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The [12]annulene global minimum.

Authors
  • Braten, Miles N
  • Castro, Claire
  • Herges, Rainer
  • Köhler, Felix
  • Karney, William L
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Feb 15, 2008
Volume
73
Issue
4
Pages
1532–1535
Identifiers
DOI: 10.1021/jo702412d
PMID: 18198891
Source
Medline
License
Unknown

Abstract

A new global minimum for [12]annulene has been computationally located. This mono-trans minimum 5 (CCCCCT) is computed to be 1.5 kcal/mol more stable (CCSD(T)/cc-pVDZ//BHHLYP/6-311+G**) than the known tri-trans isomer 1 (CTCTCT) and 2.4 kcal/mol lower than the di-trans isomer 4 (CCTCCT), for which there is indirect evidence. The barriers for several rearrangements of 5 were all computed to be above 15 kcal/mol, indicating that direct experimental characterization of 5 should be possible. The computed barriers for the dynamic processes (including conformational automerization) coupled with computed 1H NMR shift values should aid in the future characterization of this [12]annulene isomer.

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