Solvent polarity and hydrogen bond effects on nucleophilic substitution reaction of 2‐bromo‐5‐nitrothiophene with piperidine |
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| Authors: | Ali Reza Harifi‐Mood Masoud Rahmati Mohammad Reza Gholami |
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| Affiliation: | 1. Department of Chemistry, Tarbiat Moallem University, P.O. Box 15719‐14911, Karaj, Iran;2. Department of Chemistry, Sharif University of Technology, P.O. Box 11365‐9516, Tehran, Iran |
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| Abstract: | The reaction kinetics of 2‐bromo‐5‐nitro thiophene with piperidine was studied in a solvent with a mixture of propan‐2‐ol with methanol and n‐hexane at 25°C. The measured rate coefficients of the reaction demonstrated dramatic variations in propan‐2‐ol–n‐hexane mixtures and mild variations in propan‐2‐ol–methanol system. The second‐order rate coefficients of the reaction, kA, decreased sharply with n‐hexane content. The multiparameter correlation of log kA versus molecular‐microscopic solvent parameters shows interesting results in these solutions. Linear free energy relationship investigations confirm that polarity has a major effect on the reaction rate and hydrogen bond ability of the media has a slight effect on the reaction rate. © 2011 Wiley Periodicals, Inc. Int J Chem Kinet 43: 185–190, 2011 |
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