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Solvent polarity and hydrogen bond effects on nucleophilic substitution reaction of 2-bromo-5-nitrothiophene with piperidine

✍ Scribed by Ali Reza Harifi-Mood; Masoud Rahmati; Mohammad Reza Gholami

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
157 KB
Volume
43
Category
Article
ISSN
0538-8066

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✦ Synopsis

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, k~A~, decreased sharply with n‐hexane content. The multiparameter correlation of log k~A~ 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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