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.
- Epoxides, acid catalysed ring opening of ∼
- Hydroxonium ion, reaction of ∼ with ethylene
ASJC Scopus subject areas