Acid deuterium exchange in methoxyquinolines and their N-oxides (in Russian)
Kinetic studies of acid deuterium exchange have been carried out for a series of isomeric 6-, 7-, 8-methoxyquinolines and their N-oxides, in comparison with the analogous carbocyclic compounds. It has been found that methoxyquinolines are deuterated in the N-protonated form, whereas the N-oxides are reactive in their neutral forms. In full agreement with data for the reactivity of these heterocycles in nitration, quantum chemical calculations show that in exchange in 6-methoxyquinoline and its N-oxide the preferred site for electrophilic attack is the 5-position, and in the 7-isomers the 8-position is preferred. The rate is lower in the 8-isomer, owing to the presence in the latter of intramolecular hydrogen bonding. The probable structure of the transition state in the reaction is discussed.
- Research Organization:
- State Institute of Applied Chemistry, Leningrad, USSR
- OSTI ID:
- 6423742
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 22:5; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- Russian
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74 ATOMIC AND MOLECULAR PHYSICS
ACTIVATION ENERGY
AROMATICS
ATOMIC MODELS
AZAARENES
AZINES
BINDING ENERGY
CHALCOGENIDES
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DEUTERATION
DEUTERIUM
DEUTERIUM COMPOUNDS
ELECTRON DENSITY
ELECTRONIC STRUCTURE
ELEMENTS
ENERGY
HEAVY WATER
HETEROCYCLIC COMPOUNDS
HYDROGEN
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LIGHT NUCLEI
MASS SPECTRA
MATHEMATICAL MODELS
MECHANICS
MOLECULAR ORBITAL METHOD
NONMETALS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
OXIDES
OXYGEN COMPOUNDS
PYRIDINES
QUANTUM MECHANICS
QUINOLINES
REACTION KINETICS
SOLVENTS
SPECTRA
STABLE ISOTOPES
VALENCE
WATER