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Solute-solvent interaction effects on second-order rate constants of reaction between 1-chloro-2,4-dinitrobenzene and aniline in alcohol-water mixtures

Harati, M ; Sharif University of Technology | 2005

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  1. Type of Document: Article
  2. DOI: 10.1002/kin.20041
  3. Publisher: 2005
  4. Abstract:
  5. The second-order rate coefficients for aromatic nucleophilic substitution reaction between 1-chloro-2,4-dinitrobenzene and aniline have been measured in aqueous solutions of ethanol and methanol at 25°C. The plots of rate constants versus mole fraction of water show a maximum in all-aqueous solutions. The effect of four empirical solvent parameters including hydrogen bond donor acidity (α), dipolarity/polarizability (π*). normalized polarity (ETN), and solvophobicity (Sp) has been investigated. This investigation has been carried out by means of simple and multiple regression models A dual-parameter equation of log k2 versus Sp and α was obtained in all-aqueous solutions (n = 41, r = 0.962, s =0.053, p = 0.0000). This equation shows that solvophobicity and hydrogen bond donor acidity are important factors in the occurrence of the reaction and they have opposite effects on reaction rate. © 2004 Wiley Periodicals. Inc
  6. Keywords:
  7. Acidity ; Alcohols ; Aromatic compounds ; Complexation ; Hydrogen bonds ; Hydrophobicity ; Mathematical models ; Rate constants ; Regression analysis ; Substitution reactions ; Hydrogen-bond doner (HBD) ; Liquid phase reactions ; Piperidine ; Solvophobicity ; Solvents
  8. Source: International Journal of Chemical Kinetics ; Volume 37, Issue 2 , 2005 , Pages 90-97 ; 05388066 (ISSN)
  9. URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/kin.20041