A molecular orbital study of the reactions of sydnones

Edward B Roche, L. B. Kier

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

MO calculations using the ω Hückel LCAO technique have been performed on several 3-alkylsdnones. Energy calculatioins permit predictions for protonation of the number 2 N-atom, nucleophilic attack at the number 5 C-atom, electrophilic attack at the number 4 C-atom, and free-radical attack at the number 4 C-atom. Supporting evidence for these predictions is discussed, and mechanisms of base- and acid-catalyzed hydrolysis are proposed.

Original languageEnglish (US)
Pages (from-to)1673-1685
Number of pages13
JournalTetrahedron
Volume24
Issue number4
DOIs
StatePublished - Jan 1 1968

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Sydnones
Molecular orbitals
Free Radicals
Hydrolysis
Atoms
Acids
Protonation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A molecular orbital study of the reactions of sydnones. / Roche, Edward B; Kier, L. B.

In: Tetrahedron, Vol. 24, No. 4, 01.01.1968, p. 1673-1685.

Research output: Contribution to journalArticle

Roche, Edward B ; Kier, L. B. / A molecular orbital study of the reactions of sydnones. In: Tetrahedron. 1968 ; Vol. 24, No. 4. pp. 1673-1685.
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