Development of Molecular Mechanics Torsion Parameters for α,β-Cyclopropyl α′,β′-Enones and Conformational Analysis of Bicyclo[m.1.0]alk-3-en-2-ones

Eugene A Mash, Timothy M. Gregg, Matthew T. Stahl

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Conformations of cyclopropyl vinyl ketone have been studied using ab initio methods in an effort to quantify the effects of conjugative overlap between the cyclopropane ring and adjacent enone carbonyl. With respect to the cyclopropyl carbonyl torsion, cyclopropyl vinyl ketone exhibits a global energy minimum in the s-cis conformer and a local energy minimum in the s-trans conformer. The potential energy curve obtained was used to derive torsion parameters which were employed in molecular mechanics studies of the conformations of the set of bicyclo[m.1.0]alk-3-en-2-ones having larger ring sizes from 5- to 16-membered.

Original languageEnglish (US)
Pages (from-to)3715-3721
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number11
StatePublished - 1997

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Molecular mechanics
Ketones
Torsional stress
Conformations
Potential energy
cyclopropane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Development of Molecular Mechanics Torsion Parameters for α,β-Cyclopropyl α′,β′-Enones and Conformational Analysis of Bicyclo[m.1.0]alk-3-en-2-ones. / Mash, Eugene A; Gregg, Timothy M.; Stahl, Matthew T.

In: Journal of Organic Chemistry, Vol. 62, No. 11, 1997, p. 3715-3721.

Research output: Contribution to journalArticle

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AB - Conformations of cyclopropyl vinyl ketone have been studied using ab initio methods in an effort to quantify the effects of conjugative overlap between the cyclopropane ring and adjacent enone carbonyl. With respect to the cyclopropyl carbonyl torsion, cyclopropyl vinyl ketone exhibits a global energy minimum in the s-cis conformer and a local energy minimum in the s-trans conformer. The potential energy curve obtained was used to derive torsion parameters which were employed in molecular mechanics studies of the conformations of the set of bicyclo[m.1.0]alk-3-en-2-ones having larger ring sizes from 5- to 16-membered.

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