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

Harifi Mood, A. R ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1002/kin.20547
  3. Abstract:
  4. 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
  5. Keywords:
  6. Hydrogen-bond effect ; Linear free energy relationships ; Multiparameters ; N-Hexane ; N-hexane mixture ; Nucleophilic substitution reactions ; Rate coefficients ; Second orders ; Solvent parameter ; Solvent polarity ; Hydrogen ; Hydrogen bonds ; Methanol ; Reaction rates ; Solvents ; Substitution reactions ; Thiophene ; Hexane
  7. Source: International Journal of Chemical Kinetics ; Volume 43, Issue 4 , 2011 , Pages 185-190 ; 05388066 (ISSN)
  8. URL: http://onlinelibrary.wiley.com/doi/10.1002/kin.20547/abstract;jsessionid=0650F1459934FD0F264CB0559BE98F4B.f04t03