Quantum chemical studies on electrophilic addition - IV. Reaction of the nitrenium ion with ethylene and a comparison of the effectiveness of NH2, OH, F, Cl and SH as bridging substituents

Alan C. Hopkinson, Min H. Lien, I. Csizmadia, Keith Yates

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16 Citations (Scopus)

Abstract

The geometries of the 2-aminoethyl cation and the isomeric protonated aziridine have been optimized using ab initio molecular orbital calculations employing the split-valence shell 4-31G basis set. The protonated aziridine is computed to be the more stable ion by 46.5 kcal/mole (4-31G level) and 44.9 kcal/mole (double-zeta basis set). The profile to interconversion is found to have a barrier of less than 15 kcal/mole (relative to the 2-aminoethyl cation) and this profile is compared with those computed for the similar ions XCH2CH2+where X=OH, F, SH and Cl.

Original languageEnglish
Pages (from-to)1-14
Number of pages14
JournalTheoretica Chimica Acta
Volume55
Issue number1
DOIs
Publication statusPublished - Mar 1980

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Cations
ethylene
Ions
Orbital calculations
Molecular orbitals
cations
ions
profiles
Geometry
molecular orbitals
valence
geometry
aziridine

Keywords

  • 2-aminoethyl cation
  • Aziridine, protonated ∼

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

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abstract = "The geometries of the 2-aminoethyl cation and the isomeric protonated aziridine have been optimized using ab initio molecular orbital calculations employing the split-valence shell 4-31G basis set. The protonated aziridine is computed to be the more stable ion by 46.5 kcal/mole (4-31G level) and 44.9 kcal/mole (double-zeta basis set). The profile to interconversion is found to have a barrier of less than 15 kcal/mole (relative to the 2-aminoethyl cation) and this profile is compared with those computed for the similar ions XCH2CH2+where X=OH, F, SH and Cl.",
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T1 - Quantum chemical studies on electrophilic addition - IV. Reaction of the nitrenium ion with ethylene and a comparison of the effectiveness of NH2, OH, F, Cl and SH as bridging substituents

AU - Hopkinson, Alan C.

AU - Lien, Min H.

AU - Csizmadia, I.

AU - Yates, Keith

PY - 1980/3

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N2 - The geometries of the 2-aminoethyl cation and the isomeric protonated aziridine have been optimized using ab initio molecular orbital calculations employing the split-valence shell 4-31G basis set. The protonated aziridine is computed to be the more stable ion by 46.5 kcal/mole (4-31G level) and 44.9 kcal/mole (double-zeta basis set). The profile to interconversion is found to have a barrier of less than 15 kcal/mole (relative to the 2-aminoethyl cation) and this profile is compared with those computed for the similar ions XCH2CH2+where X=OH, F, SH and Cl.

AB - The geometries of the 2-aminoethyl cation and the isomeric protonated aziridine have been optimized using ab initio molecular orbital calculations employing the split-valence shell 4-31G basis set. The protonated aziridine is computed to be the more stable ion by 46.5 kcal/mole (4-31G level) and 44.9 kcal/mole (double-zeta basis set). The profile to interconversion is found to have a barrier of less than 15 kcal/mole (relative to the 2-aminoethyl cation) and this profile is compared with those computed for the similar ions XCH2CH2+where X=OH, F, SH and Cl.

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