Hydrogen-bonded chains of α,ω-diaminoalkane and α,ω-dihydroxyalkane guest molecules lead to disrupted tunnel structures in urea inclusion compounds

New Journal of Chemistry

Volumn 29, Issue 10, 2005, Pages 1266-1271

  Lee, Sang Ok ^a   Kariuki, Benson M ^a   Harris, Kenneth D M ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; UREA DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; GEOMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 27344442153     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b502004m     Document Type: Article

References (31)

1. A. E. Smith, Acta Crystallogr., 1952, 5, 224.
2. R. W. Schiessler and D. Flitter, J. Am. Chem. Soc., 1950, 74, 1720.
3. L. C. Fetterly, in Non-stoichiometric Compounds, ed. L. Mandelcorn, Academic Press, New York, 1964, pp. 491.
4. M. D. Hollingsworth and K. D. M. Harris, in Comprehensive Supramolecular Chemistry, ed. D. D. MacNicol, F. Toda and R. Bishop, Pergamon Press, Oxford, 1996, vol. 6, pp. 177.
5. K. D. M. Harris, Chem. Soc. Rev., 1997, 26, 279.
6. F. Guillaume, J. Chim. Phys. Phys.-Chim. Biol., 1999, 96, 1295.
7. K. D. M. Harris, in Encyclopaedia of Supramolecular Chemistry, ed. J. L. Atwood and J. W. Steed, Marcel Dekker, New York, 2004, vol. 2, pp. 1538-1549.
8. K. D. M. Harris and J. M. Thomas, J. Chem. Soc., Faraday Trans., 1990, 86, 2985.
9. h is not equal to a rational number with sufficiently small denominator. General aspects concerning the nature of incommensurate vs. commensurate behaviour in tunnel inclusion compounds (ref. 10) and specific issues relating to urea inclusion compounds (ref. 8, 11-14) are discussed in the references cited.
10. A. J. O. Rennie and K. D. M. Harris, Proc. R. Soc., Ser. A, 1990, 430, 615.
11. K. D. M. Harris and M. D. Hollingsworth, Proc. R. Soc., Ser. A, 1990, 431, 245.
12. S. van Smaalen and K. D. M. Harris, Proc. R. Soc., Ser. A, 1996, 452, 677.
13. R. Lefort, J. Etrillard, B. Toudic, F. Guillaume, T. Breczewski and P. Bourges, Phys. Rev. Lett., 1996, 77, 4027.
14. T. Weber, H. Boysen, F. Frey and R. B. Neder, Acta Crystallogr., Sect. B: Struct. Sci., 1997, 53, 544.
15. S. P. Smart, PhD Thesis, University of St. Andrews, 1993.
16. M. D. Hollingsworth, B. D. Santarsiero and K. D. M. Harris, Angew. Chem., Int. Ed. Engl., 1994, 33, 649.
17. M. E. Brown, J. D. Chaney, B. D. Santarsiero and M. D. Hollingsworth, Chem. Mater., 1996, 8, 1588.
18. M. D. Hollingsworth, M. E. Brown, A. C. Hillier, B. D. Santarsiero and J. D. Chaney, Science, 1996, 273, 1355.
19. M. D. Hollingsworth, U. Werner-Zwanziger, M. E. Brown, J. D. Chaney, J. C. Huffman, K. D. M. Harris and S. P. Smart, J. Am. Chem. Soc., 1999, 121, 9732.
20. K. Suchiro, A. Urabe, Y. Yoshitake and Y. Nagano, Makromol. Chem., 1984, 185, 2467.
21. A. Chenite and F. Brisse, Macromolecules, 1991, 24, 2221.
22. A. Chenite and F. Brisse, Macromolecules, 1992, 25, 776.
23. P. Eaton, N. Vasanthan, I. D. Shin and A. E. Tonelli, Macromolecules, 1996, 29, 2531.
24. S.-O. Lee, B. M. Kariuki, A. L. Richardson and K. D. M. Harris, J. Am. Chem. Soc., 2001, 123, 12684.
25. S.-O. Lee, B. M. Kariuki and K. D. M. Harris, manuscript in preparation.
26. S.-O. Lee, B. M. Kariuki and K. D. M. Harris, Angew. Chem., Int. Ed., 2002, 41, 2181.
27. SHELX-97, G. M. Sheldrick, Programs for Crystal Structure Analysis (Release97-2), University of Göttingen, Germany, 1997.
28. 2 groups are such that they lie above and below the plane of the circle that would be circumscribed by rotating the H atom of the OH group about the C-O bond. Therefore, no significant improvements to the O-H⋯N hydrogen bond geometries for the two disorder components would be achieved by allowing there to be two H atom positions (corresponding to rotation about the C-O bond) with fractional occupancies in the refinement calculations.
29. M. C. Etter, Acc. Chem. Res., 1990, 23, 120.
30. M. C. Etter, J. C. MacDonald and J. Bernstein, Acta Crystallogr., Sect. B: Struct. Sci., 1990, 46, 256.
31. J. Bernstein, R. E. Davis, L. Shimoni and N. L. Chang, Angew. Chem., Int. Ed. Engl., 1995, 34, 1555.