DFT study on the cycloreversion of thietane radical cations

The Journal of Physical Chemistry. a
L R DomingoMiguel A Miranda

Abstract

The molecular mechanism of the cycloreversion (CR) of thietane radical cations has been analyzed in detail at the UB3LYP/6-31G* level of theory. Results have shown that the process takes place via a stepwise mechanism leading to alkenes and thiobenzophenone; alternatively, formal [4+2] cycloadducts are obtained. Thus, the CR of radical cations 1a,b(•+) is initiated by C2-C3 bond breaking, giving common intermediates INa,b. At this stage, two reaction pathways are feasible involving ion molecule complexes IMCa,b (i) or radical cations 4a,b(•+) (ii). Calculations support that 1a(•+) follows reaction pathway ii (leading to the formal [4+2] cycloadducts 5a). By contrast, 1b(•+) follows pathway i, leading to trans-stilbene radical cation (2b(•+)) and thiobenzophenone.

References

Jun 6, 2002·Journal of the American Chemical Society·Miguel A Miranda, M Angeles Izquierdo
Mar 5, 2003·Chemical Communications : Chem Comm·Miguel A Miranda, M Angeles Izquierdo
Dec 20, 2003·The Journal of Organic Chemistry·Raúl Pérez-RuizMiguel A Miranda
Feb 12, 2005·The Journal of Organic Chemistry·Raúl Pérez-RuizMiguel A Miranda
May 13, 2005·Organic & Biomolecular Chemistry·Marcus G FriedelThomas Carell
Jul 6, 2005·Chemical Communications : Chem Comm·Thorsten Stafforst, Ulf Diederichsen
Jan 6, 2006·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Raúl Pérez-RuizAxel G Griesbeck
Feb 8, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Luis R Domingo, Julia Pérez-Prieto
Jul 13, 2006·The Journal of Physical Chemistry. a·M Angeles IzquierdoMiguel A Miranda
Jan 30, 2007·Accounts of Chemical Research·Axel G GriesbeckKlaus-Dieter Warzecha
Feb 8, 2007·Chembiochem : a European Journal of Chemical Biology·Jérôme TrzcionkaMiguel Angel Miranda
Mar 29, 2007·The Journal of Physical Chemistry. a·O Anders BorgBo Durbeej
Jan 15, 2008·DNA Repair·Rob BeukersPaul H M Lohman
Feb 28, 2008·Chemical Reviews·Norbert Hoffmann
Jun 20, 2008·Chemical Reviews·Fabien Boussicault, Marc Robert
May 29, 2009·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sören DooseMarkus Sauer
Mar 27, 2010·Organic Letters·Juan Elias ArgüelloMiguel A Miranda
Oct 28, 2010·Journal of the American Chemical Society·Keyarash SadeghianMartin Schütz

❮ Previous
Next ❯

Citations

Apr 8, 2014·Accounts of Chemical Research·Raúl Pérez-RuizMiguel A Miranda

❮ Previous
Next ❯

Related Concepts

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.