Some features of the aminolysis of benzoyl chloride catalyzed by 4-dimethylaminopyridine in low-polarity aprotic media
The reaction of p-nitroaniline with benzoyl chloride in the presence of 4-dimethylaminopyridine leads to the formation of benzoyl-4-dimethylaminopyridinium chloride. The reactivity of this intermediate and the mechanism of the nucleophilic effect of the pyridinium base are due to the nature of the complexation in the intermediate. From the kinetic data and from the results of a study of the electric conductivity of benzoyl chloride-4-dimethylaminopyridine mixtures with various compositions it was concluded that dimers and larger homoassociates are formed, in addition to the hydrogen-bonded associates of the arylamine with the salt. The results demonstrate the presence of a multitude of associated forms in the intermediate product of nucleophilic catalysis in methylene chloride and other low-polarity aprotic media.
- OSTI ID:
- 5949528
- 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
ACETONITRILE
AMINES
AMMONIUM CHLORIDES
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
AZINES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHLORIDES
CHLORINE COMPOUNDS
ELECTRIC CONDUCTIVITY
ELECTRICAL PROPERTIES
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
KINETICS
METHYLENE CHLORIDE
MOLECULAR STRUCTURE
NITRILES
NITRO COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
PHYSICAL PROPERTIES
PYRIDINES
PYRIDINIUM COMPOUNDS
QUATERNARY COMPOUNDS
REACTION KINETICS
SOLVENTS