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17 O NMR spectroscopic study of substituted 9‐fluorenones
Author(s) -
Boykin D. W.,
NowakWydra Barbara
Publication year - 1991
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260290211
Subject(s) - chemistry , intramolecular force , chemical shift , substituent , fluorenone , acetonitrile , aromaticity , proton nmr , carbon 13 nmr , stereochemistry , computational chemistry , molecule , organic chemistry , fluorene , polymer
The 17 O NMR chemical shift data for 23 9‐fluorenones in acetonitrile at 75°C are reported. 17 O NMR data for the 3‐substituted 9‐fluorenones are correlated with 17 O NMR data for 4‐substituted acetophenones. Chemical shift data for 1‐halogeno‐9‐fluorenones are deshielded relative to the 3‐isomers, suggesting important repulsive van der Waals interactions. The keto carbonyl signal for 9‐fluorenone‐1‐carboxylic acid is substantially shielded, as expected, from intramolecular hydrogen bonding. The data for several multi‐substituted 9‐fluorenones demonstrate that substituent effects are additive for the 9‐fluorenones.