Dependence of substituent electronic effects in /pi/-systems on the nature of molecular orbitals. XIII. Substituent effects in benzene radical-cations and radical-anions and analysis of the electrochemical reduction potentials of substituted benzenes

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

OSTI ID:6008007

Koptyug, V A; Starichenko, V F; Breslav, I I

The contribution of substituent orbitals to the highest occupied and lowest unoccupied /pi/-orbitals of substituted benzenes was evaluated in the framework of the simple LCFO method using previously proposed parametrization. The values obtained correlate satisfactorily with the a/sub N/ coupling constants in the ESR spectra of the radical-cations of substituted N,N-dimethylanilines and radical-anions of substituted nitrobenzenes and benzonitriles. The calculations of the energies of the lowest unoccupied /pi/-orbitals of substituted nitrobenzenes and benzonitriles permits estimation of the electrochemical reduction potentials of these compounds.

• Research Organization: Novosibirsk Institute for Organic Chemistry (USSR)
• OSTI ID: 6008007
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:1; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
656002 -- Condensed Matter Physics-- General Techniques in Condensed Matter-- (1987-)
75 CONDENSED MATTER PHYSICS
SUPERCONDUCTIVITY AND SUPERFLUIDITY
AMINES
ANGULAR MOMENTUM
ANIONS
AROMATICS
ATOMIC MODELS
BENZENE
BINDING ENERGY
CATIONS
CHARGED PARTICLES
CHEMISTRY
CONFIGURATION INTERACTION
CORRELATIONS
COUPLING
COUPLING CONSTANTS
ELECTROCHEMISTRY
ELECTRON CORRELATION
ELECTRON SPIN RESONANCE
ELECTRONIC STRUCTURE
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
FERMIONS
HYDROCARBONS
INTERMEDIATE COUPLING
IONIZATION POTENTIAL
IONS
ISOTOPES
J-J COUPLING
LEPTONS
LIGHT NUCLEI
MAGNETIC RESONANCE
MATHEMATICAL MODELS
MOLECULAR STRUCTURE
NITRILES
NITRO COMPOUNDS
NITROBENZENE
NITROGEN 14
NITROGEN ISOTOPES
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PARTICLE PROPERTIES
RADICALS
REDOX POTENTIAL
RESONANCE
SPIN
STABLE ISOTOPES
VALENCE