STEREOCHEMISTRY OF HOT HYDROGENS DISPLACEMENT AT sp$sup 3$ CARBON-HYDROGEN BONDS

Journal Article · Thu Jul 20 04:00:00 EDT 1961 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01475a003· OSTI ID:4843659

Henchman, M; Wolfgang, R

The stereochemistry of the displacement of hydrogen by hot hydrogen atoms has been studied at an sp/sup 3/ carbon atom in a gaseous molecule. The system used was the reaction of recoil tritium, from the nuclear reaction He/sub 3/(n,p)H/sub 3/, with optically active 2-butanol. There is 91 plus or minus 6% retention of configuration for displacement of the hydrogen atom directly bonded to the asymmetric carbon. For the displacement of all the hydrogens throughout the molecule, there is 94 plus or minus 3% retention of configuration. These results are well in accord with the model of hot hydrogen displacement postulating a fast, localized interaction occurring in about the characteristic pericd of a C --H bond vibration. According to such a model the short duration of the collision and the small size of the hydrogen atom allow no effective coupling mechanism for the concerted excitation of the several vibrational modes involved in the inversion process. (auth)

• Research Organization: Yale Univ., New Haven
• Sponsoring Organization: USDOE
• NSA Number: NSA-15-027659
• OSTI ID: 4843659
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 83; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ATOMS
BONDING
BUTANOL
CARBON
CHEMISTRY
COLLISIONS
DECOMPOSITION
EXCITATION
GASES
HELIUM
HYDROGEN
INTERACTIONS
MOLECULES
NUCLEAR REACTIONS
RECOILS
STEREOCHEMISTRY
TRITIUM
USES