Z. Abliz et al., ELECTRON-IMPACT MASS-SPECTRA OF POLYCYCLIC AROMATIC-COMPOUNDS WITH SEVERAL TYPES OF PYRIDINOBENZANTHRONE AND BENZOBENZANTHRONE SKELETONS, Organic mass spectrometry, 28(5), 1993, pp. 607-614
Electron impact mass spectra were measured for five isomers of pyridin
obenzanthrones and three isomers of benzobenzanthrones. The fragmentat
ion pattern and intensity of M2+, [M-H]+, [M-CO]i+, [M - CO - H(or 2H)
]i+ and [M - CO - HCN]i+ (i = 1, 2) ions indicated remarkable differen
ces and very interesting features according to the isomers with or wit
hout nitrogen and condensation positions of a pyridino or benzo ring t
o the benzanthrone skeleton. Further, the competition of decomposition
s through [M - H]+, [M - CO]+. or [M - HCN]+. ions was confirmed by th
e observation of metastable ions and the appearance energies of fragme
nt ions. Interesting observations from these results were expulsion of
an H atom in close proximity to the area around an O=C group, a weak
bonding interaction between sp2 C-H and an O=C group, inducing specifi
c hydrogen rearrangement, and characteristic charge localization on he
teroatoms.