Effect of medium polarity on the kinetics of electrophilic Isotopic substitution reactions of hydrogen atoms in aromatic amines with a carboxylic acid

Journal Article · Sun Nov 10 04:00:00 EST 1985 · J. Gen. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7031937

Serebryanskaya, A I; Kurenkova, V M

This paper deals with the nature of solvation effects and intermolecular interactions involving a phenylamine of intermediate basicity, namely methlydiphenylamine, in reactions with trifluoroacetic acid alone, and in mixtures of trifluoroacetic acid with a wide range of aprotic solvents differing greatly in their polarity and electron donating properties. These studies allow one to dissect and elucidate the effects due to solvent or substrate acidity as well as the overriding importance of medium polarity. For the least protophilic (basic) amine studied, namely, triphenylamine, the deactivation of the acid via hydrogen bonding to the solvent was the most important factor governing the reaction kinetics.

• Research Organization: Varpov Sci-Res. Institute of Physical Chemistry, Moscow
• OSTI ID: 7031937
• Journal Information: J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 55:5,PT.2; ISSN JGCHA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
ACETIC ACID ESTERS
AMINES
ANILINE
AROMATICS
CARBOXYLIC ACID ESTERS
CHEMICAL REACTION KINETICS
DEUTERIUM
ELEMENTS
ESTERS
HIGH TEMPERATURE
HYDROGEN
HYDROGEN ISOTOPES
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LIGHT NUCLEI
NONMETALS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PH VALUE
REACTION KINETICS
SOLVATION
STABLE ISOTOPES