Octakis[4-(2-phenylpropan-2-yl)phenylthio]naphthalene: A conformationally unique host allowing direct observation of a well-defined solid-state acetone conformation

Chemical Communications

Volumn , Issue 19, 1998, Pages 2085-2086

  Downing, Gary A ^a   Frampton, Christopher S ^b   MacNicol, David D ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3042770671     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805967e     Document Type: Article

References (15)

1. For a review see, D. D. MacNicol and G. A. Downing, in Comprehensive Supramolecular Chemistry, ed. D. D. MacNicol, F. Toda and R. Bishop, Pergamon, Oxford, 1996, vol. 6, ch. 14, pp. 431-444.
2. G. A. Downing, C. S. Frampton, J. H. Gall and D. D. MacNicol, Angew. Chem., Int. Ed. Engl., 1996, 35, 1547.
3. 2, 1,4-dioxane, and other solvents.
4. T. Iijima, Bull. Chem. Soc. Jpn., 1972, 45, 3526;
5. see also J. M. Vacherand, B. P. Van Eijck, J. Burie and J. Demaison, J. Mol. Spectosc., 1986, 118, 355.
6. Y. G. Smeyers, M. L. Senent, V. Botella and D. C. Moule, J. Chem. Phys., 1993, 98, 2754 and references cited therein.
7. With regard to the crystalline state, 1109 X-ray crystal structure analyses have been reported for systems in which acetone is present as a ligand component coordinated to a metal (e.g. R. Amstutz, J. D. Dunitz, T. Laube, W. B. Schweizer and D. Seebach, Chem. Ber., 1986, 119, 434;
8. M. Hoyer and H. Hartl, Z. Anorg. Allg. Chem., 1992, 612) or is 'anchored' in the lattice by one or more hydrogen bonds
9. (e.g. C. P. Brock and G. L. Morelan, J. Phys. Chem., 1986, 90, 5631). Both these situations tend to attenuate thermal motion, favouring direct observation of the acetone's hydrogen atoms, but represent relatively strong host-guest interactions. When such motion-reducing interactions are absent, the acetone molecule normally exhibits high thermal motion and/or disorder, however, see for example,
10. A. Dietrich, K. A. Fidelis, D. R. Powell, D. van der Helm and D. L. Eng-Wilmot, J. Chem. Soc., Dalton Trans., 1991, 231;
11. A. Avdeef and W. P. Scheafer, J. Am. Chem. Soc., 1976, 98, 5153. Interestingly, no X-ray results from the molecular crystal of acetone itself have yet appeared in the literature.
12. For a recent review of C-H⋯O interactions see, T. Steiner, Chem. Commun., 1997, 727.
13. J. Cosier and A. M. Glazer, J. Appl. Crystallogr., 1986, 19, 105.
14. G. M. Sheldrick, Acta Crystallogr., Sect. A., 1990, 46, 467.
15. G. M. Sheldrick, SHELXL-93, program for the refinement of crystal structures, University of Göttingen, Germany, 1993.