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Tandem mass spectrometry based investigation of cinnamylideneacetophenone derivatives: valuable tool for the differentiation of positional isomers
Author(s) -
Resende Diana I. S. P.,
Silva Eduarda M. P.,
Barros Cristina,
Domingues M. Rosário M.,
Silva Artur M. S.,
Cavaleiro José A. S.
Publication year - 2011
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.5207
Subject(s) - chemistry , fragmentation (computing) , tandem mass spectrometry , electrospray ionization , tandem , structural isomer , protonation , mass spectrometry , molecule , electrospray , characterization (materials science) , reactivity (psychology) , combinatorial chemistry , computational chemistry , ion , stereochemistry , chromatography , organic chemistry , nanotechnology , medicine , materials science , alternative medicine , pathology , computer science , composite material , operating system
Cinnamylideneacetophenones have been extensively used as versatile starting materials in numerous different transformations. The structural characterization of this type of compounds is, therefore, of crucial importance since it can give information on the chemistry, reactivity and also the potential biological activity of this type of compounds. Thus, 24 derivatives were systematically studied by tandem mass spectrometry (MS 2 ) with electrospray ionization (ESI), in positive ion mode. The protonated molecules, [M + H] + , formed under ESI conditions were induced to dissociate and the fragmentation patterns were studied. The information collected provided important structural information on the type of substituents present and constitute an important database concerning this family of compounds. Overall, it was found that the substitution pattern of the cinnamylideneacetophenone derivatives changes the ESI‐MS 2 fragmentation considerably. These results indicate that ESI‐MS 2 is a useful technique for distinguishing positional isomers of these cinnamylideneacetophenone derivatives. Copyright © 2011 John Wiley & Sons, Ltd.