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Fragmentation of 2‐aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry
Author(s) -
Dias Herbert J.,
Vieira Tatiana M.,
Crevelin Eduardo J.,
Donate Paulo M.,
Vessecchi Ricardo,
Crotti Antônio E.M.
Publication year - 2017
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.4024
Subject(s) - chemistry , fragmentation (computing) , electrospray ionization , tandem mass spectrometry , mass spectrometry , halogen , molecule , ion , medicinal chemistry , radical , ionization , computational chemistry , organic chemistry , chromatography , alkyl , computer science , operating system
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–C 6 H 6 ] + , which originated directly from the precursor ion as a result of 2 competitive hydrogen rearrangements. Eliminations of CO and CO 2 from [M+H–C 6 H 6 ] + 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 •CH 3 and CH 2 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 2 CO molecules from B .