Quantum-chemical investigation of the 1,2-proton shift in protonated five-membered aromatic heterocycles

Journal Article · Thu Feb 28 23:00:00 EST 1985 · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)

OSTI ID:6771737

Abronin, I A; Gorb, L G; Litvinov, V P

Calculations of the energetics of the 1,2-proton shift in protonated five-membered aromatic heterocycles - pyrrole, furan, and thiophene - have been carried out by the SCF MO LCAO method in the MINDO/3 approximation and nonempirically on the OST-3GF (OST-3GF) basis. The general features of this process, and also the influence of solvation and of taking into account the vacant d-AOs of the sulfur atom in the protonated form of thiophene on the results of the calculation are considered. The results obtained have been used for a discussion of the activity and selectivity of the heterocycles considered in aromatic electrophilic substitution reactions.

• Research Organization: N.D. Zelinskii Institute of Organic Chemistry, Acad. of Sci., Moscow
• OSTI ID: 6771737
• Journal Information: Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 20:9; ISSN CHCCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400101 -- Activation
Nuclear Reaction
Radiometric & Radiochemical Procedures
400201* -- Chemical & Physicochemical Properties
ACTIVATION ANALYSIS
ACTIVATION ENERGY
AROMATICS
AZOLES
BARYON REACTIONS
BENZENE
CHARGED-PARTICLE REACTIONS
CHEMICAL ANALYSIS
CHEMICAL PROPERTIES
COMPUTERIZED SIMULATION
DIAGRAMS
ELEMENTS
ENERGY
FURANS
HADRON REACTIONS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
IONIZATION POTENTIAL
IRRADIATION
LCAO METHOD
MECHANICS
NONMETALS
NUCLEAR REACTIONS
NUCLEON REACTIONS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PROTON REACTIONS
PYRROLES
QUANTITATIVE CHEMICAL ANALYSIS
QUANTUM MECHANICS
SIMULATION
SOLVATION
SULFUR
THIOPHENE