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Mass spectrometric study on 2‐amino‐ as ‐triazino[6,5‐ c ]quinoline and some of its derivatives
Author(s) -
Vékey K.,
Tamás J.,
Berényi E.,
Benkó P.
Publication year - 1985
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.1210200607
Subject(s) - chemistry , quinoline , substituent , intramolecular force , fragmentation (computing) , ion , electron ionization , medicinal chemistry , kinetic energy , leaving group , stereochemistry , organic chemistry , catalysis , operating system , physics , quantum mechanics , computer science , ionization
Electron impact induced fragmentations of 2‐amino‐ as ‐triazino[6,5‐ c ]quinoline and its 2‐methylamino, 2‐dimethylamino and 2‐benzylamino analogues have been investigated. The main primary decomposition route of both the singly and the doubly charged molecular ions is the N 2 loss. For the singly charged ions the critical energy of this reaction is 110±10 kJ mol −1 and the kinetic energy release is 61±4 kJ mol −1 . For the doubly charged ions these values are 90±10 kJ mol −1 and 5±2 kJ mol −1 , respectively, indicating a significantly different reaction profile. The further fragmentation of [MN 2 ] + ˙ ions consists of radical eliminations from the 2‐amino group with cleavages of the α‐ and β‐bonds. Here a significant substituent effect is eliminations found suggesting an intramolecular cyclization reaction with a substituent migration. D and 15 N labelling experiments have shown a minor extent of randomization of the labelled atoms and the occurrence of other hidden skeletal rearrangements during the fragmentation.