Abstract
The carbon-13 resonances of atoms bearing phenolic or enolic hydroxyl groups, that are engaged in intramolecular hydrogen bonds, experience large (/sup 2/..delta.. may exceed 1 ppm) upfield deuterium isotope effects. The magnitude of the two-bond isotope effect, /sup 2/..delta.., correlates with the hydrogen bond energy as obtained from the hydroxyl proton chemical shift. In the conjugated systems investigated in this work, the isotope effects extend over several (up to six) chemical bonds. The signs and magnitudes of the long-range isotope effects are related to molecular structure.
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