CARBON-14 KINETIC ISOTOPE EFFECTS IN NUCLEOPHILIC SUBSTITUTION REACTIONS

Journal Article · Thu Oct 31 23:00:00 EST 1957 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01578a017· OSTI ID:4346252

Bender, M L; Hoeg, D F

The C/sup 14/ kinetic isotope effects in the nucleophilic substitution reactions of methyl iodide-C/sup 14/ with triethylamine, pyridine, hydroxide ion and silver ion have been investigated. The kinetic isotope effects (k/sub 12/k/ sub 14/) found in these reactions were l.l0, l.14, 1.09 and 1.09, respectively. The surprisingly large kinetic isotope effects in these S/sub N/2 reactions are of the same magnitude as many effects noted in reactions proceeding only with bond rupture. A comparison has been made between the observed kinetic isotope effects and those calculated using an equation of Bigeleisen and Wolfsberg for three-center reactions. It appears that the magnitude of the kinetic isotope effect is of only limited use in differentiating between two-center and three- center reactions in nucleophilic substitution (SNl and S/sub N/2 reactions). (auth)

• Research Organization: Illinois Inst. of Tech., Chicago
• Sponsoring Organization: USDOE
• NSA Number: NSA-12-002227
• OSTI ID: 4346252
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 79; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ALLOTROPY
AMINES
ANISOTROPY
CARBON 14
CHEMICAL REACTIONS
CHEMISTRY
COPPER
DEFORMATION
EQUATIONS
ETHYL RADICALS
HARDENING
HYDROXIDES
IRON
ISOTOPE EFFECTS
LATTICES
MARTENSITE
MATHEMATICS
MEASURED VALUES
METALLOGRAPHY
METHYL RADICALS
ORGANIC IODINE COMPOUNDS
PRESSURE
PYRIDINES
SHOCK WAVES
SILVER
THICKNESS
VELOCITY