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The kinetics of reaction of copper with substituted benzyl bromides in dipolar aprotic solvents
Author(s) -
Egorov Anatoly M.,
Matyukhova Svetlana A.,
Anisimov Alexander V.
Publication year - 2005
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20101
Subject(s) - chemistry , bromide , substituent , copper , dimethylacetamide , dimethyl sulfoxide , benzyl bromide , hammett equation , reaction rate constant , solvent , medicinal chemistry , kinetics , reaction rate , sulfoxide , inorganic chemistry , solvent effects , organic chemistry , polymer chemistry , catalysis , physics , quantum mechanics
The reaction of copper with benzyl bromides in dipolar aprotic solvents has been studied. There are no linear or other simple relations between ε, 1/ε, Y , P , n 20 D , and the rate of reaction. The activity of the solvent is determined by donor number (DN SbCl 5) in reaction under consideration. The kinetic and thermodynamic parameters of the reaction of copper with benzyl bromide in dimethyl sulfoxide (DMSO) have been clarified. Hammett plots of log ( k / k °) vs. the substituent constant σ gave good correlations (ρ = 0.18, S ρ = 0.02, r = 0.961 in dimethyl sulfoxide and ρ = 0.21, S ρ = 0.02, r = 0.947 in dimethylacetamide (DMAA)). The structure of the organic group has little effect on the rate of reaction of benzyl bromide with copper. The Hammett ρ value also depends on DN SbCl 5. © 2005 Wiley Periodicals, Inc. Int J Chem Kinet 37: 496–501, 2005