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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Fragmentation of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry

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Author(s):
Dias, Herbert J. [1] ; Vieira, Tatiana M. [1] ; Crevelin, Eduardo J. [1] ; Donate, Paulo M. [1] ; Vessecchi, Ricardo [1] ; Crotti, Antonio E. M. [1]
Total Authors: 6
Affiliation:
[1] Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, Av Bandeirantes 3900, BR-14040901 Ribeirao Preto, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Mass Spectrometry; v. 52, n. 12, p. 809-816, DEC 2017.
Web of Science Citations: 6
Abstract

We investigated the gas-phase fragmentation reactions of a series of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The most intense fragment ions were the acylium ions m/z 105 and {[}M+H-C6H6](+), which originated directly from the precursor ion as a result of 2 competitive hydrogen rearrangements. Eliminations of CO and CO2 from {[}M+H-C6H6](+) were also common fragmentation processes to all the analyzed compounds. In addition, eliminations of the radicals center dot Br and center dot Cl were diagnostic for halogen atoms at aromatic ring A, whereas eliminations of center dot CH3 and CH2O were useful to identify the methoxyl group attached to this same ring. We used thermochemical data, obtained at the B3LYP/6-31+G(d) level of theory, to rationalize the fragmentation pathways and to elucidate the formation of E, which involved simultaneous elimination of 2 CO molecules from B. (AU)

FAPESP's process: 13/20094-0 - Evaluation of the anti-parasitary and insecticidal activities of benzofuran derivatives, and study of their gas-phase fragmentation reactions using tandem mass spectrometry
Grantee:Antônio Eduardo Miller Crotti
Support Opportunities: Regular Research Grants
FAPESP's process: 14/23604-1 - Computational chemistry: a tool to studies of mass spectrometry, reactivity and fragmentation/reaction mechanisms of organic compounds
Grantee:Ricardo Vessecchi Lourenço
Support Opportunities: Regular Research Grants