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Electron impact mass spectra of polycyclic aromatic compounds with several types of pyridino‐ and benzobenzanthrone skeletons
Author(s) -
Abliz Zeper,
Aoki Junji,
Ueda Toyotoshi,
Kan Teruo,
Takekawa Minoru,
Iwashima Satoshi
Publication year - 1993
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210280523
Subject(s) - chemistry , heteroatom , fragmentation (computing) , ion , mass spectrum , electron ionization , hydrogen atom , metastability , crystallography , spectral line , stereochemistry , ring (chemistry) , group (periodic table) , ionization , organic chemistry , physics , astronomy , computer science , operating system
Electron impact mass spectra were measured for five isomers of pyridinobenzanthrones and three isomers of benzobenzanthrones. The fragmentation pattern and intensity of M 2+ , [M – H] + , [M – CO] i + , [M – CO – H(or 2H)] i + and [M – CO – HCN] i + ( i = 1, 2) ions indicated remarkable differences and very interesting features according to the isomers with or without nitrogen and condensation positions of a pyridino or benzo ring to the benzanthrone skeleton. Further, the competition of decompositions through [M – H] + , [M – CO] +˙ or [M – HCN] +˙ ions was confirmed by the observation of metastable ions and the appearance energies of fragment ions. Interesting observations from these results were expulsion of an H atom in close proximity to the area around an OC group, a weak bonding interaction between sp 2 CH and an OC group, inducing specific hydrogen rearrangement, and characteristic charge localization on heteroatoms.