A1 Journal article (refereed)
Structural Studies of Self-Folding Cavitands (2000)


Shivanyuk, A., Rissanen, K., Körner, S., Rebek, J., & Rudkevich, D. (2000). Structural Studies of Self-Folding Cavitands. Helvetica Chimica Acta, 83(8), 1778-1790. https://doi.org/10.1002/1522-2675(20000809)83:8%3C1778::AID-HLCA1778%3E3.0.CO;2-J


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Publication details

All authors or editors: Shivanyuk, Alexander; Rissanen, Kari; Körner, Steffi; Rebek, Julius; Rudkevich, Dmitry

Journal or series: Helvetica Chimica Acta

Publication year: 2000

Volume: 83

Issue number: 8

Pages range: 1778-1790

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.1002/1522-2675(20000809)83:8%3C1778::AID-HLCA1778%3E3.0.CO;2-J

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Abstract

Resorcinarene-based cavitands 1a – c fold into a deep open-ended cavity by means of intramolecular hydrogen bonds in both apolar solutions and the solid state. The X-ray crystal-structure analysis of cavitand 1a features a seam of secondary amide C=O⋅⋅⋅H−N interactions that bridge adjacent rings and are held in place by intra-annular hydrogen bonds. This results in a cavity of 9.2×7.0 Å dimensions. The arrangement of the amides in 1a – 1c is cycloenantiomeric, with clock- and counterclockwise orientation of the head-to-tail amide sequence. Interconversion rates of the two enantiomers are controlled by solvent polarity: the rate is slow on the NMR time-scale in aromatic solvents and CDCl3, but fast in (D6)acetone. The 1H- and 13C-NMR-spectral analysis is in agreement with the crystallographic data. Chiral cavitand 1b with eight HN−C(O)−C*HMeEt ((+)-(S)) groups on its upper rim exists as two cyclodiastereoisomers (in a ca. 3 : 1 ratio) in apolar solution. A `library' of 512 diastereoisomeric cavitands 1c is obtained as a mixture by using the corresponding racemic acid chloride.


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