Issue 34, 2014

Folded alkyl chains in water-soluble capsules and cavitands

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

Supplementary files

Article information

Article type
Communication
Submitted
19 máj 2014
Accepted
10 júl 2014
First published
10 júl 2014

Org. Biomol. Chem., 2014,12, 6561-6563

Author version available

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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