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Francesca D'Anna1, Sandra La Marca, Renato Noto

  • 1Dipartimento di Chimica Organica E. Paternò, Università degli Studi di Palermo, Viale delle Scienze, Parco d'Orleans II, 90128 Palermo, Italy. fdanna@unipa.it; rnoto@unipa.it

The Journal of Organic Chemistry
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Summary

The Kemp elimination of benzisoxazole is influenced by amine structure and ionic liquid properties. Reaction rates vary with amine type and ionic liquid composition, suggesting an "early" transition state.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • The Kemp elimination involves the amino-induced elimination of benzisoxazole to form o-cyanophenolate.
  • Ionic liquids (ILs) are versatile solvents with tunable properties, impacting reaction kinetics.

Purpose of the Study:

  • To investigate the kinetics of the Kemp elimination in ionic liquids.
  • To understand the influence of amine structure and ionic liquid properties on the reaction rate.
  • To explore the role of solvent effects and determine activation parameters.

Main Methods:

  • The study employed kinetic measurements of the Kemp elimination reaction.
  • Varied temperatures (293-313 K) and different primary, secondary, and tertiary amines were used.
  • The reaction was conducted in various ionic liquids, including [bmim][BF4], [bmim][PF6], [bmim][NTf2], [bm2im][NTf2], and [bmpyrr][NTf2].
  • Solvent effects of methanol and [bmim][NTf2] were also assessed.

Main Results:

  • Amine structure significantly affects the reaction rate of the Kemp elimination.
  • Different ionic liquids and their structural variations (cation/anion) influence reaction kinetics.
  • A notable effect on the reaction rate was observed with H-donor negative solvents like methanol and [bmim][NTf2].
  • A narrow range of activation parameters was calculated for reactions involving various amines and ILs.

Conclusions:

  • The structure of the amine plays a critical role in determining the rate of the Kemp elimination.
  • The properties of the ionic liquid, influenced by cation and anion structure, significantly impact the reaction.
  • The calculated activation parameters suggest the reaction proceeds through an early transition state.