Substituent effects on stability of oxiranes, oxirenes, and dioxiranes

Research output: Contribution to journalArticle

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Abstract

Homodesmotic reactions were designed to study substituent effects on stability of oxiranes, oxirenes, and dioxiranes. Good or fair correlation between their homodesmotic stabilization energies and Taft's dual-substituent-parameters has been found. Oxiranes are stabilized by σ-donating and π-donating substituents but destabilized by σ-accepting and π-accepting substituents. The π-effects on oxiranes are comparable to σ- effects for π-acceptor substituents and are much stronger than σ-effects for π-donor substituents. Oxirenes are stabilized by σ-donating, π-donating, and π-accepting substituents but destabilized by σ-accepting substituents. The π-effects on oxirenes are stronger than σ-effects. Oxirenes with strong π- donor substituents such as F, OH, and NH 2 , or strong σ-donor substituents such as L and Na are neither real molecules nor transition states. Dioxiranes are stabilized by σ-donating and π-donating substituents but destabilized by σ-accepting and π- accepting substituents. The π-effects on dioxiranes are stronger than σ-effects for π-donor substituents, but weaker than σ- effects for π-acceptor substituents.

Original languageEnglish
Pages (from-to)562-567
Number of pages6
JournalCanadian Journal of Chemistry
Volume78
Issue number5
DOIs
Publication statusPublished - 2000 Jan 1

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Epoxy Compounds
Stabilization
Molecules
dioxirane

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

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Substituent effects on stability of oxiranes, oxirenes, and dioxiranes. / Sung, Kuang-Sen.

In: Canadian Journal of Chemistry, Vol. 78, No. 5, 01.01.2000, p. 562-567.

Research output: Contribution to journalArticle

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