Solvation of the Whelk-O1 chiral stationary phase: A molecular dynamics study

Journal of Chromatography A

Volumn 1131, Issue 1-2, 2006, Pages 110-129

  Zhao, Chunfeng ^a   Cann, N M ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Chiral stationary Phase; HPLC; Molecular dynamics simulation; Normal phase; Reversed phase; Supercritical; Whelk O1

Indexed keywords

CHIRAL STATIONARY PHASE; MOLECULAR DYNAMICS SIMULATION; REVERSED-PHASE; SOLVENT COMPOSITION;

COMPUTER SIMULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BONDS; PROBABILITY DENSITY FUNCTION; SOLVENTS;

MOLECULAR DYNAMICS;

2 PROPANOL; CARBON DIOXIDE; HEXANE; METHANOL; SOLVENT; WATER;

ANALYTIC METHOD; ARTICLE; CALCULATION; CHEMICAL COMPOSITION; CHIRAL CHROMATOGRAPHY; CHIRALITY; DENSITY FUNCTIONAL THEORY; EXTRACTION; HYDROGEN BOND; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOLVATION; SUPERCRITICAL FLUID;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMPUTER SIMULATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SOLVENTS; STEREOISOMERISM;

EID: 33749317497     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chroma.2006.07.085     Document Type: Article

References (74)

