Ab initio investigation of the structure and reactivity of vinyl ethers

M. Leibovitch, A. J. Kresge, M. R. Peterson, I. Csizmadia

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Extensive ab initio calculations have been performed on a series of methoxy-substituted ethylenes, namely methyl vinyl ether, 1,1- and cis- and trans-1,2-dimethoxyethene. Energies have been evaluated at the self-consistent field (SCF) molecular orbital level. Geometrical parameters have been optimized at 3-21G and/or 6-31G* basis sets. Calculations have also been performed on the products of protonation of these vinyl ethers on oxygen and β-carbon. Included in this report is discussion on, (a) the apparent cis-trans vinyl ether hydrolysis rate difference, (b) the attempt to reproduce the cis-trans 1,2-dimethoxyethene relative energy stability with the use of large extended basis sets, including electron correlation effects, and (c) β-carbon and ether oxygen protonation energetics in these gas phase calculations.

Original languageEnglish
Pages (from-to)349-385
Number of pages37
JournalJournal of Molecular Structure: THEOCHEM
Volume230
Issue numberC
DOIs
Publication statusPublished - May 24 1991

Fingerprint

Ethers
ethers
reactivity
Protonation
Ethylenes
Carbon
Oxygen
Methyl Ethers
Electron correlations
Molecular orbitals
Ether
Propylene
carbon
Hydrolysis
oxygen
Gases
Electrons
self consistent fields
hydrolysis
molecular orbitals

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Ab initio investigation of the structure and reactivity of vinyl ethers. / Leibovitch, M.; Kresge, A. J.; Peterson, M. R.; Csizmadia, I.

In: Journal of Molecular Structure: THEOCHEM, Vol. 230, No. C, 24.05.1991, p. 349-385.

Research output: Contribution to journalArticle

Leibovitch, M. ; Kresge, A. J. ; Peterson, M. R. ; Csizmadia, I. / Ab initio investigation of the structure and reactivity of vinyl ethers. In: Journal of Molecular Structure: THEOCHEM. 1991 ; Vol. 230, No. C. pp. 349-385.
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