Alkyl Groups Fold to Fit within a Water-Soluble Cavitand

Am. Chem. Soc., 2014, 136(14), pp 5264–5266.

 

Kang-Da Zhang ‡, Dariush Ajami ‡, Jesse V. Gavette‡, and Julius Rebek , Jr.*†‡

 

 Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China and

 The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

 

Abstract

 

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 {Alpha},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.

Copyright © 2014 American Chemical Society.

 

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