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MAP  >  Progress in Reaction Kinetics and Mechanism
2023 Volume 48
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Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol

  • Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt

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  • Corresponding author: Magda F Fathalla, Department of Chemistry, Faculty of Science, Alexandria University, P.O. 426 Ibrahimia, Alexandria 21321, Egypt. Email: mffathalla@hotmail.com 
  • The reactions of 5- and 7-substituted isatin derivatives (H, Me, Cl, Br) with piperidine in 80% aqueous methanol gave the corresponding 1-(2'-amino-5'- or 3'- substituted phenyl)-2-(piperidin-1-yl) ethane-1, 2-dione derivatives. The reaction is proceeded through nucleophilic attack on C-2 followed by ring opening process. The reaction showed a second order and the isokinetic temperature is 169 K indicating that the reaction is entropy controlled. The constant ∆G# value, the linear plot of ∆H# versus ∆S#, plot of log kN values at high temperature versus those at low temperatures indicated that a unified mechanism of the reactions for all substituents. The σ°-Taft's constants are linearly correlated with log kN values and the ρ values are (2.01–1.86) pointing out that inductive effect of substituent is predominant and the rate-limiting is the breakdown of the tetrahedral intermediate T− and the ring opening is catalyzed by water.

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    Mohamed A El-Rahman, Mahmoud F Ibrahim, Magda F Fathalla, Samir K El-Sadany, Ezzat A Hamed, Alaa Z Omar. 2023. Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol. Progress in Reaction Kinetics and Mechanism. 48:14686783231218882 doi: 10.1177/14686783231218882
    Mohamed A El-Rahman, Mahmoud F Ibrahim, Magda F Fathalla, Samir K El-Sadany, Ezzat A Hamed, Alaa Z Omar. 2023. Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol. Progress in Reaction Kinetics and Mechanism. 48:14686783231218882 doi: 10.1177/14686783231218882
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Article   Open Access    

Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol

  • Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt

  • Corresponding author: Magda F Fathalla, Department of Chemistry, Faculty of Science, Alexandria University, P.O. 426 Ibrahimia, Alexandria 21321, Egypt. Email: mffathalla@hotmail.com 
Progress in Reaction Kinetics and Mechanism  48,  Article number: 10.1177/14686783231218882  (2023)  |  Cite this article

Abstract: The reactions of 5- and 7-substituted isatin derivatives (H, Me, Cl, Br) with piperidine in 80% aqueous methanol gave the corresponding 1-(2'-amino-5'- or 3'- substituted phenyl)-2-(piperidin-1-yl) ethane-1, 2-dione derivatives. The reaction is proceeded through nucleophilic attack on C-2 followed by ring opening process. The reaction showed a second order and the isokinetic temperature is 169 K indicating that the reaction is entropy controlled. The constant ∆G# value, the linear plot of ∆H# versus ∆S#, plot of log kN values at high temperature versus those at low temperatures indicated that a unified mechanism of the reactions for all substituents. The σ°-Taft's constants are linearly correlated with log kN values and the ρ values are (2.01–1.86) pointing out that inductive effect of substituent is predominant and the rate-limiting is the breakdown of the tetrahedral intermediate T− and the ring opening is catalyzed by water.

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    Cite this article
    Mohamed A El-Rahman, Mahmoud F Ibrahim, Magda F Fathalla, Samir K El-Sadany, Ezzat A Hamed, Alaa Z Omar. 2023. Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol. Progress in Reaction Kinetics and Mechanism. 48:14686783231218882 doi: 10.1177/14686783231218882
    Mohamed A El-Rahman, Mahmoud F Ibrahim, Magda F Fathalla, Samir K El-Sadany, Ezzat A Hamed, Alaa Z Omar. 2023. Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol. Progress in Reaction Kinetics and Mechanism. 48:14686783231218882 doi: 10.1177/14686783231218882
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