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Mechanisms of 5'-O-Benzoyl-2,3'-anhydrothymidine Reactions with Nucleophiles: IV.* Kinetics and Thermodynamics of Azidation with Dimethylammonium Azide in DMF-1,4-Dioxane

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Abstract

The reaction of 5'-O-benzoyl-2,3'-anhydrothymidine with dimethylammonium azide in the system DMF-1,4-dioxane in the temperature range from 80 to 100°C follows the overall second-order kinetics and first-order kinetics with respect to each reactant. The activation parameters in the systems containing 30, 40, and 50 vol % of dioxane are, respectively: ΔH ≠298 99, 85, and 79 kJ mol- 1; ΔS ≠298 -46, -83, and -101 J mol- 1 K- 1. A refined model of the transition state for the rate-determining stage was proposed, which takes into account specific interaction with 1,4-dioxane.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii, pr. 26, St. Petersburg, 198013, Russia

    E. V. Korchevskaya, Yu. V. Ostrovskii, A. A. Malin, M. Z. Trukhanovich, M. B. Shcherbinin & V. A. Ostrovskii

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  1. E. V. Korchevskaya
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  2. Yu. V. Ostrovskii
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  3. A. A. Malin
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  4. M. Z. Trukhanovich
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  5. M. B. Shcherbinin
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  6. V. A. Ostrovskii
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Korchevskaya, E.V., Ostrovskii, Y.V., Malin, A.A. et al. Mechanisms of 5'-O-Benzoyl-2,3'-anhydrothymidine Reactions with Nucleophiles: IV.* Kinetics and Thermodynamics of Azidation with Dimethylammonium Azide in DMF-1,4-Dioxane. Russian Journal of Organic Chemistry 38, 735–737 (2002). https://doi.org/10.1023/A:1019627509596

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  • DOI: https://doi.org/10.1023/A:1019627509596

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