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Theoretical Calculation of Thermodynamic and Kinetic Quantities for 1,3 Dipolar Cycloaddition Reactions Between Nitrile Sulfides R–CNS (R = H, CH3, Ph and Ph(CH3)3) with 7–10 Membered Simple Cycloalkynes

  • Elahe Rajaeian
  • Elham Mirzaei
  • Avat Arman TaherpourEmail author
Research Paper

Abstract

The 1,3-dipolar cycloaddition reactions also known as the Huisgen cycloaddition are one of the most widely used and versatile preparative methods in hetrocyclic chemistry. In this study, the reactivity and strain energy effect of the simple cycloalkynes with substituted Nitrile sulfides R–CNS (R = H, CH3, Ph and Ph(CH3)3) will be discussed in light of computational studies using DFT methods (B3LYP/6-31G*). The investigation of the structured properties, theoretical thermodynamic and kinetic data of the reactions in 298 K will be presented. The results show increase in the ∆G* by increasing the ring size and decreasing the strain energy of cycloalkynes. Also, the rate constants and the free energy changes in reactions increase as the size of the ring decreases. The relationships of the deviation of the internal bond angle (DIBA, in degrees), π-strain (S π ) (in kcal mol−1), the bond angle of Csp3–C ≡ C (θº) and ΔG #(kcal mol−1) for the series of cycloalkynes I-1 to I-4 have investigated.

Keywords

Isothiazole Cycloalkynes Nitrile sulfide 1,3-dipolar cycloaddition reaction DFT-B3LYP Molecular orbital calculations Ab initio 

Notes

Acknowledgments

The corresponding author gratefully acknowledges from Theoretical and Computational Research Center of Chemistry Faculty of Razi University-Kermanshah-Iran, The authors gratefully acknowledge the Medical Biology Research Center and Kermanshah University of Medical Sciences, Kermanshah.

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Copyright information

© Shiraz University 2016

Authors and Affiliations

  • Elahe Rajaeian
    • 1
  • Elham Mirzaei
    • 1
  • Avat Arman Taherpour
    • 2
    • 3
    Email author
  1. 1.Chemistry Department, Science FacultyIslamic Azad University, Arak BranchArakIran
  2. 2.Department of Organic Chemistry, Faculty of ChemistryRazi UniversityKermanshahIran
  3. 3.Medical Biology Research CenterKermanshah University of Medical SciencesKermanshahIran

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