THE REACTIONS OF RECOIL TRITIUM ATOMS WITH UNSATURATED ACIDS

Journal Article · Thu Oct 20 00:00:00 EDT 1960 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01505a019· OSTI ID:4117517

White, R M; Rowland, F S

Recoil H/sup 3/ atoms substitute into all of the hydrogen positions of crystalline cis- and trans-cinnamic acid and of sodium trans-cinnamate. The specific activities of the different positions of the aromatic ring are within 25% of each other for the trans compounds (and benzoic acid), and decrease in the order ortho> para> meta. The specific activity of the o-position in cis-cinnamic acid is about half that of the m- and p-positions, perhaps because of steric interference by the -- COOH group. Replacement of nonlabile hydrogen by recoil H/ sup 3/ in maleic and fumaric acids is accompanied by geometric cis--trans isomerization in <5% of the substitutions. Addition to the double bond to form succinic acid is about half as frequent as substitution for hydrogen in the parent molecule. Addition to the triple bond of phenylpropiolic acid leads to labeled cinamic acid, more than 90% in the trans form. The substitution of H/sup 3/ for hydrogen is explained in terms of high kinetic energy reactions involving a minimum of atomic motion during substitution. (auth)

• Research Organization: Univ. of Kansas, Lawrence
• Sponsoring Organization: USDOE
• NSA Number: NSA-15-002654
• OSTI ID: 4117517
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 82; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ACIDS
ACRYLIC ACID
ALKANES
ATOMS
BENZOIC ACID
CHEMISTRY
CINNAMIC ACID
HYDROGEN
ISOMERS
ISOTOPIC EXCHANGE
MOTION
ORGANIC COMPOUNDS
PHENYL RADICALS
RECOILS
SODIUM COMPOUNDS
TRITIUM