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Influence of the size of upper and lower rim substituents on the fluxional and complexation behaviour of calix[5]arenes

✍ Scribed by George Ferguson; Anna Notti; Sebastiano Pappalardo; Melchiorre F. Parisi; Anthony L. Spek

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
271 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A comparative study on a series of penta-O-alkylated p-H-calix[5]arenes lb-e and p-tertbutylcalix[5]arenes lg-m shows that the former are inherently mobile and adopt in solution non-cone conformations. The 1,2-alternate conformation for penta-O-benzyl ether lc was proven by single-crystal X-ray analysis. VT-NMR studies on lc-e have provided the first experimental evidence that conformational interconversion occurs via the p-phenyl-through-the-annulus mechanism with AG ~ in the range 17.9-18.8 kcal mol "1. Unlike the corresponding tert-butylated counterparts, p-H-calix[5]arenes ~e unable to form l: 1 endo-calix complexes with primary unbranched alkylammonium cations.

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