Self-recognition and hydrogen bonding by polycyclic bridgehead monoalcohols

Organic and Biomolecular Chemistry

Volumn 1, Issue 4, 2003, Pages 700-704

  Fraile, Amelia García ^a   Morris, David G ^b   Martínez, Antonio Garcia ^c   De La Moya Cerero, Santiago ^c   Muir, Kenneth W ^b   Ryder, Karl S ^d   Vilar, Enrique Teso ^a  

^a UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^d LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC PHYSICS; CRYSTAL STRUCTURE; CRYSTALLIZATION; CRYSTALLOGRAPHY; HYDROGEN BONDS; ISOMERS; MOLECULES; SOLIDS;

CRYSTALLOCHEMISTRY; ENANTIOMERS; POLYCYCLIC BRIDGEHEAD MONOALCOHOLS;

ALCOHOLS;

EID: 0038316302     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209427d     Document Type: Article

References (36)

1. (a) O. M. Yaghi, H.-L. Li, C. Davis, D. Richardson and T. L. Groy, Acc. Chem. Res., 1998, 31, 474-484
2. (b) O. M. Yaghi, H.-L. Li and T. L. Groy, J. Am. Chem. Soc., 1996, 118, 9096-9101
3. (c) L. Chen, M. Eddaoudi, S. T. Hyde, M. O'Keeffe and O. M. Yaghi, Science, 2001, 291, 1021-1023.
4. (a) S. S.-Y. Chui, S. M.-F. Lo, J. P. H. Charmant, A. G. Orpen and I. D. Williams, Science, 1999, 283, 1148-1150
5. (b) T. L. Henniga, D. C. MacQuarrie, P. Losier, R. D. Rogers and M. J. Zaworotko, Angew. Chem., Int. Ed., 1997, 36, 972-973
6. (c) K. Biradha, Y. H. Hongo and M. Fujita, Angew. Chem., Int. Ed., 2000, 39, 3843-3854.
7. (a) L. R. MacGillivray and J. L. Atwood, Nature, 1997, 389, 469-472
8. (b) V. A. Russell, C. C. Evans, W. Li and M. Ward, Science, 1997, 276, 575-579
9. (c) F. Garcia- Tellado, S. J. Geib, S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 1991, 113, 9265-9269.
10. D. G. Morris, K. S. Ryder, S. Walker, K. W. Muir, G. B. Hix and E. J. Maclean, Tetrahedron Lett., 2001, 42, 319-322.
11. J. P. Amoureux, M. Bee, C. Gore, V. Marin and P. Baert, Cryst. Struct. Commun., 1979, 8, 449-451.
12. J. A. Kanters, R. W. W. Hooft and A. J. M. Duisenberg, J. Crystallogr. Spectrosc. Res., 1990, 20, 123-131.
13. J. K. Harper, A. M. Arif and D. M. Grant, Acta Crystallogr. Sect. C: Cryst. Struct. Commun., 2000, 56, 451-452.
14. J. Bernstein, M. C. Etter and L. Leiserowitz, Structure Correlation, eds H.-B. Bürgie & J.D. Dunitz, vol. 2, pp. 432-507, VCH, Weinheim, Federal Republic of Germany, 1994.
15. (a) J. Bernstein, R. E. Davis, L. Shimoni and N. L. Chang, Angew. Chem., Int. Ed. Engl., 1995, 34, 1555-1573
16. (b) M. C. Etter, Acc. Chem. Res., 1990, 23, 120-126
17. (c) M. C. Etter, J. Phys. Chem., 1991, 95, 4601-4610
18. (d) M. C. Etter, J. C. MacDonald and J. Bernstein, Acta Crystallogr. Sect. B: Struct. Sci., 1990, 46, 256-262.
19. C. P. Brock and L. L. Duncan, Chem. Mater., 1994, 6, 1307-1312.
20. (a) F. H. Allen and O. Kennard, Chemical Design Automation News, 1993, 8(1), p.1 and pp. 31-37
21. (b) All structural searches were carried out locally using the QUEST and CONQUEST search programs with Version 5.22 of the Cambridge Structural Database (CSD), which was released in October 2001 with 245 392 entries. Statistics on the occurrence of crystal systems were obtained from the CSD mounted at the EPSRC Daresbury Laboratory, Daresbury, Warrington WA4 4AD, U.K. using CSSR software.
22. P. Murray-Rust and J. P. Glusker, J. Am. Chem. Soc., 1984, 106, 1018-1025.
23. A. Gavezotti, Structure Correlation, eds H.-B. Bürgi and J. D. Dunitz, vol. 2, page 521, VCH, Weinheim, Federal Republic of Germany, 1994.
24. T. C. W. Mak and G.-D. Zhou, Crystallography in Modern Chemistry, J. Wiley & Sons, New York, N.Y., USA, 1997, sections 216 and 3.1.
25. 1 axis in this classification.
26. (a) A. L. Spek, Acta Crystallogr. Sect. A: Found. Crystallogr., 1990, 46, C34
27. (b) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, A. L. Spek, 1998.
28. A. Nickon, T. Nishida, J. Franck and R. Munejuki, J. Org. Chem., 1971, 316, 1075-1078.
29. J. Libman, M. Sprecher and Y. Mazur, Tetrahedron, 1969, 25, 1679-1698.
30. (a) A. G. Martínez, E. T. Vilar, A. G. Fraile, C. R. Franco, J. S. Salvador, L. R. Subramanian and M. Hanack, Synthesis, 1987, 321-323
31. (b) B. L. Maroto, S. de la Moya Cerero, A. G. Martínez, A. G. Fraile and E. T. Vilar, Tetrahedron Lett., 2000, 41, 3059-3062
32. (c) A. G. Martínez, E. T. Vilar, A. G. Fraile, S. de la Moya Cerero and B. L. Maroto, Tetrahedron Lett., 2001, 42, 6539-6541.
33. P. Gosselin, M. Lelièvre and B. Poissonnier, Tetrahedron: Asymmetry, 2001, 12, 2091.
34. Programs used: SHELX97-Programs for Crystal Structure Analysis (Release 97-2). G. M. Sheldrick, Institut für Anorganische Chemie der Univesität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1998. WinGX - A Windows Program for Crystal Structure Analysis.
35. L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837.
36. DENZO-SCALEPACK Z. Otwinowski and W. Minor, Methods Enzymol., 1997, 276, 307-326.