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The effect of para ‐substitution on the mass spectra of arylsulphonate esters of neopentanol
Author(s) -
Mamer Orval A.,
Padmapriya Abeysinghe A.,
Just George
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.1210201210
Subject(s) - chemistry , substituent , mass spectrum , polyatomic ion , aryl , fragmentation (computing) , medicinal chemistry , alkyl , ion , hydrogen atom , dibenzofuran , benzoates , organic chemistry , computer science , operating system
The mass spectra of several para ‐substituted benzenesulfonic and benzoic esters of unlabelled and 1,1‐ d 2 ‐neopentyl alcohol are examined and compared. Evidence is presented of migration of the aryl group from the sulfur to an oxygen atom in the molecular ions of the sulfonic esters. The nature of the fragmentation processes and the occurrence of metastable ions for these processes are both much more dependent upon the polarity of the para substituent in the case of the sulfonates than for the benzoates. Elimination of C 5 H 10 occurs from the molecular ion of the p ‐methoxysulfonate with transfer to the residual ion of a hydrogen atom selected randomly from the alkyl fragment, while in the case of the p ‐aminosulfonate, incomplete randomization is demonstrated.