Intramolecular hydrogen bonding as reflected in the deuterium isotope effects on carbon-13 chemical shifts. Correlation with hydrogen bond energies
Journal Article
·
· J. Am. Chem. Soc.; (United States)
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.
- Research Organization:
- Hercules Inc., Wilmington, DE
- OSTI ID:
- 5333839
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 108:8; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
ADDUCTS
ALDEHYDES
AROMATICS
BINDING ENERGY
CARBON 13
CARBON ISOTOPES
CHEMICAL BONDS
CHEMICAL SHIFT
DATA
DEUTERIUM
DEUTERIUM COMPOUNDS
ELEMENTS
ENERGY
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
HYDROGEN
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFORMATION
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
MOLECULAR STRUCTURE
NONMETALS
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHENOLS
QUINONES
STABLE ISOTOPES
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
ADDUCTS
ALDEHYDES
AROMATICS
BINDING ENERGY
CARBON 13
CARBON ISOTOPES
CHEMICAL BONDS
CHEMICAL SHIFT
DATA
DEUTERIUM
DEUTERIUM COMPOUNDS
ELEMENTS
ENERGY
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
HYDROGEN
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFORMATION
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
MOLECULAR STRUCTURE
NONMETALS
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHENOLS
QUINONES
STABLE ISOTOPES