JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 2 (2016): Journal of the Chilean Chemical Society
Original Research Papers

EXPERIMENTAL AND THEORETICAL STUDY OF STABLE PHOSPHORUS YLIDES DERIVED FROM INDAZOLE IN THE PRESENCE OF DIFFERENT DIALKYL ACETYELENEDICARBOXYLATES: FURTHER INSIGHTS INTO THE REACTION MECHANISM

Mohammad Zakarianezhad
Department of Chemistry, Payam Noor University, Tehran
Batoul Makiabadi
Department of Chemical Engineering, Sirjan University of Technology, Sirjan
Motahare Shool
Department of Chemistry, Payam Noor University, Tehran
Vol 61, No 2 (2016): Journal of the Chilean Chemical Society
Published June 10, 2016
Keywords
  • NH-acid,
  • Kinetic investigation,
  • Theoretical study,
  • Z- and E-rotamers,
  • Indazole,
  • Triphenylphosphine
  • ...More
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How to Cite
Zakarianezhad, M., Makiabadi, B., & Shool, M. (2016). EXPERIMENTAL AND THEORETICAL STUDY OF STABLE PHOSPHORUS YLIDES DERIVED FROM INDAZOLE IN THE PRESENCE OF DIFFERENT DIALKYL ACETYELENEDICARBOXYLATES: FURTHER INSIGHTS INTO THE REACTION MECHANISM. Journal of the Chilean Chemical Society, 61(2). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/17

Abstract

In the recent work, kinetics studies were made of the reactions between triphenylphosphine 1, dialkyl acetylenedicarboxylates 2 in the presence of NH-acid, such as indazole 3. The kinetic parameters of all reactions determined by UV spectrophotometry. The second order fits were drawn and the values of the second order rate constant (k) were calculated using standard equations. All reactions repeated at different solvents and temperatures. Furthermore, useful information was obtained from studies of the effect of solvent, the structure of the reactants (dialkyl acetylenedicarboxylates) and also the concentration of reactants on the reaction rates. Theoretical studies were performed for evaluation of potential energy surfaces of all structures participated in the reaction mechanism. The first step of all reactions was recognized as a rate-determining step in the reaction mechanism, on the basis of experimental and theoretical data. Theoretical studies performed for evaluation of potential energy surfaces of all structures participated in the reaction mechanism. Quantum mechanical calculations were clarified that how the ylides exist, in solution, as a mixture of two geometrical Z- and E-isomers as a minor or major form.

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