Quantum chemical studies on electrophilic addition - III. Reaction of hydroxonium ion with ethylene. Acid catalysed ring opening of epoxides

Alan C. Hopkinson, Min H. Lien, Imre G. Csizmadia, Keith Yates

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The geometries of the 2-hydroxyethyl and isomeric oxiranium cations have been fully optimized using ab initio molecular orbital calculations employing the split valence shell 4-31G basis set. These species are possible intermediates in both the electrophilic addition of OH⊕ to ethylene and in the acid catalysed ring opening of oxirane. The optimized structures were then used to compute more accurate wave functions using Dunning's double-zeta basis set, and with this large basis set the bridged oxiranium ion was found to be the more stable by 7.2 kcal/mole. The barrier to interconversion of these two C2H4OH⊕ ions was computed to be 25.0 kcal/mole above the oxiranium ion.

Original languageEnglish
Pages (from-to)97-109
Number of pages13
JournalTheoretica chimica acta
Volume47
Issue number2
DOIs
Publication statusPublished - Jun 1 1978

Keywords

  • Epoxides, acid catalysed ring opening of ∼
  • Hydroxonium ion, reaction of ∼ with ethylene

ASJC Scopus subject areas

  • Chiropractics

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