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Stabilization of even‐electron ions in 4‐amino‐substituted cytosines. Appearance of the strong ortho effect between an aryl substituent and the pyrimidinyl ring
Author(s) -
Plaziak Adam S.,
Spychala Jaroslaw,
Golankiewicz Krzysztof
Publication year - 1989
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.1210241203
Subject(s) - substituent , moiety , fragmentation (computing) , aryl , chemistry , ion , methylene , ring (chemistry) , medicinal chemistry , stereochemistry , cytosine , organic chemistry , dna , biochemistry , alkyl , computer science , operating system
The mass fragmentation of 4‐arylaminocytosine derivatives was investigated and it was found that the ortho effect is mainly responsible for the strong stabilization of even‐electron ions formed during fragmentation. The ortho effect in this class of compounds completely eliminates other possible fragmentation patterns. This effect disappears when the aryl substituent is separated from the 4‐amino group of the cytosine moiety by a methylene group.