Xiao-fang Chen, Kun Yang, Ke-li Han . Theoretical Study of 1,3-Dipolar Cycloaddition of Hydrazoic Acid to Substituted Ynamines[J]. Chinese Journal of Chemical Physics , 2009, 22(2): 143-148. doi: 10.1088/1674-0068/22/02/143-148
Citation: Xiao-fang Chen, Kun Yang, Ke-li Han . Theoretical Study of 1,3-Dipolar Cycloaddition of Hydrazoic Acid to Substituted Ynamines[J]. Chinese Journal of Chemical Physics , 2009, 22(2): 143-148. doi: 10.1088/1674-0068/22/02/143-148

Theoretical Study of 1,3-Dipolar Cycloaddition of Hydrazoic Acid to Substituted Ynamines

doi: 10.1088/1674-0068/22/02/143-148
Funds:  This work was supported by the National Natural Science Foundation of China (No.20833008).
  • Received Date: 2009-01-23
  • The 1,3-dipolar cycloaddition reactions of various substituted ynamines with hydrazoic acid were theoretically investigated with the high-accuracy CBS-QB3 method. Two regioisomers,4-amine, and 5-amine substituted adducts, were obtained, with the former as the preferred yield. This regioselectivity is rationalized by the frontier molecular orbital theory.The reactivity and synchronicity are enhanced with the increase of the electron-withdrawing character of the substitute on ynamine fragment. The calculations also show that the effect of solvent increases the activation energy, and the reaction becomes even harder in polar solvent.
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Theoretical Study of 1,3-Dipolar Cycloaddition of Hydrazoic Acid to Substituted Ynamines

doi: 10.1088/1674-0068/22/02/143-148
Funds:  This work was supported by the National Natural Science Foundation of China (No.20833008).

Abstract: The 1,3-dipolar cycloaddition reactions of various substituted ynamines with hydrazoic acid were theoretically investigated with the high-accuracy CBS-QB3 method. Two regioisomers,4-amine, and 5-amine substituted adducts, were obtained, with the former as the preferred yield. This regioselectivity is rationalized by the frontier molecular orbital theory.The reactivity and synchronicity are enhanced with the increase of the electron-withdrawing character of the substitute on ynamine fragment. The calculations also show that the effect of solvent increases the activation energy, and the reaction becomes even harder in polar solvent.

Xiao-fang Chen, Kun Yang, Ke-li Han . Theoretical Study of 1,3-Dipolar Cycloaddition of Hydrazoic Acid to Substituted Ynamines[J]. Chinese Journal of Chemical Physics , 2009, 22(2): 143-148. doi: 10.1088/1674-0068/22/02/143-148
Citation: Xiao-fang Chen, Kun Yang, Ke-li Han . Theoretical Study of 1,3-Dipolar Cycloaddition of Hydrazoic Acid to Substituted Ynamines[J]. Chinese Journal of Chemical Physics , 2009, 22(2): 143-148. doi: 10.1088/1674-0068/22/02/143-148

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