Density functional study of the relative reactivity in the concerted 1,3-dipolar cycloaddition of nitrile ylide to disubstituted ethylenes

Hsin Yi Liao, Ming Der Su*, Wen-Sheng Chung, San Yan Chu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Density functional theory was used to perform a theoretical evaluation of (E)-1,2-disubstituted ethylenes as dipolarophiles for the 1,3-dipolar cycloaddition reaction. The reactivities of electron-withdrawing and -donating substituted ethylenes were examined by estimating their activation energies. The calculated activation energies predicted that the most reactive species is (E)-1,2-C2H2(NO)2, whereas the least reactive is (E)-2-butene. Namely, it was demonstrated that 16-electron, 1,3-dipole reactants with more electropositive substituents in terminal positions and ethylenes that possess more strongly electron-withdrawing substituents facilitate 1,3-dipolar cycloaddition reactions. All of the theoretical results can be rationalized using the configuration mixing model.

Original languageEnglish
Pages (from-to)318-323
Number of pages6
JournalInternational Journal of Quantum Chemistry
Volume83
Issue number6
DOIs
StatePublished - 5 Jul 2001

Keywords

  • 1,3-dipolar cycloaddition reaction
  • Configuration mixing model

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