Molecular recognition of pyrazine N,N'-dioxide using aryl extended calix[4]pyrroles.

Chemical Science
Chenxing GuoJonathan L Sessler

Abstract

Calix[4]pyrrole (C4P)-based systems have been extensively explored as binding agents for anions and ion pairs. However, their capacity to act as molecular containers for neutral species remains underexplored. We report here the molecular recognition of pyrazine N,N'-dioxide (PZDO) using a series of aryl extended C4Ps including three α,α-diaryl substituted C4Ps (receptors 1-3), an α,β-diaryl substituted C4P (receptor 4) and an α,α,α,α-tetraaryl substituted C4P (receptor 5). Single crystal structural analyses of the 2 : 1 host-guest complexes between receptors 1-3 and PZDO revealed that the C4P subunits exist in an unusual partial cone conformation and that the PZDO guest is held within electron-rich cavities formed by the lower rims of the individual C4P macrocycle. In contrast, receptor 5 was seen to adopt the cone conformation in the solid state, allowing one PZDO molecule to be accommodated inside the upper-rim cavity. Evidence for guest-directed self-assembly is also seen in the solid state. Evidence for C4P-PZDO interactions in CD3CN/CD3OD solution came from 1H NMR spectroscopic titrations. Electrostatic potential maps created by means of density functional theory calculations were constructed. Density functional theory cal...Continue Reading

References

May 26, 2001·The Journal of Organic Chemistry·Y D WuJ L Sessler
Mar 20, 2003·Angewandte Chemie·Emmanuel A MeyerFrançois Diederich
Feb 17, 2009·Journal of the American Chemical Society·Begoña VerdejoPablo Ballester
Feb 6, 2010·Journal of the American Chemical Society·Guzmán Gil-RamírezPablo Ballester
Dec 14, 2011·Proceedings of the National Academy of Sciences of the United States of America·Jung Su ParkJonathan L Sessler
Mar 21, 2012·Journal of the American Chemical Society·Virginia ValderreyPablo Ballester
Nov 2, 2012·Organic Letters·Mónica Espelt, Pablo Ballester
Jun 12, 2013·Journal of the American Chemical Society·Gautam R Desiraju
Sep 10, 2013·Journal of the American Chemical Society·Dong Sub KimJonathan L Sessler
Feb 6, 2014·Journal of the American Chemical Society·Louis AdriaenssensPablo Ballester
Jul 1, 2014·Accounts of Chemical Research·Sung Kuk Kim, Jonathan L Sessler
Feb 27, 2015·Chemical Reviews·Lei YouEric V Anslyn
Jun 20, 2015·Current Medicinal Chemistry·A M Mfuh, O V Larionov
Sep 22, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gemma AragayPablo Ballester
Jun 9, 2016·Chemical Communications : Chem Comm·Juhoon LeeJonathan L Sessler
Mar 24, 2018·Chemical Science·Albano GalánPablo Ballester
Sep 1, 2016·Chemical Science·Albano GalánPablo Ballester
Nov 30, 2018·Chemical Communications : Chem Comm·C A Gunawardana, C B Aakeröy
Dec 24, 2018·Chemical Society Reviews·Amit SharmaJong Seung Kim
Apr 19, 2019·Chemical Science·Cristian GozalvezAurelio Mateo-Alonso
Sep 24, 2019·Angewandte Chemie·Michael K Bellas, Adam J Matzger
Jan 21, 2020·Chemical Society Reviews·Sangshan PengJonathan L Sessler
Feb 12, 2020·Journal of the American Chemical Society·Andrés F SierraPablo Ballester

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography
X-ray
NMR
isothermal titration calorimetry

Software Mentioned

CAM

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.