The [12]Annulene Global Minimum

The [12]Annulene Global Minimum

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 t...

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Veröffentlicht in:Journal of organic chemistry 2008-02, Vol.73 (4), p.1532-1535
Hauptverfasser: Braten, Miles N, Castro, Claire, Herges, Rainer, Köhler, Felix, Karney, William L
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Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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container_end_page 1535
container_issue 4
container_start_page 1532
container_title Journal of organic chemistry
container_volume 73
creator Braten, Miles N
Castro, Claire
Herges, Rainer
Köhler, Felix
Karney, William L
description 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.
doi_str_mv 10.1021/jo702412d
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subjects Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
title The [12]Annulene Global Minimum
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