Preparation of a new chiral pyridino-crown ether-based stationary phase for enantioseparation of racemic primary organic ammonium salts

Industrial and Engineering Chemistry Research

Volumn 39, Issue 10, 2000, Pages 3576-3581

  Horvath, G ^a   Huszthy, P ^b   Szarvas, S ^c   Szokan, G ^c   Redd, J T ^d   Bradshaw, J S ^e   Izatt, R M ^e  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^c EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^d SOUTHERN UTAH UNIVERSITY   (United States)

^e Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; CHEMICAL BONDS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SALTS; SEPARATION; SILANES; SILICA GEL;

AMINOPROPYLTRIMETHOXYSILANE; ENANTIOSEPARATION; LIGANDS; NAPHTHYLETHYLAMMONIUM PERCHLORATE; PHENYLETHYLAMMONIUM PERCHLORATE;

CROWN ETHERS;

1 PHENYLETHYLAMMONIUM PERCHLORATE; 3 AMINOPROPYLTRIMETHYLSILANE; ALPHA (1 NAPHTHYL)ETHYLAMMONIUM PERCHLORATE; AMIDE; AMMONIA; CROWN ETHER; PYRIDINE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; X RAY CRYSTALLOGRAPHY;

EID: 0034306201     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie000272a     Document Type: Article

References (45)

1. Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors
2. Chiral Recognition in Molecular Complexing
3. The Design of Molecular Hosts, Guest, and Their Complexes
4. Practical Synthesis of a Highly Enantioselective Receptor For Peptides
5. Synthetic Chiral Receptor Molecules From Natural Products
6. Novel Monoaza- and Diazacrown Ethers Incorporating Sugar Units and Their Extraction Ability Towards Picrate Salts
7. Chiral Diaza-18-Crown-6 Derivatives
8. Enantiomeric Recognition of Organic Ammonium Salts by Chiral Crown Ethers Based on the Pyridino-18-Crown-6 Structure
9. The Preparation of New Chiral Diphenyl-Substituted Macrocyclic Polyether-Diester Compounds and Their Enantiomeric Recognition of Chiral Organic Ammonium Salts
10. 1H NMR and the Empirical Force Field Techniques
11. Recognition by Symmetrically Substituted Chiral Diphenyl and Di-t-butyl and Asymmetrically Substituted Chiral Dimethylpyridino-18-Crown-6 Ligands of the Enantiomers of Various Organic Ammonium Perchlorates
12. New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza- and Azapryidino-18-Crown-6 Ligands
13. Enantiomeric Recognition and Separation of Chiral Organic Ammonium Salts by Chiral Pyridino-18-crown-6 Ligands
14. Enantiomeric Separation of Chiral α-(1-Naphthyl)ethylammonium Perchlorates by Silica Gel-Bound Chiral Pyridino-18-Crown-6 Ligands
15. New Pyridino-18-Crown-6 Ligands Containing Two Methyl, Two tert-Butyl or Two Alkyl Substituents on Chiral Positions next to the Pyridine Ring
16. Enantioseparation of Racemic Organic Ammonium Perchlorates by Silica Gel-Bound Optically Active Di-tert-butylpyridino-18-crown-6 Ligands
17. Enantiomerically Pure Chiral Pyridino-Crown Ethers: Synthesis and Enantioselectivity Toward the Enantiomers of α-(1-Naphthyl)ethylammoninm Perchlorate
18. Factors Influencing Enantiomeric Recognition of Primary Alkylammonium Salts by Pyridino-18-Crown-6 Type Ligands
19. Enantiomeric Recognition of Chiral Ammonium Salts by Chrial Pyridino- and Pyrimidino-18-Crown-6 Ligands
20. Enantiomeric Recognition of Chiral Organic Ammonium Guests by Chiral Pyridino-18-Crown-6 Type Ligands in Alcohol/Dichloroethane Solvent Mixtures
21. 1H NMR Method for Determining Log K and ΔH Values for Crown Ether Alkylammonium Cation Complexation
22. Chiral Host-Guest Recognition in an Ion-Molecule Reaction
23. Chiral Recognition Via Host-Guest Interactions Detected by Fast-Atom Bombardment Mass Spectrometry: Principles and Limitations
24. Characterization of Chiral Host-Guest Complexation in Fast Atom Bombardment Mass Spectrometry
25. Structure and Conformation of Pyridino- and Diesterpyridino-18-Crown-6 Complexes with Primary Ammonium Salts in Solution and Crystalline States
26. A Thermodynamic and Structural Study of the Interactions of Pyridino-and Diesterpyridino-18-Crown-6 Ligands With Some Primary Organic Ammonium Cations
27. Conformational Analysis of (S, S)-Dimethyldiketopyridino-18-Crown-6
28. Molecular Recognition as Shown by the Solvent Extraction of (R)- and (S)-[α-(1-Naphthyl)ethyl]ammonium Picrate or Orange 2 by Chiral Pyridino-Crown Ethers
29. A Structural Analysis of the Complexes of (S, S)-Dimethylpyridino-18-Crown-6 with (R) and (S)-[α-(1-Naphthyl)-ethyl]ammonium Perchlorate by NMR Techniques and Molecular Modeling
30. Enantiomeric Recognition of Aralkyl Ammonium Salts by Chiral Pyridino-18-Crown-6 Ligands: Use of Circular Dichromism Spectroscoxy
31. CD-Monitored Enantiomeric Discrimination of Organic Ammonium Salts By Chiral Pyridino Macrocycles
32. Enantiomer Selectivity of Ion-Selective Electrodes Based on a Chiral Crown Ether Ionophore
33. Enantiomeric Recognition by Chiral Pyridino-18-Crown-6 Ligands for α-(1-Naphthyl)ethylammonium Perchlorate. The Affect of Alkyl Substituents on the Macrocycle Ring
34. Considerations of Chiral Recognition Relevant to the Liquid Chromatography Separation of Enantiomers
35. Empirical Procedure That Uses Molecular Structure to Predict Enantioselectivity of Chiral Stationary Phases
36. Host-Guest Complexation. 12. Total Optical Resolution of Amine and Amino Ester Salts By Chromatography
37. Host-Guest Complexation. 14. Host Covalently Bound to Polystyrene Resin for Chromatographic Resolution of Enantiomers of Amino Acid and Ester Salts
38. Chromatographic Enantioseparation of Racemic α-(1-Naphthyl)ethylammonium Perchlorate by a Merrifield Resin-Bound Enantiomerically Pure Chiral Dimethylpyridino-18-Crown-6 Ligand
39. Uber Die Synthesis von Acetessigester-[1-14C] und α,β-Diketobuttersaureester-[1-14C]