck, Sergio E. ^[1]

Affiliation

^[1] Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, BR-14040901 Ribeirao Preto, SP - Brazil

^[2] Univ Sao Paulo, Dept Quim & Fis, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040901 Ribeirao Preto, SP - Brazil

^[3] Univ Franca, Nucleo Pesquisas Ciencias Exatas, Franca, SP - Brazil

• Document type: Journal article
• Source: Journal of Mass Spectrometry; v. 44, n. 8, p. 1224-1233, AUG 2009.
• Web of Science Citations: 20

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 (C) 2009 John Wiley \& Sons, Ltd. (AU)

• FAPESP's process: 05/01572-1 - The use of computational chemistry in chemical processes involved in electrospray ionization
• Grantee: Ricardo Vessecchi Lourenço
• Support Opportunities: Scholarships in Brazil - Doctorate