Related Experiment Video
Updated: Mar 7, 2026
10:10
Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study
Published on: August 15, 2016
10.8K
Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds
Cira Mollings Puentes1, Thomas J Wenzel1
1Department of Chemistry, Bates College, Lewiston, Maine 04240 USA.
Beilstein Journal of Organic Chemistry
|February 10, 2017
Summary
Phosphated cyclodextrins serve as effective chiral NMR solvating agents for cationic substrates. These compounds, particularly those with higher substitution, show enhanced enantiomeric differentiation compared to previous agents.
Area of Science:
- Analytical Chemistry
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Chiral recognition is crucial in chemistry and drug development.
- Water-soluble chiral solvating agents are needed for NMR analysis of cationic species.
- Cyclodextrins are versatile hosts with tunable properties.
Purpose of the Study:
- To evaluate phosphated cyclodextrins as chiral NMR solvating agents for cationic substrates.
- To investigate the effect of substitution degree on chiral differentiation.
- To explore the use of lanthanide ions to enhance NMR spectral analysis.
Main Methods:
- Synthesis and characterization of phosphated α-, β-, and γ-cyclodextrins with varying degrees of substitution (2-6 and 6-10).
- Nuclear Magnetic Resonance (NMR) spectroscopy of 33 water-soluble cationic substrates.
- Addition of paramagnetic lanthanide ions (Pr(III), Yb(III)) to assess enhanced chiral differentiation.
Main Results:
- Phosphated cyclodextrins effectively differentiate enantiomers of cationic substrates in NMR spectra.
- Higher degrees of substitution (6-10) generally led to greater enantiomeric differentiation.
- Lanthanide ions showed potential for further enhancing chiral discrimination.
- Performance was compared to anionic carboxymethylated cyclodextrins, with phosphated versions often showing superior results.
Conclusions:
- Phosphated cyclodextrins are valuable, water-soluble chiral NMR solvating agents for cationic compounds.
- The degree of phosphation significantly influences their efficacy in chiral recognition.
- These agents offer an improved alternative to existing methods for enantiomeric analysis.
More Related Videos
Related Concept Videos
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
7.2K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.2K
01:17Ion Exchange
1.4K
Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
1.4K
04:01Factors Affecting Solubility
37.7K
Compared with pure water, the solubility of an ionic compound is less in aqueous solutions containing a common ion (one also produced by dissolution of the ionic compound). This is an example of a phenomenon known as the common ion effect, which is a consequence of the law of mass action that may be explained using Le Chȃtelier’s principle. Consider the dissolution of silver iodide:
37.7K
02:55Solubility of Ionic Compounds
68.9K
Solubility is the measure of the maximum amount of solute that can be dissolved in a given quantity of solvent at a given temperature and pressure. Solubility is usually measured in molarity (M) or moles per liter (mol/L). A compound is termed soluble if it dissolves in water.
68.9K
02:30Racemic Mixtures and the Resolution of Enantiomers
22.3K
A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
22.3K
03:00Solubility
21.7K
Solution, Solubility, and Solubility Equilibrium
A solution is a homogeneous mixture composed of a solvent, the major component, and a solute, the minor component. The physical state of a solution—solid, liquid, or gas—is typically the same as that of the solvent. Solute concentrations are often described with qualitative terms such as dilute (of relatively low concentration) and concentrated (of relatively high concentration).
In a solution, the solute particles (molecules,...
A solution is a homogeneous mixture composed of a solvent, the major component, and a solute, the minor component. The physical state of a solution—solid, liquid, or gas—is typically the same as that of the solvent. Solute concentrations are often described with qualitative terms such as dilute (of relatively low concentration) and concentrated (of relatively high concentration).
In a solution, the solute particles (molecules,...
21.7K