Carbon-13 nuclear magnetic resonance studies of aromatic compounds: comparison of hydrogen bonding effects in phenols, anilides, and anilines
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1058-1063
- https://doi.org/10.1039/p29790001058
Abstract
Two- and three-bond 13C n.m.r. coupling constants to 1H are reported for ring-substituted phenols, anilides, and anilines, plus limited data for thiophenols. The magnitude of the three-bond coupling constants to the phenolic hydroxy were rather insensitive to structural variations designed to alter the geometry of the coupled nuclei and raises the question of the exact geometric dependence of 3J on geometry. For acetanilides, the difference in magnitude between 3Janti and 3Jsyn is small. For anilines, the data are not suggestive of a geometric relationship. Thiophenols are similar to phenols. The influence of substitution on coupling constants between ring carbons and hydrogens is discussed briefly. Chemical shifts are reported for 16-ortho-substituted aromatic compounds.Keywords
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