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Alkanesulfonylation reactions. XII. Effect of the nature of the solvent on the rate and mechanism of the propanesulfonylation of phenol in the presence of dimethylbenzylamine

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:7076311
; ;

The kinetics of the reaction of propanesulfonyl chloride with phenol in the presence of dimethylbenzylamine in p- and m-xylene, toluene, chloroform, chlorobenzene, methylene chloride, and nitrobenzene at 30/sup 8/C were studied by GLC and potentiometric titration. The degree of reaction by the sulfane mechanisms increases with increase in the polarity of the medium, and the contribution from the mechanism of general base catalysis decreases. The effect of the solvent polarity on the reaction rate is described by the Kirkwood equation. Structures are proposed for the transition states of the concurrent reaction mechanisms.

Research Organization:
Institute of Physical Organic Chemistry and Coal Chemistry, Donetsk (USSR)
OSTI ID:
7076311
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:4; ISSN JOCYA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKYLATED AROMATICS
ALKYLATION
AMINES
AROMATICS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINATED AROMATIC HYDROCARBONS
CHLOROFORM
COMPARATIVE EVALUATIONS
ENERGY
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HYDROCARBONS
HYDROXY COMPOUNDS
KINETICS
METHYLENE CHLORIDE
NITRO COMPOUNDS
NITROBENZENE
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
ORGANIC SULFUR COMPOUNDS
PHENOLS
REACTION KINETICS
SOLVENT PROPERTIES
SOLVENTS
SULFONATION
TOLUENE
XYLENES