Explanation of where and how enantioselective binding takes place on permethylated β-cyclodextrin, a chiral stationary phase used in gas chromatography

Journal of the American Chemical Society

Volumn 119, Issue 3, 1997, Pages 600-610

  Lipkowitz, Kenny B ^a   Pearl, Greg ^a   Coner, Bob ^a   Peterson, Michael A ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE;

ARTICLE; COMPLEX FORMATION; COMPUTER SIMULATION; ENANTIOMER; GAS CHROMATOGRAPHY; MOLECULAR DYNAMICS; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0031028851     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963076x     Document Type: Article

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44. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
45. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
46. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
47. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
48. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
49. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
50. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
51. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
52. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
53. Pertinent discussions can be found throughout ref 8; for additional reviews concerning applications of cyclodextrins, see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353 (c) Beesley, T. E. Am. Laboratory 1985, May, 78. (d) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Laboratory, 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, September, 646. (j) Husain, N.; Warner, I. M. Am. Laboratory 1993, October, 80.
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55. For reviews see: (a) Vespalec, R.; Bocek, P. Electrophoresis 1994, 15, 755. (b) Nishi, H.; Terabe, S. J. Chromatogr. A 1995, 694, 246. (c) Guttman, A.; Brunet, S.; Cooke, N. LC-GC 1996, January, 14, 32.
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130. Several papers concerning MD simulations of enantiomers binding to cyclodextrins but not predicting retention times exist; see (a) Lipkowitz, K. B.; Raghothama, S.; Yang, J. J. Am. Chem. Soc. 1992, 114, 1554. (b) Eliseev, A. V.; Iacobucci, G. A.; Khanjin, N. A.; Menger, F. M. J. Chem. Soc., Chem. Commun. 1994, 2051. (c) Amato, M. E.; Lombardo, G. M.; Pappalardo, G. C.; Scarlata, G. J. Mol. Struct. 1995, 350, 71.
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144. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
145. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
146. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
147. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
148. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
149. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
150. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
151. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
152. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
153. The migratory aptitudes of guests moving through the annulus of several cyclodextrins have been computed; see: (a) Lü, T.-X.; Zhang, D.-B.; Dong, S.-J. J. Chem. Soc., Faraday Trans. 1989, 85, 1439. (b) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem. 1990, 55, 4772. (c) Ohashi, M.; Kasatani, K.; Shinohara, H.; Sato, H. J. Am. Chem. Soc. 1990, 112, 5824. (d) Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Mol. Struct. 1991, 248, 317. (e) Pang, L.; Whitehead, M. A. Supramol. Chem. 1992, 1, 81. (f) Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 55. (g) Fathallah, M.; Fotiadu, F.; Jaime, C. J. Org. Chem. 1994, 59, 1288. (h) Marconi, G.; Monti, S.; Mayer, B.; Köhler, G. J. Phys. Chem. 1995, 99, 3943. (i) Berg, U.; Gustavsson, M.; Åstrom, N. J. Am. Chem. Soc. 1995, 117, 2114. (j) See also refs 42h and 43a.
154. The first example of a self-included cyclodextrin CSP for gas chromatography has been reported; see: Bradshaw, J. S.; Chen, Z.; Yi, G.; et al. Anal. Chem. 1995, 67, 4437.
155. Preparation of thermally stable siloxane cyclodextrin rotaxanes for testing this hypothesis is in progress. V. Schurig, Tübingen, Germany, Personal communication. See also ref 7.
156. Lipkowitz, K. B. J. Chem. Educ. 1995, 72, 1070.
157. Dalgliesh, C. E. J. Chem. Soc. 1952, 137, 3940.