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- W2315161928 abstract "A complete study of the through-the-annulus threading of the larger calix[8]arene macrocycle with di-n-alkylammonium cations has been performed in the presence of the “superweak” TFPB counterion. Thus, it was found that such threading occurs only upon partial preorganization of the calix[8]arene macroring by intramolecular bridging. In particular, 1,5-bridged calix[8]arenes with a meta- or para-xylylene bridge (2 and 3) gave pseudo[2]rotaxanes in which one dialkylammonium axle (4a–4e+) was threaded into one of the two subcavities of the calix[8]-wheel. Conformational studies by using chemical shift surface maps and DFT calculations evidenced a 3/4-cone geometry for these subcavities. Higher pseudorotaxane Kass values were obtained for calix[8]-wheels 2 and 3, with respect to calix[6]-host 1a, due to the cooperative effect of their two subcavities. Dynamic NMR studies on calix[8]-pseudorotaxanes evidenced a direct correlation between Kass (and ΔGass) values and energy barriers for calix inversion due to the effectiveness of thread templation. In accordance with DFT calculations, an endo-alkyl preference, over the endo-benzyl one, was observed by threading calix[8]-wheel 3 with the directional n-butylbenzylammonium axle 4d+." @default.
- W2315161928 created "2016-06-24" @default.
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- W2315161928 creator A5064668573 @default.
- W2315161928 creator A5086129882 @default.
- W2315161928 date "2013-07-23" @default.
- W2315161928 modified "2023-10-07" @default.
- W2315161928 title "Through-the-Annulus Threading of the Larger Calix[8]arene Macrocycle" @default.
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- W2315161928 doi "https://doi.org/10.1021/jo401206j" @default.
- W2315161928 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23834296" @default.
- W2315161928 hasPublicationYear "2013" @default.
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