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The mass spectrometry of DT‐and monosubstituted biphenyls: Dependence of fragmentation patterns on position of substitution
Author(s) -
Sheley Curtis F.,
Patterson Robert T.
Publication year - 1974
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.1210090802
Subject(s) - biphenyl , fragmentation (computing) , chemistry , hydroxymethyl , fluorene , polyatomic ion , ion , mass spectrometry , medicinal chemistry , methanol , computational chemistry , stereochemistry , organic chemistry , chromatography , polymer , computer science , operating system
This paper describes the mass spectroscopy of a series of biphenyl derivatives substituted in the 2,2′, 4,4′ and 2 positions. The substitutent functional groups are carbomethoxy, carbothoxy, carboxylic acid and hydroxymethyl. In addition, some results are reported on the spectroscopy of the d 5 ‐carboethoxy derivatives, the 2‐ and 2,2′‐α d 2 ‐ hydroxymethyl derivatives and fluorene‐4‐methanol. The molecular ions of the 4,4′‐disubstituted biphenyl derivatives are far more stable than those of the 2,2′ isomers. It is also observed that the fragmentation patterns of these two sets of isomers are sharply different. Paradoxically, the 2‐substituted biphenyl derivatives give relatively stable molecular ions and their fragmentation patterns are frequently different from those of the corresponding 2,2′‐disubstituted biphenyls. The bulk of the evidence presented in this paper suggests that the usual sort of ‘ ortho effect’ is not a significant factor in the fragmentation mechanisms proposed for the 2,2′‐disubstituted biphenyl derivatives.