The Effect of Intramolecular Hydrogen Bonding on the Rotational Barriers about the C–N Bonds of o-Hydroxyarenecarboxamides
- 1 November 1987
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (11) , 3973-3978
- https://doi.org/10.1246/bcsj.60.3973
Abstract
Rotational barriers about the C–N bonds of several o-hydroxyarenecarboxamides were determined in four solvents (namely, chloroform, pyridine, methanol, and dimethyl sulfoxide) by DNMR spectroscopy and compared with those of arenecarboxamides void of ortho-hydroxyl group. The height of the rotational barrier is correlated with the strength of the intramolecular O–H···O=C hydrogen bond. The unusual solvent effect on the rotational barriers of these hydroxy–amides are ascribed to the cleavage of the intramolecularly hydrogen bonded chelate ring which occurs in both hydrogen-donating and -accepting solvents.Keywords
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