Cooperative NH⋯O and CH⋯O interactions for sulfate encapsulation in a thiophene-based macrocycle.

Tetrahedron Letters
Musabbir A SaeedMd Alamgir Hossain

Abstract

A thiophene-based macrocycle containing four secondary and two tertiary amines has been synthesized and its binding affinity has been investigated toward sulfate anion in solution and solid states. Structural analysis of the sulfate salt suggests that the ligand in its hexaprotonated form, is capable of encapsulating one sulfate within the cavity through cooperative NH⋯O and CH⋯O interactions. As investigated by (1)HNMR titrations, the lignad forms a 1:1 complex with sulfate in water at pH 2.1, showing a binding constant (K) of 3200 M(-1). The formation of the complex has been further confirmed by ESI-MS, indicating that the complex can exist in solution with a considerable stability.

References

Apr 1, 1973·The Journal of Cell Biology·R W Young
Aug 18, 2005·Accounts of Chemical Research·Kristin Bowman-James
Jan 27, 2009·Chemical Society Reviews·Claudia Caltagirone, Philip A Gale
Jan 13, 2010·Chemical Communications : Chem Comm·Musabbir A SaeedMd Alamgir Hossain
May 25, 2010·Crystal Growth & Design·Md Alamgir HossainDon Gibson

❮ Previous
Next ❯

Citations

Jul 24, 2010·Chemical Communications : Chem Comm·John S MendyMd Alamgir Hossain
Feb 21, 2014·Organic & Biomolecular Chemistry·M Mhahabubur RhamanM Alamgir Hossain
Nov 15, 2011·Chemical Society Reviews·Marco WenzelPhilip A Gale
Feb 22, 2017·Comments on Modern Chemistry. Part A, Comments on Inorganic Chemistry : a Journal of Critical Discussion of the Current Literature·Syed A HaqueMd Alamgir Hossain

❮ 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.