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. 2008 Sep 4;10(17):3669-71.
doi: 10.1021/ol801228b. Epub 2008 Jul 26.

Recognition of guests by water-stabilized cavitand hosts

Agustí Lledó  1 , Richard J Hooley, Julius Rebek Jr
Affiliations

Recognition of guests by water-stabilized cavitand hosts

Agustí Lledó et al. Org Lett. .

Abstract

Water stabilized, deep cavitands with three walls and an open side are shown to be receptors for amines and ammonium cations bearing bulky aliphatic groups. The missing wall allows the binding of guests not accommodated by the four-walled counterparts.

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Figures

Figure 1
Figure 1
Synthesis of cavitands 3 and 4 and representation of 3 in the vase conformation.
Figure 2
Figure 2
1H NMR spectra (600 MHz) of (a) 3a in CDCl3/5% CD3OD, (b) 3a in CDCl3/D2O saturated, and (c) 3a + 6a in CDCl3/D2O saturated.
Figure 3
Figure 3
Structures of guests 6−13.
Figure 4
Figure 4
Upfield region in the 1H NMR spectra of 6a, 8, and 13 and their assignments.
Figure 5
Figure 5
Side views of a simplified model for the complex 3·2H2O and 6a (left) and 8 (right) showing different orientations of the adamantyl group.
None
See this image and copyright information in PMC

References

    1. Szumna A. Org. Biomol. Chem. 2007;5:1358–1368. - PubMed
    2. Hayashida O, Ito J, Matsumoto S, Hamachi I. Org. Biomol. Chem. 2005;3:654–660. - PubMed
    3. Saito S, Nuckolls C, Rebek J., Jr. J. Am. Chem. Soc. 2000;122:9628–9630.
    1. Lehn J-M, Meric R, Vingeron JP, Cesario M, Guilheim J, Pascard C, Asfari Z, Vicens J. Supramol. Chem. 1995;5:97.
    2. Atwood JL, Barbour LJ, Junk PC, Orr W. Supramol. Chem. 1995;5:105.
    3. Schneider H-J, Schneider U. J. Org. Chem. 1987;52:1613.
    4. Murayama K, Aoki K. Chem. Commun. 1997:119.
    1. Dalcanale E, Soncini P, Bacchilega G, Ugozzoli F. J. Chem. Soc., Chem. Commun. 1989:500–502.
    2. Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ. J. Org. Chem. 1989;54:1305–1312.
    3. Biros SM, Rebek J., Jr. Chem. Soc. Rev. 2007;36:93–104. - PubMed
    4. Rudkevich DM, Rebek J., Jr. Eur. J. Org. Chem. 1999;9:1991–2005.
    1. Soncini P, Bonsignore S, Dalcanale E, Ugozzoli F. J. Org. Chem. 1992;57:4608–4612.
    1. Ballester P, Sarmentero MA. Org. Lett. 2006;8:3477–3480. - PubMed
    2. Sarmentero MA, Ballester P. Org. Biomol. Chem. 2007;5:3046–3054. - PubMed

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