Deuterium isotope effects on the cyclobutyl-cyclopropylcarbinyl cation
Journal Article
·
· J. Am. Chem. Soc.; (United States)
Lithium aluminum deuteride reduction of cyclopropanecarboxylic acid produced ..cap alpha cap alpha..-dideuterated cyclopropylcarbinol which was converted to the cation. A peak assigned to nondeuterated methylenes was observed in the /sup 13/C NMR spectrum shifted upfield 1.77(-135/sup 0/C) and 1.24 ppM(-107/sup 0/C), indicating an equilibrium isotope effect. The upfield /sup 1/H NMR peak was also found to be shifted to higher field by 0.087(-130/sup 0/C) and 0.057 ppM (-80/sup 0/C). The downfield peak was unaffected. Apparently the equilibrium between nonequiv methylenes is perturbed by deuterium, but the chemical shift between the rapidly equilibrating hydrogens is very different between the two sets of nonequiv hydrogens. 1 figure.
- Research Organization:
- Yale Univ., New Haven, CT
- OSTI ID:
- 6572639
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 102; 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)
400303 -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKANES
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
CARBOXYLIC ACIDS
CATIONS
CHARGED PARTICLES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CYCLOALKANES
DEUTERIUM
DEUTERIUM COMPOUNDS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
IONS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLING
LIGHT NUCLEI
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
LOW TEMPERATURE
NMR SPECTRA
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
SPECTRA
STABLE ISOTOPES
TEMPERATURE DEPENDENCE
YIELDS
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
400303 -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKANES
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
CARBOXYLIC ACIDS
CATIONS
CHARGED PARTICLES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CYCLOALKANES
DEUTERIUM
DEUTERIUM COMPOUNDS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
IONS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLING
LIGHT NUCLEI
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
LOW TEMPERATURE
NMR SPECTRA
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
SPECTRA
STABLE ISOTOPES
TEMPERATURE DEPENDENCE
YIELDS