Related Experiment Video
Updated: Jul 19, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Structure-selective recognition by voltammetry: enantiomeric determination of amines using azophenolic crowns in
Kyungmin Chun1, Tae Hyun Kim, One-Sun Lee
1Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
Abstract:
The enantiomeric recognition of amines by voltammetry using electroactive macrocyclic molecules, nitroazophenolic crown ethers, is reported. The oxidation potential of the nitroazophenol moiety in nitroazophenols with 18-crown-6 sensitively depends on the structure of alkyl amines. Based on this phenomenon, enantiomeric amines and even the quantitative assay of the R/S ratio in enantiomeric mixtures can be selectively recognized by using 18-crown-6 azophenol (3-H) with chiral centers. In the case of phenylglycinol, the association constants (K) of 3-H for the R and S forms have an R/S value of 3.5. The peak potential of the R form in square-wave voltammograms reproducibly differs from that of the S form by 32 mV, within which the peak potential linearly varies with the enantiomeric ratio. Free energy perturbation and molecular dynamics simulation provide deeper understanding of the enantiomeric recognition in this system. The theoretical analysis indicates that the free energy difference between diastereomeric complexes agrees well with the experimental results, and the pi-pi or charge-charge interaction plays a key role in enantiomeric recognition.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Structure of Amines
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Basicity of Heterocyclic Aromatic Amines

