Anomalous hydrogen-deuterium exchange of cyclic. beta. -keto sulfides
Journal Article
·
· J. Org. Chem.; (United States)
The protons at carbon-4 display a higher kinetic acidity than those at carbon-2 in thiolanone when the hydrogen deuterium exchange is catalyzed by pyridine. The purpose of this study was to measure and compare the rates of hydrogen-deuterium exchange of thiolanone and three other ketones 3-pentanone, cyclopentanone, and 1-(methylthio)-2-propanone. Results are reported using 3-pentanone as a standard. They demonstrate that the kinetic acidity of C-H bonds at carbon 4 of thiolanone is approx. 1000 to 5000 times higher than those at carbon 2 and carbon 4 of 3-pentanone.
- Research Organization:
- American Univ., Washington, DC
- OSTI ID:
- 7094151
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:13; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Journal Article
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Mon Dec 19 23:00:00 EST 1960
· Journal of the American Chemical Society (U.S.)
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OSTI ID:4118758
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Tue Aug 26 00:00:00 EDT 1958
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· J. Am. Chem. Soc.; (United States)
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OSTI ID:7326311
Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALCOHOLS
AZINES
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
COMPARATIVE EVALUATIONS
DATA
DEUTERIUM
ENOLS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFORMATION
ISOTOPES
ISOTOPIC EXCHANGE
KETONES
KINETICS
LABELLING
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PH VALUE
PYRIDINE
PYRIDINES
REACTION KINETICS
RESONANCE
STABLE ISOTOPES
THIOLS
TIME DEPENDENCE
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALCOHOLS
AZINES
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
COMPARATIVE EVALUATIONS
DATA
DEUTERIUM
ENOLS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFORMATION
ISOTOPES
ISOTOPIC EXCHANGE
KETONES
KINETICS
LABELLING
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PH VALUE
PYRIDINE
PYRIDINES
REACTION KINETICS
RESONANCE
STABLE ISOTOPES
THIOLS
TIME DEPENDENCE