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.
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.
Frański
Rafał
R
Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland. franski@main.amu.edu.pl
Gierczyk
Błazej
B
Fiedorow
Piotr
P
Chadyniak
Dariusz
D
Urbaniak
Włodzimierz
W
D000475:Alkenes / Q000032:analysis*; D009574:Nitro Compounds / Q000032:analysis*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013237:Stereoisomerism
D000475:Alkenes; D009574:Nitro Compounds