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The mass spectral fragmentation of 2‐aryl‐N, N′‐dimethyl‐1,3‐imidazolidines and 2‐aryl‐1‐3‐dioxolanes
Author(s) -
Horodniak J. W.,
Wright J.,
Indictor N.
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.1210051106
Subject(s) - carbonium ion , aryl , fragmentation (computing) , chemistry , substituent , electron ionization , ion , stereochemistry , medicinal chemistry , organic chemistry , alkyl , computer science , ionization , operating system
2‐Aryl‐N,N'‐dimethyl‐1,3‐imidazolidines and 2‐aryl‐1,3‐dioxolanes were subjected to 70 eV spectral analysis. Fragmentation pathways for both series of compounds are suggested. Aryl vs. benzylic hydrogen fragmentations were subjected to Hammett σ + ρ plots. Incipient charge on the benzyl carbonium ion was stabilized by electron donating groups in both series of compounds. Dioxolanes were more sensitive to substituent effects (ρ = −0.639) than the imidazolidines (ρ = −0.251) implying that the positive charge on the fragmenting ion is more localized at the benzylic position of the imidazolidines than of the dioxolanes.