Evidence on internal return from isotope effects in the hydrogen--deuterium exchange of benzyl sulfoxides. A caveat re interpretation of isotopic exchange rates. [Benzyl methyl sulfoxide and the bridged biaryl sulfoxide]
Journal Article
·
· J. Am. Chem. Soc.; (United States)
Measurements were made of the primary isotope effects k/sub H//k/sub T/ and k/sub D//k/sub T/ in the isotopic exchange of each diastereotopic proton of benzyl methyl sulfoxide and of two of the benzylic protons of the bridged biaryl sulfoxide. NMR, low voltage mass spectroscopy and tritium assays were used to determine the isotope content and the proportions of the diastereomers. Evidence of internal return was observed for the exchange reaction for the biaryl sulfoxide in tert-butyl alcohol-O-d. (DDA)
- Research Organization:
- Univ. of Ottawa
- OSTI ID:
- 7267344
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 98:14; 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)
AROMATICS
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
CHEMICAL REACTION KINETICS
DEUTERIUM
HYDROGEN ISOTOPES
INTERMEDIATE STRUCTURE
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LIGHT NUCLEI
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RADIOISOTOPES
REACTION KINETICS
STABLE ISOTOPES
STEREOCHEMISTRY
SULFOXIDES
TRITIUM
YEARS LIVING RADIOISOTOPES
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
400303 -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
AROMATICS
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
CHEMICAL REACTION KINETICS
DEUTERIUM
HYDROGEN ISOTOPES
INTERMEDIATE STRUCTURE
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LIGHT NUCLEI
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RADIOISOTOPES
REACTION KINETICS
STABLE ISOTOPES
STEREOCHEMISTRY
SULFOXIDES
TRITIUM
YEARS LIVING RADIOISOTOPES