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Threading of Conformationally Stable Calix[6]arene Wheels Substituted at the Methylene Bridges (CROSBI ID 268371)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Tranfic Bakic, Marina ; Iuliano, Veronica ; Talotta, Carmen ; Geremia, Silvano ; Hickey, Neal ; Spinella, Aldo ; De Rosa, Margherita ; Soriente, Annunziata ; Gaeta, Carmine ; Neri, Placido Threading of Conformationally Stable Calix[6]arene Wheels Substituted at the Methylene Bridges // Journal of organic chemistry, 84 (2019), 18; 11922-11927. doi: 10.1021/acs.joc.9b01779

Podaci o odgovornosti

Tranfic Bakic, Marina ; Iuliano, Veronica ; Talotta, Carmen ; Geremia, Silvano ; Hickey, Neal ; Spinella, Aldo ; De Rosa, Margherita ; Soriente, Annunziata ; Gaeta, Carmine ; Neri, Placido

engleski

Threading of Conformationally Stable Calix[6]arene Wheels Substituted at the Methylene Bridges

Calix[6]arenes disubstituted at the methylene bridges, which are stable in the cone or 1, 2, 3- alternate conformation, form pseudorotaxanes with dialkylammonium axles. The cone-wheel based pseudorotaxanes are 10-100 times more stable than those obtained with the native conformationally- mobile calix[6]arene wheel, as a consequence of their higher degree of preorganization. The threading of conformationally stable 1, 2, 3- alternate-calix[6]arenes is unprecedented in the literature. Therefore, very peculiar NMR features are here evidenced for this threading process involving the less symmetrical 1, 2, 3-alternate calix[6]arene conformation, which implies a peculiar rototranslation motion of the axle.

calix[6]arene ; threading ; pseudorotaxane

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Podaci o izdanju

84 (18)

2019.

11922-11927

objavljeno

0022-3263

1520-6904

10.1021/acs.joc.9b01779

Povezanost rada

Kemija

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