Catalytic sulfonylation of phenol by sterically hindered sulfonyl chlorides

Journal Article · Wed Apr 20 04:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5949533

Vizgert, R V; Maksimenko, N N; Rubleva, L I

The sulfonylation of phenol by substituted arenesulfonyl chlorides XArSo/sub 2/Cl (X = 2-CH/sub 3/, 2-C/sub 2/H/sub 5/, 4-t-C/sub 4/H/sub 9/, 2,4,6-(C/sub 2/H/sub 5/)/sub 3/, 2,4,6-(i-C/sub 3/H/sub 7/)/sub 3/) in the presence of diethylamine in benzene was studied by potentiometric titration. A linear relation was obtained between the logarithms of the catalytic rate constants and the steric constants E/sub s//sup 0/ of the substituents in the sulfonyl chloride. The contribution from the induction and steric effects of the substituents at position 2 to the kinetics of the process was assessed. It was concluded that the steric effects plays a predominant role over the induction and resonance effects.

• Research Organization: Donetsk Polytechnic Institute (USSR)
• OSTI ID: 5949533
• 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

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
AMINES
AROMATICS
BENZENE
BINDING ENERGY
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
EQUATIONS
ESTERS
FERMIONS
HYDROCARBONS
HYDROXY COMPOUNDS
INHIBITION
KINETIC EQUATIONS
KINETICS
LEPTONS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SOLVENTS
ORGANIC SULFUR COMPOUNDS
PHENOL
PHENOLS
POTENTIOMETRY
REACTION KINETICS
RESONANCE
SOLVENTS
STEREOCHEMISTRY
SULFONIC ACID ESTERS
SYNTHESIS
TITRATION
VALENCE
YIELDS