Theoretical investigation of Banert cascade reaction

Royal Society Open Science
S Bhattacharyya, K Hatua

Abstract

Computational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2'-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is much faster than SN2' displacement in the order of 8. The [3,3]-sigmatropic rearrangement for the conversion of propargyl azide into triazafulvene has been proved as the rate-determining step having highest activation energy parameter. Solvent effect on total course of reaction has been found negligible. Furthermore, effects of different density functional theory functionals and functional groups on activation energies of [3,3]-sigmatropic rearrangement of propargyl azide were also studied. BHHLYP, ωB97XD, M062X and BMK calculated ΔG‡ are consistent with B3LYP.

References

Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
Apr 1, 2003·Journal of Computational Chemistry·Maurizio CossiVincenzo Barone
Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Jan 28, 2006·The Journal of Chemical Physics·Stefan Grimme
Nov 1, 2006·Angewandte Chemie·K C NicolaouPaul G Bulger
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Dec 27, 2008·Bioorganic & Medicinal Chemistry Letters·Nilkanth G AherManoj K Bhat
Oct 23, 2009·Chemical Society Reviews·K C Nicolaou, Jason S Chen
Sep 29, 2011·Chemistry, an Asian Journal·Sandip G AgalaveVandana S Pore
Apr 10, 2012·European Journal of Medicinal Chemistry·Christophe MenendezMichel Baltas
May 18, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Reginaldo G Lima-NetoJanaína V dos Anjos

❮ Previous
Next ❯

Citations

Apr 11, 2019·Organic & Biomolecular Chemistry·Angela S Carlson, Joseph J Topczewski
Apr 3, 2021·Organic Letters·Juliana R AlexanderJoseph J Topczewski
Apr 24, 2021·Chemical Communications : Chem Comm·J R AlexanderJ J Topczewski
Jan 17, 2020·The Journal of Organic Chemistry·Juliana R AlexanderJoseph J Topczewski

❮ Previous
Next ❯

Software Mentioned

BHHLYP
B3LYP
G09
B2PLYP
M062X
BMK

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.