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Issue 34, 2014
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Folded alkyl chains in water-soluble capsules and cavitands

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Abstract

A deep cavitand with ionic “feet” dimerizes around hydrophobic compounds in D2O. Longer n-alkane guests, C14–C18, are encapsulated in contorted conformations and NMR is used to deduce their shapes. Competition experiments establish the driving forces involved and how they compensate for the steric clashes in the folded structures of the encapsulated alkanes. Bolaamphiphiles instead prefer to bind in the monomeric cavitand with conformations that bury the methylenes but expose the polar head groups to solvent.

Graphical abstract: Folded alkyl chains in water-soluble capsules and cavitands

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Publication details

The article was received on 19 May 2014, accepted on 10 Jul 2014 and first published on 10 Jul 2014


Article type: Communication
DOI: 10.1039/C4OB01032A
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Citation: Org. Biomol. Chem., 2014,12, 6561-6563
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    Folded alkyl chains in water-soluble capsules and cavitands

    J. V. Gavette, K. Zhang, D. Ajami and J. Rebek, Org. Biomol. Chem., 2014, 12, 6561
    DOI: 10.1039/C4OB01032A

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