1. Ward T.J., and Hamburg D.M. Anal. Chem. 76 (2004) 4635
2. Lipkowitz K.B. J. Chromatogr. A 666 (1994) 493
3. Pirkle W.H., Welch C.J., and Lam B. J. Org. Chem. 57 (1992) 3854
4. Pirkle W.H., and Welch C.J. J. Liquid Chromatogr. 15 (1992) 1947
5. Wolf C., Pranatharthiharan L., and Volpe E.C. J. Org. Chem. 68 (2003) 3287
6. Liu D., Wang P., Zhou W., Gu X., Chen Z., and Zhou Z. Anal. Chim. Acta 555 (2006) 210
7. Pirkle W.H., and Welch C.J. Tetrahedron: Asymm. 5 (1994) 777
8. Pirkle W.H., and Gan K.Z. J. Chromatogr. A 790 (1997) 65
9. Pirkle W.H., Brice L.J., and Terfloth G.J. J. Chromatogr. A 753 (1996) 109
10. Oswald P., Desmet K., Sandra P., Krupčík J., Májek P., and Armstrong D.W. J. Chromatogr. B 779 (2002) 283
11. Kraml C.M., Zhou D., Byrne N., and McConnell O. J. Chromatogr. A 1100 (2005) 108
12. Dungelova J., Lehotay J., Cizmarik J., and Armstrong D.W. J. Liquid Chromatogr. Relat. Tech. 26 (2003) 2331
13. Rio A.D., Hayes J.M., Stein M., Piras P., and Roussel C. Chirality 16 (2004) S1
14. Roussel C., Rio A.D., Pierrot-Sanders J., Piras P., and Vanthuyne N. J. Chromatogr. A 1037 (2004) 311
15. Pirkle W.H., and Welch C.J. J. Chromatogr. A 683 (1994) 347
16. Hyun M.H., Ryoo J.J., and Pirkle W.H. J. Chromatogr. A 886 (2000) 47
17. Job G.E., Shvets A., Pirkle W.H., Kuwahara S., Kosaka M., Kasai Y., Taji H., Fujita K., Watanabe M., and Harada N. J. Chromatogr. A 1055 (2004) 41
18. Katte S.J., and Beck T.L. J. Phys. Chem. 97 (1993) 5727
19. Slusher J.T., and Mountain R.D. J. Phys. Chem. B 103 (1999) 1354
20. Chemng C.Y., Chem T.L., and Wang B.C. J. Mol. Struct. (Theochem) 577 (2002) 81
21. Zhang L., Sun L., Siepmann J.I., and Schure M.R. J. Chromatogr. A 1079 (2005) 127
22. Nita S., Cann N.M., and Horton J.H. J. Phys. Chem. B 108 (2004) 3512
23. Nita S., Cann N.M., and Horton J.H. J. Phys. Chem. B 110 (2006) 9511
24. T.J. Szczerba, Regis Technologies, Inc., personal communication.
25. Nawrocki J. J. Chromatogr. A 779 (1997) 29
26. Lipkowitz K.B. Acc. Chem. Res. 33 (2000) 555
27. Lipkowitz K.B. J. Chromatogr. A 906 (2001) 417
28. Lipkowitz K.B., Pearl G., Coner B., and Peterson M.A. J. Am. Chem. Soc. 119 (1997) 600
29. Pirkle W.H., Gan K.Z., and Brice L.J. Tetrahedron: Asymm. 7 (1996) 2813
30. Altomare C., Carotti A., Cellamare S., Fanelli F., Gasparrini F., Villani C., Carrupt P.A., and Testa B. Chirality 5 (1993) 527
31. Suzuki T., Timofei S., Iuoras B.E., Uray G., Verdino P., and Fabian W.M.F. J. Chromatogr. A 922 (2001) 13
32. Fabian W.M.F., Stampfer W., Mazur M., and Uray G. Chirality 15 (2003) 271
33. Rio A.D., Piras P., and Roussel C. Chirality 17 (2005) S74
34. Wolf C., and Pirkle W.H. Tetrahedron 58 (2002) 3597
35. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M. C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, Gaussian 03, Revision C.02, 2004.
36. Becke A.D. J. Chem. Phys. 98 (1993) 564
37. Clark T., Chandrasekhar J., Spitznagel G.W., and Schleyer P.v.R. J. Comp. Chem. 4 (1983) 294
38. Frisch M.J., Pople J.A., and Binkley J.S. J. Chem. Phys. 80 (1984) 3265
39. Andersen H.C. J. Comput. Phys. 52 (1983) 24
40. Lopes P.E.M., Murashov V., Tazi M., Demchuk E., and MacKerell Jr. A.D. J. Phys. Chem. B 110 (2006) 2782
41. Stubbs J.M., Potoff J.J., and IIja Siepmann J. J. Phys. Chem. B 108 (2004) 17596
42. Cornell W.D., Cieplak P., Bayly C.I., Gould I.R., Merz Jr. K.M., Ferguson D.M., Spellmeyer D.C., Fox T., Caldwell J.W., and Kollman P.A. J. Am. Chem. Soc. 117 (1995) 5179
43. Ryckaert J.P., and Bellemans A. Far. Disc. Chem. Soc. 66 (1978) 95
44. Jorgensen W.L., Madura J.D., and Swenson C.J. J. Am. Chem. Soc. 106 (1984) 6638
45. Jorgensen W.L., and Tirado-Rives J. J. Am. Chem. Soc. 110 (1988) 1657
46. E04USF, The NAG Fortran Library, Mark 21, Numerical Algorithms Group, Oxford, UK, 2005.
47. Breneman C.M., and Wiberg K.B. J. Comp. Chem. 11 (1990) 361
48. Lorentz H.A. Annalen Phys. 2 (1981) 127
49. Berthelot D.C. (r) Hebd. Séanc. Acad. Sci., Paris 126 (1898) 1703
50. Price M.L.P., Ostrovsky D., and Jorgensen W.L. J. Comput. Chem. 22 (2001) 1340
51. Briggs J.M., Matsui T., and Jorgensen W.L. J. Comput. Chem. 11 (1990) 958
52. Chen B., Potoff J.J., and Siepmann J.I. J. Phys. Chem. B 105 (2001) 3093
53. Levitt M., Hirshberg M., Sharon R., Laidig K.E., and Daggett V. J. Phys. Chem. B 101 (1997) 5051
54. Harris J.G., and Yung K.H. J. Phys. Chem. 99 (1995) 12021
55. Ewald P. Ann. Phys. Lpz. 64 (1921) 253
56. Yeh I.C., and Berkowitz M.L. J. Chem. Phys. 11 (1990) 3155
57. Smith B.D., and Srivastava R. Thermodynmic Data for Pure Compounds (1986), Elsevier, Amsterdam
58. Goldfarb D.L., Fernández D.P., and Corti H.R. Fluid Phase Equilibria 158-160 (1999) 1011
59. Wensink E.J.W., Hoffmann A.C., van Maaren P.J., and van der Spoel D. J. Chem. Phys. 119 (2003) 7308
60. Nosé S. J. Chem. Phys. 81 (1984) 511
61. Hoover W.G. Phys. Rev. A 31 (1985) 1695
62. Martyna G.J., Tobias D.J., and Klein M.L. J. Chem. Phys. 101 (1994) 4177
63. E. Cressman, B. Das, J. Dunford, R. Ghenea, Y. Huh, S. Nita, I. Paci, S. Wang, C. Zhao, N.M. Cann, unpublished.
64. Levitt M., and Sharon R. Proc. Natl. Acad. Sci. 85 (1988) 7557
65. Luzar A., and Chandler D. Phys. Rev. Lett. 76 (1996) 928
66. Phinney K.W. Anal. Bioanal. Chem. 382 (2005) 639
67. Eckert C.A., Knutson B.L., and Debenedetti P.G. Nature 383 (1996) 313
68. D'Angelo M., Onori G., and Santucci A. J. Chem. Phys. 100 (1994) 3107
69. Dixit S., Crain J., Poon W.C.K., Finney J.L., and Soper A.K. Nature 416 (2002) 829
70. Yamaguchi T., Takamuku T., and Soper A.K. J. Neutr. Res. 13 (2005) 129
71. Duffy E.M., Kowalczyk P.J., and Jorgensen W.L. J. Am. Chem. Soc. 115 (1993) 9271
72. Price M.L.P., Ostrovsky D., and Jorgensen W.L. J. Comput. Chem. 22 (2001) 1340
73. J.M. Briggs, T.M., W.L. Jorgensen, J. Comput. Chem. 11 (1990) 958.
74. Jorgenson W.L. J. Phys. Chem. 90 (1896) 1276