Free Energy Perturbation and Molecular Dynamics Simulation Studies on the Enantiomeric Discrimination of Amines by Dimethyldiketopyridino-18-Crown-6

Supramolecular Chemistry

Volumn 12, Issue 3, 2000, Pages 255-272

  Lee, One Sun ^a   Hwang, Sungu ^a   Chung, Doo Soo ^a  

^a Seoul National University   (South Korea)

Author keywords

Chiral separation; Free Energy Perturbation (FEP); Gas phase; Molecular Dynamics (MD); Pyridino 18 crown 6

Indexed keywords

EID: 0034560623     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610270008029448     Document Type: Article

References (35)

1. Janoschek, R. Chirality: From Weak Bosons to α-Helix; Springer-Verlag: Berlin, 1991.
2. Thall, E. J. Chem. Educ. 1996, 73, 481-484.
3. Nielen, M.W.F. Anal. Chem. 1993, 65, 885-893.
4. Terabe, S.; Shibata, M.; Miyashita, Y. J. Chromatogr. 1989, 480, 403-411.
5. Kyba, E.P.; Timko, J.M.; Kaplan, L.J.; Jong, F.D.; Gokel, G.W.; Cram, D.J. J. Am. Chem. Soc. 1978, 100, 4555-4568.
6. Sousa, L.R.; Sogah, G.D.Y.; Hoffman, D.H.; Cram, D.J. J. Am. Chem. Soc. 1978, 100, 4569-4576.
7. Cram, D.J.; Cram, J.M. Science 1974, 183, 803-809.
8. Izatt, R.M.; Bradshaw, J.S.; Nielsen, S.A.; Lamd, J.D.; Christensen, J.J.; Sen, D. Chem. Rev. 1985, 85, 271-339.
9. Inoue, Y.; Gokel, G.W. Cation Binding by Macrocycles: Complexation of Cationic Species by Crown Ether, Marcel Dekker, Inc.: New York, 1990.
10. Atwood, J.L. Inclusion Phenomena and Molecular Recognition; Plenum Press: New York, 1990.
11. Kuhn, R.; Erni, F.; Bereuter, T.; Häusler, J. Anal. Chem. 1992, 64, 2815-2820.
12. Zhang, X.X.; Izatt, R.M.; Zhu, C.Y.; Bradshaw, J.S. Supramol. Chem. 1996, 6, 267-274.
13. Dearden, D.V.; Dejsupa, C.; Liang, Y.; Bradshaw, J.S.; Izatt R.M. J. Am. Chem. Soc. 1997, 119, 353-359.
14. Bradshaw, J.S.; Huszthy, P.; Redd, J.T.; Zhang, X.X.; Wang, T.; Hathaway, J.K.; Young, J.; Izatt, R.M. Pure Appl. Chem. 1995, 67, 691-695.
15. Wang, T.; Bradshaw, J.S.; Huszthy, P.; Izatt, R.M. Supramol. Chem. 1996, 6, 251-255.
16. Bradshaw, J.S.; Huszthy, P.; McDaniel, C.W.; Zhu, C.Y.; Dalley, N.K.; Izatt, R. M.; Lifson, S. J. Org. Chem. 1990, 55, 3129-3137.
17. Kollman, P. Chem. Rev. 1993, 93, 2395-2417.
18. Allen, M.P.; Tildesley, D.J. Computer Simulation of Liquids; Clarendon Press: Oxford, 1987.
19. Davidson, R.B.; Dalley, N.K.; Izatt, R.M.; Bradshaw, J.S.; Campana, C.F. Isr. J. Chem. 1985, 25, 33-38.
20. Izatt, R.M.; Zhu, C.Y.; Dalley, N.K.; Curtis, J.C.; Kou, X.; Bradshaw, J.S. J. Phys. Org. Chem. 1992, 5, 656-662.
21. McCammon, J.A. Science 1987, 238, 486-491.
22. Armstrong, D.W.; Ward, T.J.; Armstrong, R.D.; Beesley, T.E. Science 1986, 23, 1132-1135.
23. Pirkle, W.H.; Pochapsky, T.C. Chem. Rev. 1989, 89, 347-362.
24. Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440-467.
25. Guarnieri, F.; Still, W.C. J. Comput. Chem. 1994, 15, 1302-1310.
26. Zwanzig, R.W. J. Chem. Phys. 1954, 22, 1420-1426.
27. Kirkwood, J.G. J. Chem. Phys. 1935, 3, 300-313.
28. Hwang, S.; Lee, K.H.; Ryu, G.H.; Jang, Y.H.; Lee, S.B.; Lee, W.Y.; Hong, J.-I.; Chung, D.S. in press (J. Org. Chem.).
29. Wang, J.; Kollman, P.A. J. Am. Chem. Soc. 1998, 120, 11106-11114.
30. Jorgensen, W.L.; Ravimohan, C. J. Chem. Phys. 1985, 83, 3050-3054.
31. Aerts, J. J. Comput. Chem. 1995, 16, 914-922.
32. Davidson, R.B.; Bradshaw, J.S.; Jones, B.A.; Dalley, N.K.; Christensen, J.J.; Izatt, R.M.; Morin, F.G.; Grant, D.M. J. Org. Chem. 1984, 49, 353-357.
33. Lee, O.-S.; Hwang, S.; Chung, D.S. Free Energy Perturbation Study on Enantioselectivity of Crown Ethers. Asianalysis IV, Fukuoka, Japan, May 21-23, 1997; Japan Society for Analytical Chemistry: 1997; 2C10, 70.
34. Lipkowitz, K.B.; Demeter, D.A.; Zegarra, R.; Larter, R.; Darden, T. J. Am. Chem. Soc. 1988, 110, 3446-3452.
35. Lipkowitz, K.B.; Demeter, D.A.; Parish, C.A.; Darden, T. Anal. Chem. 1987, 59, 1731-1733.