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Sulfonylation of phenols in the presence of pyridine bases (in Russian)

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6388574
; ; ;

The sulfonylation of phenols by aromatic sulfonyl chlorides in the presence of pyridine bases in nitrobenzene was studied by potentiometric titration. A linear dependence was found between the logarithms of the catalytic constants and the sigma-Hammett constants of the substituents in sulfonyl chloride (rho = 1.06). The contribution of the inductive (rho/sup 0/ = 0.39) and resonance (rho/sub R//sup +/ = -0.45) effects of the substituents in phenol to the reaction kinetics of the process was evaluated by means of a two-parametric equation. The deuterium kinetic isotopic effect (k/sub N//sup D//d/sub N//sup H/ = 1) was studied. It was concluded that the mechanism of the catalysis is nucleophilic with generally basic assistance from the side of a free base.

Research Organization:
Donetsk Polytechnic Institute, USSR
OSTI ID:
6388574
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:7; ISSN JOCYA
Country of Publication:
United States
Language:
Russian

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
ACTIVATION ENERGY
AROMATICS
AZINES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
DEUTERATION
DEUTERIUM
DEUTERIUM COMPOUNDS
ENERGY
EQUATIONS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
HYDROXY COMPOUNDS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
KINETIC EQUATIONS
KINETICS
LIGHT NUCLEI
MELTING POINTS
NITRO COMPOUNDS
NITROBENZENE
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHENOLS
PHYSICAL PROPERTIES
POTENTIOMETRY
PYRIDINES
REACTION KINETICS
STABLE ISOTOPES
SULFONATION
SULFONES
THERMODYNAMIC PROPERTIES
TITRATION
TRANSITION TEMPERATURE