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Paramagnetic products formed in the reactions of organometallic compounds. XII ESR study of oxido anion substituted diaryl ketyl radicals
Author(s) -
Malik Ľ.,
Staško A.,
Mat'ašová E.,
Tkáč A.
Publication year - 1981
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270150117
Subject(s) - ketyl , chemistry , radical , medicinal chemistry , alkyl , ring (chemistry) , reagent , paramagnetism , ion , organic chemistry , physics , quantum mechanics
Abstract In the reactions of alkyl‐substituted‐benzenecarboxylic and ‐2‐hydroxybenzenecarboxylic acids (ArCOOH) with alkyl‐substituted phenyl Grignard reagents (RMgX) in the presence of nickel, ketyl radicals ArCO − R are formed. The para substituents (H, Me, Et, Isopr and t ‐Bu) of R increase the non‐equivalence of its ortho protons (a change of a 2 H = 0.43 mT, a 6 H = 0.422 mT to 0.435 mT, 0.395mT respectively, on substituting t ‐butyl for H at position 4). The oxido anion group originating from 2‐hydroxybenzenecarboxylic acid has a strong push effect and nearly doubles the unpaired spin density on the phenyl ring R.