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The ortho effect in the mass spectra of ortho/para isomers of bisphenol a derivatives and related compounds
Author(s) -
Pleshkova Alexandra P.,
Uspenskaya Mari.,
Volkovitch Sergei V.
Publication year - 1994
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.1210290105
Subject(s) - chemistry , mass spectrum , deuterium , isopropyl , bisphenol a , medicinal chemistry , ion , ring (chemistry) , silylation , spectral line , hydrogen , bisphenol , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics , astronomy , epoxy
Abstract New examples of the ortho effect in bisphenol A derivatives including interaction of the hydrogen of the ortho ‐hydroxy group with the neighbouring aromatic ring have been observed. The characteristic ions [M PhOH] +middot; ( m/z = 134) and [M CH 3 PhOH] + ( m/z = 119) were shown to form through the hydrogen transfer from hydroxy and isopropyl groups, respectively. The spectra of cyclic derivatives having ortho ‐hydroxy functions show [M 43] + , [M C 8 H 9 O] + , m/z = 147, m/z = 135 and [M C 9 H 10 O] + ions. The proposed mechanims of the corresponding transformations were supported by mass spectra of deuterated analogues, methyl and trimethyl silyl ethers.