Alkyl Groups Fold to Fit within a Water-Soluble Cavitand

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• 作者：Kang-Da Zhang ; Dariush Ajami ; Jesse V. Gavette ; Julius Rebek ; Jr.
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：April 9, 2014
• 年：2014
• 卷：136
• 期：14
• 页码：5264-5266
• 全文大小：262K
• 年卷期：v.136,no.14(April 9, 2014)
• ISSN：1520-5126

文摘

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 伪,蠅-diols are taken up in folded conformations. The guests鈥?termini are exposed to solvent while atoms near the alkane鈥檚 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.