Asymmetric binding of symmetric guests in a water-soluble cavitand. Issue 5 (3rd June 2018)

• Record Type: Journal Article
• Authors: Yu, Yang; Zhang, Kang-da; Petsalakis, Ioannis D.; Theodorakopoulos, Giannoula; Rebek, Julius
• Is Part Of: Supramolecular chemistry. Volume 30:Issue 5/6(2018)
• Page Start: 473
• Page End: 478
• Publication Date: 2018-06-03
• Subjects: Symmetric guest -- J-shaped conformation -- water-soluble cavitand; Macromolecules -- Periodicals; Supramolecular chemistry -- Periodicals; 547.005
• DOI: 10.1080/10610278.2017.1422868
• Languages: English
• ISSNs: 1061-0278

Abstract

Abstract: Binding of long aliphatic chains in water-soluble container compounds is driven by the hydrophobic effect: the CH2 groups of the guests are buried from water and solvate the inner aromatic surface of the host. The hydrophobic forces and the CH-π attractions are often sufficient to contort the guests into otherwise unfavorable shapes. Here we show that alkanes, α, ω-diols, α, ω-diacids and their methyl esters assume folded, J-shaped conformations in a water-soluble cavitand. The environment of the guest's ends interconvert rapidly on the NMR timescale through yo-yo like motions. The applications of water-soluble cavitands to reaction processes are discussed in the context of moving vs. fixed guest ends. Abstract :