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Effect of binary aqueous‐organic solvents on the reaction of phenacyl bromide with nitrobenzoic acid(s) in the presence of triethylamine
Author(s) -
Nallu M.,
Subramanian M.,
Vembu N.,
Akber Hussain A.
Publication year - 2004
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.20012
Subject(s) - chemistry , triethylamine , phenacyl bromide , solvation , aqueous solution , acetonitrile , solvent , solvent effects , acetone , dimethylformamide , reaction rate constant , inorganic chemistry , organic chemistry , kinetics , physics , quantum mechanics
Second‐order rate constants ( k 2 ) of the reaction between phenacyl bromide and equimolar mixture of nitrobenzoic acid(s)–triethylamine have been determined in dimethylformamide (DMF)/acetonitrile (ACN)/acetone and aqueous mixtures of these solvents by conductometric method at 30°C. The rates of nitrobenzoic acids are found to be in the order: 4‐NO 2 > 3‐NO 2 > 3,5‐(NO 2 ) 2 . Changes in the rate just by the addition of water (1% (v/v)) into organic component is rationalized. Decrease in the values of k 2 on increasing water content in organic solvent is explained on the basis of preferential solvation phenomenon. Single and dual regression analysis using the various solvent parameters of aqueous mixtures ( E T (30), Z , π*, β, α, and Y ) resulted in π* and α as the best parameters to explain solvation of nitrobenzoates. © 2004 Wiley Periodicals, Inc. Int J Chem Kinet 36: 401–409, 2004