Alkyl groups fold to fit within a water-soluble cavitand

We report here a widened, deep cavitand host that binds hydrophobic and amphiphilic guests in D2O. Small alkanes (C6 to C11) are bound in compressed conformations and tumble rapidly within the space. Longer n-alkanes (C13 to C14), n-alcohols, and α,ω-diols are taken up in folded conformations. The g...

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Bibliographic Details
Published in:Journal of the American Chemical Society, Vol. 136, No. 14 (2014), p. 5264-6
Main Author: Zhang, Kang-Da
Other Involved Persons: Ajami, Dariush ; Gavette, Jesse V ; Rebek, Julius Jr
Format: electronic Article
Language:English
ISSN:1520-5126
Item Description:Date Completed 20.04.2015
Date Revised 09.04.2014
published: Print-Electronic
Citation Status MEDLINE
Copyright: From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Physical Description:Online-Ressource
DOI:10.1021/ja501685z
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  • We report here a widened, deep cavitand host that binds hydrophobic and amphiphilic guests in D2O. Small alkanes (C6 to C11) are bound in compressed conformations and tumble rapidly within the space. Longer n-alkanes (C13 to C14), n-alcohols, and α,ω-diols are taken up in folded conformations. The guests' termini are exposed to solvent while atoms near the alkane's center are buried and protected. The cavitand acts as a concave template that pushes terminal atoms of the guest closer together. The unexpected binding modes are interpreted in terms of the size and shape of the space accessible in the new cavitand