Abstract
THE encapsulation of molecules within larger molecular or supramolecular cages (see ref. 1 for examples) brings about many interesting phenomena, among them the stabilization of reactive intermediates2, new forms of stereoisomerism3, and templating of the cage itself4,5. Here we describe a self-assembling hydrogen-bonded molecular capsule that encapsulates guest molecules in a reversible, apparently entropy-driven process, giving rise to unusual temperature dependence of the formation process. The positive entropy of formation—at first sight unexpected—seems to be the result of the fact that more than one solvent molecule is included in the 'bare' cage, making their replacement by a single large molecule (here adamantane or ferrocene) entropically favourable.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Cram, D. J. Nature 356, 29–36 (1992).
Cram, D. J. & Tanner, M. E. Angew. Chem. (int. edn Engl.) 30, 1024–1027 (1991).
Timmerman, P. et al. Angew. Chem. (int. edn Engl.) 33, 2345–2348 (1994).
Chapman, R. G. & Sherman, J. C. J. Am. chem. Soc. 117, 9081–9082 (1995).
Chapman, R. G., Chopra, N., Cochien, E. D. & Sherman, J. C. J. Am. chem. Soc. 116, 369–370 (1994).
Meissner, R. S., Rebek, J. Jr & Mendoza, J. D. Science 270, 1485–1488 (1995).
Lindsey, J. S. New J. Chem. 15, 153–180 (1991).
Dunitz, J. D. Chem. Biol. 2, 709–712 (1995).
Peterson, B. R., Wallimann, P., Carcanague, D. R. & Diederich, F. Tetrahedron 51, 401–421 (1995).
Searle, M. S., Westwell, M. S. & Williams, D. H. J. chem. Soc. Perkin Trans. 2, 141–151 (1995).
Canceill, J. et al. Angew. Chem. (int. edn Engl.) 28, 1246–1248 (1989).
Cram, D. J., Choi, H.-J., Bryant, J. A. & Knobler, C. B. J. Am. chem. Soc. 114, 7748–7765 (1992).
Cram, D. J., Blanda, M. T., Paek, K. & Knobler, C. B. J. Am. chem. Soc. 114, 7765–7773 (1992).
Shimizu, K. D. & Rebek, J. Jr Proc. natn. Acad. Sci. U.S.A. 92, 12403–12407 (1995).
Mock, W. L., Irra, T. A., Wepsiec, J. P. & Adhya, M. J. org. Chem. 54, 5302–5308 (1989).
Walter, C. J., Anderson, H. L. & Sanders, J. K. M. J. chem. Soc. chem. Commun. 458–460 (1993).
Mohamadi, F. et al. J. Comput. Chem. 11, 440–467 (1990).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kang, J., Rebek, J. Entropically driven binding in a self-assembling molecular capsule. Nature 382, 239–241 (1996). https://doi.org/10.1038/382239a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/382239a0
This article is cited by
-
Modifying electron injection kinetics for selective photoreduction of nitroarenes into cyclic and asymmetric azo compounds
Nature Communications (2022)
-
Solvent effects on host-guest residence time and kinetics: further insights from metadynamics simulation of Toussaintine-A unbiding from chitosan nanoparticle
Journal of Molecular Modeling (2021)
-
Strategies for binding multiple guests in metal–organic cages
Nature Reviews Chemistry (2019)
-
Controlled release from cucurbituril
Journal of Inclusion Phenomena and Macrocyclic Chemistry (2017)
-
Taking on the turnover challenge
Nature Chemistry (2016)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
