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Solvatochromic Parameters Effects Study on Kinetics of Aromatic Nucleophilic substitution reaction in mixture of Ionic liquid and alcoholic solvents

Salari, Hadi | 2009

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 39974 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Gholami, Mohammad Reza
  7. Abstract:
  8. Solute-solvent and solvent-solvent interactions were investigated in mixtures of 2-hydroxy ethylammonium formate with methanol, ethylene glycol and glycerol. Solvatochromic parameters, including normalized polarity ( ), dipolarity/polarizability (π*), hydrogen-bond donor (α), and hydrogen-bond acceptor (β) abilities, were determined in these mixtures. parameters showed synergetic effects in mixtures of ionic liquid and alcohols due to the preferential solvation. Experimental data were handled in Redlich-Kister model and demonstrated a fair correlation with predicted data. Solvent effects on reaction kinetics were studied in aromatic nucleophilic substitution reaction of 2-Chloro-3,5- dinitropyridine with aniline in mixture of ionic liquid and alcoholic solvents. It was shown that ionic liquid addition increase the rate of reaction abruptly. In ionic liquid mixtures no change in mechanism and rate determination step observed. The results were analyzed using the Abraham-Kamlet-Taft model. In aromatic nucleophilic substitution reaction, α and β demonstrated an opposite effect on rate constant of the reaction in ionic liquid-glycerol mixtures. α and β showed a positive and a negative effect on increasing on the rate constant, respectively. α and π* in ionic liquid-methanol mixtures demonstrated a parallel effect on increasing of the rate constant. We observed similar behavior for β and π* in ionic liquid-ethylene glycol mixtures. Polar effects and hydrogen bonding interactions increase coherently the reaction rate in ionic liquid mixtures.
  9. Keywords:
  10. Solvatochromic Properties ; Solute-Solvent Interaction ; Arommatic Nucleophilic Substitution Reaction ; Solvent Effect ; Ionic Liquids

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