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Stabilization of even‐electron ions by cyclization of substituents on 3 N ‐ and 4 N ‐nitrogens in 4 N ‐substituted cytosines
Author(s) -
Plaziak Adam S.,
Celewicz Lech,
Spychala Jaroslaw,
Golankiewicz Krzysztof
Publication year - 1988
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.1210230905
Subject(s) - substituent , fragmentation (computing) , chemistry , bicyclic molecule , ion , mass spectrum , electron ionization , nitrogen , medicinal chemistry , ionization , electron , organic chemistry , physics , computer science , operating system , quantum mechanics
Electron impact mass spectra of 4 N ‐substituted derivatives of cytosine are reported. The strong influence of 4 N ‐substituents on the mode of mass fragmentation occurring upon electron impact ionization was proved. The presence of α‐carbon in the 4 N ‐substituent extends the possibilities of fragmentation via rearrangement leading to formation of even‐electron bicyclic ions containing quaternary 3 N ‐nitrogen. When β‐carbon was present in the 4 N ‐substituent, the decomposition based on elimination of alkenes was detected as well as the rearrangement leading to formation of bicyclic even‐electron ions containing quaternary 3 N ‐ or 4 N ‐nitrogen.