Interpretation of chromatographic retentions of simple solutes with an amylose-based sorbent using infrared spectroscopy and DFT modeling

Adsorption

Volumn 12, Issue 5-6, 2006, Pages 405-416

  Kasat, Rahul B ^a   Chin, Chim Y ^a,b   Thomson, Kendall T ^a   Franses, Elias I ^a   Wang, Nien Hwa Linda ^a  

^a PURDUE UNIVERSITY   (United States)

^b PureVision Technology Inc   (United States)

Author keywords

Amylose tris(3,5 dimethylphenylcarbamate); Capacity factors; Chiral separation; Dipole dipole interactions; Hydrogen bonding; Hydrophobic interactions

Indexed keywords

CAPACITY FACTORS; CHIRAL SEPARATION; HYDROPHOBIC INTERACTIONS; POLYMER FILMS; PYRIDINES; SOLUTES; TETRAHYDROFURAN;

ALCOHOLS; COMPUTER SIMULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BONDS; INFRARED SPECTROSCOPY; PROBABILITY DENSITY FUNCTION;

SORPTION;

EID: 33845383783     PISSN: 09295607     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10450-006-0568-7     Document Type: Article

References (29)

1. Agranat, I. et al., "Putting Chirality to Work: The Strategy of Chiral Switches," Nature Review Drug Discovery, 1(10), 753-768 (2002).
2. Andersson, M.P. and P. Uvdal, "New Scale Factors for Harmonic Vibrational Frequencies Using the B3LYP Density Functional Method with the Triple-ú Basis Set 6-311+G(d,p)," J. Phys. Chem. A, 109, 2937 (2005).
3. Armstrong, D.W. and W. Demond, "Cyclodextrin Bonded Phases for the Liquid-Chromatographic Separation of Optical, Geometrical, and Structural Isomers," J. Chromatogr. Sci., 22(9), 411-415 (1984).
4. Armstrong, D.W. et al., "Macrocyclic Antibiotics as a New Class of Chiral Selectors for Liquid-Chromatography," Anal., Chem., 66(9), 1473-1484 (1994).
5. Becke, A.D., J. "Density-Functional Thermochemistry. 3. The Role of Exact Exchange," Chem. Phys., 98, 5648 (1993).
6. Booth, T.D. and I.W. Wainer, "Investigation of the Enantioselective Separations of Alpha-Alkylarylcarboxylic Acids on an Amylose tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phase Using Quantitative Structure-Enantioselective Retention Relationships - Identification of a Conformationally Driven Chiral Recognition Mechanism," J. Chromatogr. A, 737(2), 157-169 (1996).
7. Caccamese, S. and G. Principato, "Separation of the Four Pairs of Enantiomers of Vincamine Alkaloids by Enantioselective High-Performance Liquid Chromatography," J. Chromatogr. A, 893(1), 47-54 (2000).
8. Chilmonczyk, Z. et al., "Enantioselective Separation of 1,4-disubstituted Piperazine Derivatives on Two Cellulose Chiralcel OD and OJ and one Amylose Chiralpak AD Chiral Selectors," Chirality, 11(10), 790-794 (1999).
9. Frisch, M.J.T., Gaussian 03. Wallingford CT (2004).
10. Goossens, J.F. et al., "Column Selection and Method Development for the Separation of Nucleoside Phosphotriester Diastereoisomers, New Potential Anti-Viral Drugs. Application to Cellular Extract Analysis," Biomed. Chromatogr., 19(6), 415-425 (2005).
11. Jadaud, P. and I.W. Wainer, "Stereochemical Recognition of Enantiomeric and Diastereomeric Dipeptides by High-Performance Liquid-Chromatography on a Chiral Stationary Phase Based Upon Immobilized Alpha-Chymotrypsin," J. Chromatogr., 476, 165-174 (1989).
12. Lammerhofer, M. and W. Lindner, "Quinine and Quinidine Derivatives as Chiral Selectors.1. Brush Type Chiral Stationary Phases for High-Performance Liquid Chromatography Based on Cinchonan Carbamates and their Application as Chiral Anion Exchangers," J. Chromatogr. A, 741(1), 33-48 (1996).
13. Lee K.B. et al., "Standing-Wave Design of a Simulated Moving Bed Under a Pressure Limit for Enantioseparation of Phenylpropanolamine," I & ERC, 44(9), 3249-3267 (2005).
14. Levitt, M. and M.F. Perutz, "Aromatic Rings Act as Hydrogen-Bond Acceptors," J. Mol. Biol., 201(4), (1988).
15. Meyer, E.A., et al., "Interactions with Aroamatic Rings in Chemical and Biological Recognition," Angew. Chem. Int. Ed., 42(11), 1210-1250 (2003).
16. Meyer, M. et al., "Density Functional Study of Guanine and Uracil Quartets and of Guanine Quartet/Metal Ion Complexes," J Comp. Chem., 22(1), 109 (2001).
17. Okamoto, Y. et al., "Chromatographic Resolution. 17. Useful Chiral Stationary Phases for Hplc-Amylose Tris(3,5-Dimethylphenylcarbamate) and Tris(3,5-Dichlorophenylcarbamate) Supported on Silica-Gel," Chem. Lett., (9), 1857-1860 (1987a).
18. Okamoto, Y. et al., "Chromatographic Chiral Resolution.14. Cellulose Tribenzoate Derivatives as Chiral Stationary Phases for High-Performance Liquid-Chromatography," J. Chromatogr., 389(1), 95-102 (1987b).
19. Okamoto, Y. and E. Yashima, "Polysaccharide Derivatives for Chromatographic Separation of Enantiomers," Angew. Chem. Int. Ed. Engl., 37, 1020-1043 (1998).
20. Pimentel, G.C. and A.L. McClellan, The Hydrogen Bond, San Francisco, W.H. Freeman, 1960.
21. Pirkle, W.H. et al., "Broad-Spectrum Resolution of Optical Isomers Using Chiral High-Performance Liquid-Chromatographic Bonded Phases," J. Chromatogr., 192(1), 143-158 (1980).
22. Scheiner, S. Hydrogen Bonding: A Theoretical Perspective, New York, Oxford University Press, 1997.
23. Simon, S. et al., "How does Basis Set Superposition Error Change the Potential Surfaces for Hydrogen Bonded Dimers?," J. Chem. Phys., 105(24), 11024-11031 (1996).
24. Snyder, L.R. et al., Practical HPLC Method Development, Wiley-Interscience, 1997.
25. Wang, T. et al., "Enantiomeric Separation of Some Pharmaceutical Intermediates and Reversal of Elution Orders by High-Performance Liquid Chromatography Using Cellulose and Amylose tris(3,5-dimethylphenylcarbamate) Derivatives as Stationary Phases," J. Chromatogr. A, 902(2), 345-355 (2000).
26. Wenslow, R. and T. Wang, "Solid-State NMR Characterization of Amylose Tris (3,5-dimethylphenylcarbamate) Chiral Stationary-Phase Structure as a Function of Mobile-Phase Composition," Anal. Chem., 73, 4190-4195 (2001).
27. Yamamoto, C. et al., "Structural Analysis of Amylose Tris(3,5-dimethylphenylcarbamate) by NMR Relevant to its Chiral Recognition Mechanism in HPLC," J. Am. Chem. Soc., 124(42), 12583-12589 (2002).
28. Yashima, E., "Poly saccharide-Based Chiral Stationary Phases for High-Performance Liquid Chromatographic Enantioseparation," J. Chromatogr. A, 906(1-2), 105-125 (2001).
29. Yashima, E. and Y. Okamoto, "Optically Active Polymers for Chiral Separations," Bull. Chem. Soc. Jpn., 77(2), 227-257 (2004).