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Effect of solvents and effect of nucleophiles in nucleophilic substitution on benzyl bromide—A kinetic study
Author(s) -
Manikyamba P.,
Sundaram E. V.
Publication year - 1990
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.550221105
Subject(s) - chemistry , nucleophile , acetonitrile , bromide , solvent , solvation , thiourea , reagent , benzyl bromide , solvent effects , nucleophilic substitution , reaction rate constant , kinetics , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , physics , quantum mechanics
The kinetics of the reaction of benzyl bromide with thiourea was studied in different pure (protic and aprotic) solvents and the rate data was correlated using linear multiple regression analysis. From the regression coefficients which describe the susceptibility of rate to different solvent parameters, information regarding the solvent‐reagent, and the solvent‐intermediate interactions was obtained and solvation models were proposed. Applicability of the Swain‐Scott free energy relationship was tested using different sulphur nucleophiles in acetonitrile solvent and the nucleophilicity constant of N ‐acetylthiourea was computed as 2.74 from the regression line.