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Kinetics of reaction of copper with substituted benzyl chlorides in dipolar aprotic solvents
Author(s) -
Egorov Anatoly M.,
Matyukhova Svetlana A.
Publication year - 2007
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.20266
Subject(s) - chemistry , substituent , copper , dimethylacetamide , hexamethylphosphoramide , hammett equation , benzyl chloride , reaction rate constant , solvent , solvent effects , inorganic chemistry , halogen , medicinal chemistry , kinetics , photochemistry , organic chemistry , catalysis , physics , alkyl , quantum mechanics
The reaction of copper with benzyl chlorides in dipolar aprotic solvents has been investigated. The kinetic and thermodynamic parameters of the reaction of copper with benzyl chloride in dimethyl sulfoxide, dimethylacetamide, and hexamethylphosphoramide have been obtained. Hammett plots of log ( k / k °) versus the substituent constant σ gave good correlation. The structure of the organic group has little effect on the rate of reaction of benzyl chloride with copper. The kinetic and thermodynamic parameters were correlated with donor number of solvent (DN SbCl 5). The ratio k RBr / k RCl and Hammett ρ values provide evidence in favor of the halogen atom transfer mechanism. © 2007 Wiley Periodicals, Inc. Int J Chem Kinet 39: 547–555, 2007