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 May 2014
Accepted
10 Tem 2014
First published
10 Tem 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements