Molecular modeling of chiral-modified zeolite HY employed in enantioselective separation

Chirality

Volumn 19, Issue 6, 2007, Pages 508-513

  Jirapongphan, Siricharn S ^a   Warzywoda, Juliusz ^a   Budil, David E ^b   Sacco Jr , Albert ^a,b  

^a Northeastern University   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

Author keywords

Chiral discrimination; Chiral stationary phase; Enantioseparation; GCMC simulation; Molecular dynamics; Supercage based docking; Zeolite HY

Indexed keywords

BENZOIN; UNCLASSIFIED DRUG; ZEOLITE; ZEOLITE HY;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; MOLECULAR MODEL; MONTE CARLO METHOD; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SIMULATION;

COMPUTER SIMULATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MODELS, CHEMICAL; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MONTE CARLO METHOD; STEREOISOMERISM; ZEOLITES;

EID: 34250176136     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20408     Document Type: Article

References (25)

1. Thayer AM. Trial separations. Chem Eng News 2005;83:49-53.
2. Aboul-Enein HY, Ali I. Chiral separations by liquid chromatography and related technologies. New York: Marcel Dekker; 2003. 361 p.
3. Lipkowitz KB, Demeter DA, Zegarra R, Larter R, Darden T. A protocol for determining enantioselective binding of chiral analytes on chiral chromatographic surfaces. J Am Chem Soc 1988;110:3446-3452.
4. Lipkowitz KB, Baker B, Zegarra R. Theoretical studies in molecular recognition: enantioselectivity in chiral chromatography. J Comput Chem 1989;10:718-732.
5. Edge AM, Heaton DM, Bartle KD, Clifford AA, Myers P. A computational study of the chromatographic separation of racemic mixtures. Chromatographia 1995;41:161-166.
6. Del Rio A, Hayes JM, Stein M, Piras P, Roussel C. Theoretical reassessment of whelk-O1 as an enantioselective receptor for 1-(4-halogeno-phenyl)-1-ethylamine derivatives. Chirality 2004;16:S1-S11.
7. Still MG, Rogers LB. Molecular modelling of structural changes which affect chromatographic selectivity in chiral separations. Talanta 1989;36:35-48.
8. Davankov VA. The nature of chiral recognition: is it a three-point interaction? Chirality 1997;9:99-102.
9. Davankov VA, Meyer VR, Rais M. A vivid model illustrating chiral recognition induced by achiral structures. Chirality 1990;2:208-210.
10. Karahan O. Chiral separations using zeolite beta. Boston: Northeastern University; 2003. 126 p.
11. Manning MP, Warzywoda J, Karahan O, Sacco A Jr. Enantioselective adsorption of hydrobenzoin on zeolite beta. Stud Surf Sci Catal 2004;154A:1957-1960.
12. Jirapongphan SS, Warzywoda J, Budil DE, Sacco A Jr. Role of sorbate in determination of preferential adsorption sites in zeolite HY: A theoretical study. Micropor Mesopor Mater (in press).
13. Sun H. COMPASS: an ab initio force-field optimized for condensed-phase applications - overview with details on alkane and benzene compounds. J Phys Chem B 1998;102:7338-7364.
14. Jirapongphan SS, Warzywoda J, Budil DE, Sacco A Jr. Simulation of benzene adsorption in zeolite HY using supercage-based docking. Micropor Mesopor Mater 2006;94:358-363.
15. Materials Studio software package by Accelrys. Available from: 〈www.accelrys.com〉.
16. Ewald PP. Evaluation of optical and electrostatic lattice potentials. Ann Phys (Leipzig) 1921;64:253-287.
17. Leach AR. Molecular modelling principles and applications. England: Prentice Hall; 2001. 744 p.
18. Auerbach SM, Jousse F, Vercauteren DP. Dynamics of sorbed molecules in zeolites. In: Callow CRA, van Santen RA, Smit B, editors. Computer modelling of microporous and mesoporous materials. Amsterdam: Elsevier; 2004. pp 49-108.
19. Jousse F, Auerbach SM, Vercauteren DP. Adsorption sites and diffusion rates of benzene in HY zeolite by force field based simulations. J Phys Chem B 2000;104:2360-2370.
20. 2H NMR and molecular dynamics. J Phys Chem 1993;97:11776-11780.
21. Schuring D, Jansen APJ, van Santen RA. Concentration and chain-length dependence of the diffusivity of alkalies in zeolites studied with MD simulations. J Phys Chem B 2000;104:941-948.
22. Honeycutt JD. A general simulation method for computing conformational properties of single polymer chains. Comput Theor Polym Sci 1998;8:1-8.
23. Barthomeuf D, Ha B-H. Adsorption of benzene and cyclohexane on faujasite-type zeolites part 1 thermodynamic properties at low coverage. J Chem Soc Faraday Trans 1 1973;69:2147-2157.
24. Aerts J. An improved molecular modeling method for the prediction of enantioselectivity. J Comput Chem 1995;16:914-922.
25. Still MG, Rogers LB. Effects of computational variations for determining binding energies of diastereomeric complexes when using MM2. J Comput Chem 1990;11:242-248.