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Solvent polarity and hydrogen bond effects on nucleophilic substitution reaction of 2‐bromo‐5‐nitrothiophene with piperidine
Author(s) -
HarifiMood Ali Reza,
Rahmati Masoud,
Gholami Mohammad Reza
Publication year - 2011
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.20547
Subject(s) - chemistry , piperidine , hexane , solvent , methanol , nucleophilic substitution , reaction rate , solvent effects , hydrogen bond , kinetics , medicinal chemistry , organic chemistry , computational chemistry , molecule , catalysis , physics , quantum mechanics
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