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

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-C6 H6 ]+ , which originated directly from the precursor ion as a result of two competitive hydrogen rearrangements. Eliminations of CO and CO2 from [M+H-C6 H6 ]+ were also common fragmentation processes to all the analyzed compounds. In addition, eliminations of the radicals •Br and •Cl were diagnostic for halogen atoms at aromatic ring A, whereas eliminations of •CH3 and CH2 O 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 two CO molecules from B.

DOI: 10.1002/jms.4024

Cite this paper

@article{Dias2017FragmentationO2, title={Fragmentation of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry.}, author={Herbert J{\'u}nior Dias and Tatiana M Vieira and Eduardo Jos{\'e} Crevelin and Paulo Marcos Donate and R Vessecchi and Ant{\^o}nio E M Crotti}, journal={Journal of mass spectrometry : JMS}, year={2017} }