Measurement of deuterium kinetic isotope effects in organic reactions by natural-abundance deuterium NMR spectroscopy

Journal Article · Wed Sep 05 00:00:00 EDT 1984 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00330a071· OSTI ID:6199771

Pascal, Jr, R A; Baum, M W; Wagner, C K; Rodgers, L R

The usefulness of /sup 2/H NMR spectroscopy for measuring natural-abundance deuterium isotope effects is demonstrated. The spectrum of dimethly 2-cyclohexylmalonate prepared by the photolysis of dimethyldiazomalonate in excess cyclohexane illustrates that isotope effects can be measured easily because the H from the ruptured CH bond is retained in the product (results are compared with those of an experiment using 1:1 cyclohexane:cyclohexane-d/sub 12/ as solvent). In the instance of reactions in which CH cleavage results in loss of H to the solvent, the amount of transferred hydrogen must be obtained indirectly. An example of such a reaction is included.

• Research Organization: Princeton Univ., NJ
• OSTI ID: 6199771
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 106:18; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
ALKANES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CYCLOALKANES
CYCLOHEXANE
DATA
DATA ANALYSIS
DECOMPOSITION
DEUTERIUM
DIAZO COMPOUNDS
DICARBOXYLIC ACIDS
DIMERS
ESTERS
EXPERIMENTAL DATA
HYDROCARBONS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
MALONIC ACID
NMR SPECTRA
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
PHOTOCHEMICAL REACTIONS
PHOTOLYSIS
SOLVENTS
SPECTRA
STABLE ISOTOPES