𝔖 Bobbio Scriptorium
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A new slippage synthesis

✍ Scribed by Peter R. Ashton; Matthew C.T. Fyfe; Cesare Schiavo; J.Fraser Stoddart; Andrew J.P. White; David J. Williams

Book ID
104259552
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
294 KB
Volume
39
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

At elevated temperatures, the crown ether dibenzo [30]crown-10 (DB30C 10) slips over the (relatively) bulky 3,5-(t-Bu)2C6H3CH 2 termini of a bisammonium dication--bearing two secondary ammonium centers separated through a p-xylylene spacer--to form primarily a three-component rotaxane-like entity--stabilized by, inter alia, [N+-H...O] and [C-H...O] hydrogen bonds--that has been characterized by liquid secondary ion (LSI) mass spectrometry (in the "gas phase"), 1H NMR spectroscopy (in solution) and X-ray crystallography (in the solid state). However, this species equilibrates, in solution, with the free DB30C10 macrocycle and its two-component rotaxane-like congener, a result that demonstrates that the products obtained from the slippage synthesis are pseudorotaxanes.

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