Investigation of 4-(nitrophenylamino)pent-3-en-2-ones and 4-(nitrobenzylamino)pent-3-en-2-ones by electron ionization mass spectrometry. Observation of characteristic ortho effects |
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Authors: | Frański Rafał Gierczyk Błazej Fiedorow Piotr Chadyniak Dariusz Urbaniak Włodzimierz |
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Institution: | Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland. franski@main.amu.edu.pl |
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Abstract: | The compounds 4-(phenylamino)pent-3-en-2-ones (1-3) and 4-(benzylamino)pent-3-en-2-ones (4-6) substituted with a nitro group on the aromatic ring were studied by electron ionisation mass spectrometry (EIMS). It was deduced that the compounds 1-3 are converted into the tautomeric 4-(arylimino)pentan-2-one during the EI process. Mass spectrometric decompositions of ortho-substituted derivatives (1 and 4) were found to be different from those observed for meta- and para-isomers. The fragmentation pathways are discussed on the basis of data from linked B/E and B(2)/E scans, mass-analysed ion kinetic energy (MIKE) spectra, accurate mass measurements and isotope labelling. |
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