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[14]Annulene: cis/trans isomerization via two-twist and nondegenerate planar bond shifting and Möbius conformational minima.

Authors
  • Okoronkwo, Tobechi
  • Nguyen, Phuong T
  • Castro, Claire
  • Karney, William L
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Mar 05, 2010
Volume
12
Issue
5
Pages
972–975
Identifiers
DOI: 10.1021/ol100025j
PMID: 20121256
Source
Medline
License
Unknown

Abstract

Mechanisms linking dihydrooctalenes and the corresponding [14]annulene isomers have been investigated computationally. CCSD(T)/cc-pVDZ//BHLYP/6-31G* calculations suggest that the cis/trans isomerization steps required by these mechanisms can occur with reasonable activation barriers by pi-bond shifting, in some cases with two-twist topology, and in others in a planar but nondegenerate fashion. In addition, numerous Mobius conformational minima were located for [14]annulene isomers directly related to the mechanisms studied.

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