The [12]annulene global minimum

The Journal of Organic Chemistry
Miles N BratenWilliam L Karney

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.

References

Nov 17, 2001·Chemical Reviews·K B Wiberg
Sep 27, 2002·Organic Letters·Claire CastroPaul von Ragué Schleyer
Aug 13, 2004·Angewandte Chemie·Chaitanya S WannerePaul von Ragué Schleyer
Apr 23, 2005·The Journal of Organic Chemistry·Claire CastroMiguel A Valencia
Jul 7, 2005·Journal of the American Chemical Society·Claire CastroRyan P Pemberton
Dec 7, 2006·Journal of the American Chemical Society·Matthew K KiesewetterCheryl D Stevenson
Dec 15, 2006·Chemical Reviews·Eric L SpitlerMichael M Haley
Dec 21, 2006·Journal of the American Chemical Society·Ryan P PembertonWilliam L Karney

❮ Previous
Next ❯

Citations

Aug 19, 2016·Chemical Reviews·Takayuki Tanaka, Atsuhiro Osuka
Jun 21, 2014·Nature Chemistry·Gaston R SchallerRainer Herges
May 1, 2009·Nature Chemistry·Zin Seok YoonDongho Kim
Feb 13, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Irene Casademont-ReigEduard Matito
Dec 20, 2012·Chemical Communications : Chem Comm·Gaston R Schaller, Rainer Herges
Jul 3, 2010·The Journal of Organic Chemistry·Eva-Katrin MuckeRainer Herges
Apr 28, 2012·Journal of the American Chemical Society·Andrey Yu RogachevRoald Hoffmann

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.