Kinetics of the reaction of adamantane and its derivatives with nitric acid

Journal Article · Wed Aug 10 00:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887584

Klimochkin, Yu N; Moiseev, I K

The reaction of adamantane compounds with nitric acid in methylene chloride is of first order with respect to the substrate, and its rate is proportional to the fifth power of the nitric acid concentration. A considerable kinetic isotope effect was found (4.4 /plus minus/ 0.3). The rate constants are linearly related to the solvolysis rate constants of the corresponding bromine derivatives and the Taft induction constants. A possible mechanism for oxynitration, including the removal of a hydride ion as controlling stage is proposed.

• Research Organization: V.V. Kuibyshev Kuibyshevsk Polytechnical Institute (USSR)
• OSTI ID: 5887584
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:3; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
ACTIVATION ENERGY
ADAMANTANE
ALKALI METAL COMPOUNDS
ALKANES
ARRHENIUS EQUATION
CARBOXYLIC ACID ESTERS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CYCLOALKANES
DECOMPOSITION
DEHYDRIDATION
ELECTRONEGATIVITY
ENERGY
EQUATIONS
ESTERS
HYDROCARBONS
HYDROGEN COMPOUNDS
INORGANIC ACIDS
ISOTOPE EFFECTS
KINETICS
METHYLENE CHLORIDE
NITRATES
NITRATION
NITRIC ACID
NITROGEN COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
POTASSIUM COMPOUNDS
POTASSIUM NITRATES
REACTION KINETICS
SEPARATION PROCESSES
SOLVOLYSIS