Quantum-chemical investigation of monosubstituted cyclopropanes
Journal Article
·
· Theor. Exp. Chem. (Engl. Transl.); (United States)
OSTI ID:5895219
The applicability of the semiempirical MINDO/3 and MNDO methods is demonstrated for the determination of the relative changes in the strain of the three-carbon ring and examination of the contributions from the effects of substituents X to the stabilization energy of monosubstituted cyclopropanes (substituents H, OCH/sub 3/, NH/sub 2/, F, Cl, CH/sub 3/, CF/sub 3/, COCH/sub 3/, CN, NO/sub 2/). The best results, comparable with the data from nonempirical calculations, were obtained by the MINDO/3 method. The method correctly confers the changes in the geometry of substituted cyclopropane rings but systematically underestimates the strain energy by 20-40 kJ/mole. To judge from the ..delta..E/sub strain/ values, the ..pi..-accepting effect of the substituents NO/sub 2/, COCH/sub 3/, and CN plays a major role in determining the electronic structure, suppressing the destabilizing sigma-acceptor effect. In the case of the substituents F, Cl, OCH/sub 3/, and NH/sub 2/ the stabilizing ..pi..-donor effect is either completely suppressed or is partly balanced by the sigma-acceptor effect.
- Research Organization:
- State Institute of Applied Chemistry, Leningrad, USSR
- OSTI ID:
- 5895219
- Journal Information:
- Theor. Exp. Chem. (Engl. Transl.); (United States), Journal Name: Theor. Exp. Chem. (Engl. Transl.); (United States) Vol. 21:4; ISSN TEXCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
640302* -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKANES
ATOMIC MODELS
BINDING ENERGY
C CODES
CHARGE DISTRIBUTION
CHEMICAL BONDS
CHEMICAL REACTIONS
COMPUTER CODES
COMPUTERIZED SIMULATION
CONFORMATIONAL CHANGES
CYCLOALKANES
ELECTRON DENSITY
ELECTRON TRANSFER
ELECTRONIC STRUCTURE
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
FERMIONS
HYDROCARBONS
INTERATOMIC FORCES
ISOMERIZATION
LEPTONS
M CODES
MATHEMATICAL MODELS
MECHANICS
MOLECULAR MODELS
ORGANIC COMPOUNDS
POTENTIAL ENERGY
PROPANE
QUANTUM MECHANICS
S CODES
SIMULATION
STRAINS
VALENCE
400201 -- Chemical & Physicochemical Properties
640302* -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKANES
ATOMIC MODELS
BINDING ENERGY
C CODES
CHARGE DISTRIBUTION
CHEMICAL BONDS
CHEMICAL REACTIONS
COMPUTER CODES
COMPUTERIZED SIMULATION
CONFORMATIONAL CHANGES
CYCLOALKANES
ELECTRON DENSITY
ELECTRON TRANSFER
ELECTRONIC STRUCTURE
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
FERMIONS
HYDROCARBONS
INTERATOMIC FORCES
ISOMERIZATION
LEPTONS
M CODES
MATHEMATICAL MODELS
MECHANICS
MOLECULAR MODELS
ORGANIC COMPOUNDS
POTENTIAL ENERGY
PROPANE
QUANTUM MECHANICS
S CODES
SIMULATION
STRAINS
VALENCE