Stereochemical investigations. XXXVII. Conformational characteristics of 4-cyanocyclohexanone and its methyl derivatives
The conformational equilibria in 4-cyanocyclohexanone and its 2- and 3-methyl derivatives were investigated by means of the averaged width of the signal for the methyl proton in the PMR spectra. The results from the measurements are compared with data calculated by molecular mechanics. It was found that the conformer with the axial cyano group has enhanced stability, and this was explained on the basis of long-range orbital interactions of the electronegative groups. In its conformational characteristics 4-cyanocyclohexanone is the most interesting representative of the 4-substituted cyclohexanones. The position of its conformational equilibrium is determined to a significant degree by long-range orbital interactions of the substituents and depends substantially on the polarity and specific characteristics of the solvent.
- Research Organization:
- M.V. Lomonosov Moscow State Univ. (USSR)
- OSTI ID:
- 5887359
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:11; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
AROMATICS
BENZENE
BOND ANGLE
CHEMICAL BONDS
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CONFIGURATION INTERACTION
CYCLOHEXANONE
DEUTERIUM COMPOUNDS
DIPOLES
DISTANCE
ELECTRONEGATIVITY
ELECTRONIC STRUCTURE
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN COMPOUNDS
INTERACTION RANGE
INTERACTIONS
IODINATED ALIPHATIC HYDROCARBONS
ISOMERS
ISOTOPE EFFECTS
KETONES
LINE WIDTHS
MATERIALS TESTING
MOLECULAR STRUCTURE
MULTIPOLES
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
PERTURBATION THEORY
SOLVENT PROPERTIES
SOLVENTS
SPECTRA
STEREOCHEMISTRY
TESTING