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Theoretical study of 1,3-dipolar cycloaddition reactions between 7–10-membered simple cycloalkynes and triazoles R–N3 (R = H, CH3, Ph)

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Abstract

The energy contents in alkynes may be increased further by bending the normally linear triple bond, as in the small cycloalkynes. The strain energy in the cycloalkynes increases as the size of the ring decreases. Cycloadditions of 1,3-dipoles with alkynes occur by concerted mechanisms. In this study, the reactivity and strain energy effect of the cycloalkynes with substituted 1,2,3-triazoles R–N3 (R = H, CH3, and Ph) by the use of B3LYP/6-31G** level method will be discussed. The investigation of the structured properties, theoretical thermodynamic and kinetic data, i.e., ΔrG, ΔG* and rate constants of the reactions in 298 K will be presented.

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Acknowledgments

The corresponding author gratefully acknowledges the colleagues in Chemistry Department of The University of New England-Australia, for their useful suggestions. We have also acknowledged The Computational and Theoretical Research Center of Razi University, Kermanshah, Iran.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Razi University, P.O. Box 67149-67346, Kermanshah, Iran

    Avat Arman Taherpour

  2. Chemistry Department, Science Faculty, Islamic Azad University, P.O. Box 38135-567, Arak, Iran

    Elahe Rajaeian, Hadi Shafiei & Maryam Malekdar

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  1. Avat Arman Taherpour
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  2. Elahe Rajaeian
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  3. Hadi Shafiei
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  4. Maryam Malekdar
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Correspondence to Avat Arman Taherpour.

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Taherpour, A.A., Rajaeian, E., Shafiei, H. et al. Theoretical study of 1,3-dipolar cycloaddition reactions between 7–10-membered simple cycloalkynes and triazoles R–N3 (R = H, CH3, Ph). Struct Chem 24, 523–534 (2013). https://doi.org/10.1007/s11224-012-0105-0

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