Desulfonation of aromatic sulfonic acids in acidic media: the kinetic isotope effect

Journal Article · Sat Dec 19 23:00:00 EST 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6364408

Krylov, E N; Kol'tsova, M V

The acid-catalyzed substitution of the sulfo group in mesitylene- and p-toluene-sulfonic acids by hydrogen (deuterium), which takes place in sulfuric, deutero-sulfuric, and phosphoric acids at various temperatures and acidities, was investigated. It was found that the solvent-reagent (D/sub 2/O-D/sub 2/SO/sub 4/) has a primary kinetic isotope effect during the desulfurization of mesitylenesulfonic acid (k/sub H//k/sub D/ = 2.8 + 0.3), and this indicate that the reaction rate is controlled by proton (deuteron) transfer. The high value of the Broensted coefficient (..cap alpha.. = 0.88 +/- 0.04) indicates that the structure of the transition state is close to a sigma complex.

• Research Organization: Ivanovo State Univ. (USSR)
• OSTI ID: 6364408
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:7; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALKYLATED AROMATICS
AROMATICS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DECOMPOSITION
DESULFURIZATION
DEUTERIUM
DEUTERIUM COMPOUNDS
ELEMENTS
HEAVY WATER
HYDROCARBONS
HYDROGEN
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
HYDROLYSIS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LIGHT NUCLEI
LYSIS
MESITYLENE
NONMETALS
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SOLVENTS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
REACTION KINETICS
SOLVENTS
SOLVOLYSIS
STABLE ISOTOPES
SULFONIC ACIDS
TOLUENE
WATER