The proton transfer reaction between bis(2,4-dinitrophenyl)methane and nitrogen bases in dimethyl sulfoxide and toluene solvents

Autor:	Arnold Jarczewski, Grzegorz Schroeder, Kenneth T. Leffek
Rok vydání:	1991
Předmět:	Tertiary amine Chemistry Dimethyl sulfoxide Organic Chemistry Sulfoxide General Chemistry Medicinal chemistry Toluene Catalysis chemistry.chemical_compound Reaction rate constant Kinetic isotope effect Organic chemistry Solvent effects Equilibrium constant
Zdroj:	Canadian Journal of Chemistry. 69:468-473
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v91-070
Popis:	Rate constants have been measured for the proton and deuteron transfer reactions of bis(2,4-dinitrophenyl)methane (1) with 1,1,3,3-tetramethylguanidine (TMG) and 1,5-diazabicyclo[5.4.0]undec-7-ene (DBU) in dimethyl sulfoxide (DMSO) and toluene solvents. Equilibrium constants, primary deuterium kinetic isotope effects, and activation parameters are reported. The reaction of 1 with DBU is faster than that with TMG by factors of 5 and 50 in toluene and DMSO respectively. The primary deuterium kinetic isotope effects, kH/kD = 7–9, which are independent of the polarity of the solvent, indicate an uncoupled mechanism of proton transfer and are in the "classical" region with little or no indication of a tunnelling contribution to the enthalpy of activation for these reactions. Key words: proton transfer, bis(2,4-dinitrophenyl)methane, deuterium isotope effects.
Databáze:	OpenAIRE
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