A calorimetric titration study of the reaction of several organic ammonium cations with 18-crown-6 in methanol

Izatt, Reed M.; Lamb, John D.; Izatt, Neil E.; Rossiter, Bryant E.; Christensen, James J.; Haymore, Barry L.

doi:10.1021/ja00515a019

Cited by 119 publications

(66 citation statements)

References 8 publications

(11 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The complex stability depends on the number of H-bonds possible between host and guest [793], but also on the acidity of the ammonium ion. The more acidic an ammonium ion is, the stronger are the H-bonds with a particular donor site.…”

Section: Resultsmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

213

130

View full text Add to dashboard Cite

SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

show abstract

Section: Resultsmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

213

130

View full text Add to dashboard Cite

show abstract

“…Since the 1970s, various studies have been conducted on the complexation between the 18-crown-6 ether and a primary ammonium cation [24][25][26][27]. The crown ether is wellknown as an artificial receptor entrapping biologically important amino compounds due to the reasonably sized cavity for the inclusion of protonated amino groups (-NH 3 + ) as well as the tripodal arrangement of hydrogen bonds.…”

Section: Complexation Mechanismmentioning

confidence: 99%

Recognition of Lysine Residues on Protein Surfaces Using Calixarenes and its Application

Oshima¹,

Baba²,

Shimojo³

et al. 2007

CDDT

View full text Add to dashboard Cite

A macrocyclic calix[6]arene carboxylic acid derivative is found to extract lysine-rich protein cytochrome c from aqueous media into organic media through the complexation between the calixarene molecules and lysine residues on the surface of the protein. This article summarizes both the mechanism of protein extraction by the calixarene as well as the potential applications of the extraction process. The extraction process can be used for the purification of proteins through selective extraction and back-extraction under optimized conditions. On the other hand, the extracted protein exhibits enzymatic activity in organic media. The formation of a supramolecular complex by recognizing the residues on a protein surface can be construed as a novel recognition and/or modification method for biomacromolecules.

show abstract

“…In addition, cyclic polyethers have attracted interest as model substances for bio-systems (see above), separation techniques, chemical analysis or in relation to their use in synthetic methods in organic chemistry [7,8]. In the case of crown ethers, this is due to the fact that they can selectively form strong electrostatic complexes with a large variety of ligands in different solvents [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of mixtures containing oxaalkanes. 5. Ether+benzene, or +toluene systems

González

Fuenté

Cobos

2011

Fluid Phase Equilibria

View full text Add to dashboard Cite

A calorimetric titration study of the reaction of several organic ammonium cations with 18-crown-6 in methanol

Cited by 119 publications

References 8 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Recognition of Lysine Residues on Protein Surfaces Using Calixarenes and its Application

Thermodynamics of mixtures containing oxaalkanes. 5. Ether+benzene, or +toluene systems

Contact Info

Product

Resources

About