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General aspects of the mass spectra of some benzyloxyalkyl substituted purine and pyrimidine nucleoside analogues; A demonstration of the concept of charge localization
Author(s) -
Grose W. F. A.,
Eggelte T. A.,
Nibbering N. M. M.
Publication year - 1971
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.1210050708
Subject(s) - benzaldehyde , chemistry , molecule , pyrimidine , mass spectrum , ion , ether , purine , photochemistry , stereochemistry , organic chemistry , catalysis , enzyme
The molecular ions of the title compounds appear to lose a molecule of benzaldehyde or a benzyl radical. The first reaction is followed by the elimination of a second molecule of benzaldehyde, the second reaction by either the expulsion of a molecule of benzaldehyde or a molecule of benzylalcohol. These degradations can be readily explained by assuming charge localization in the purine or pyrimidine part of the molecular ions. For the successive loss of a benzyl radical and of a molecule of benzaldehyde from the molecular ions, however, charge localization at one of the ether oxygen atoms may also be responsible to some extent, as demonstrated by the mass spectrum of 1,3‐dibenzyloxy‐2‐ethylpropane.