Conformational properties of methylene bridged resorcarenes

Conformations and conformational interconversions of resorcarene 1c have been studied by molecular mechanics calculations. As with calix[4]arenes the general stability of the four basic conformations is cone > partial cone > 1,2-alternate > 1,3-alternate. The lowest energy is calculated for...

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Bibliographic Details
Published in:Tetrahedron 1998-10, Vol.54 (42), p.12823-12828
Main Authors: Thondorf, Iris, Brenn, Jörg, Böhmer, Volker
Format: Article
Language:English
Subjects:
Calixarenes
Conformation
Molecular mechanics
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Summary:Conformations and conformational interconversions of resorcarene 1c have been studied by molecular mechanics calculations. As with calix[4]arenes the general stability of the four basic conformations is cone > partial cone > 1,2-alternate > 1,3-alternate. The lowest energy is calculated for a pinched cone conformer with C 2v symmetry stabilised by intramolecular hydrogen bonds of the two “parallel” resorcinol units as donors. The topomerisation of the cone conformation proceeds via the partial cone and 1,2-alternate intermediates with a calculated barrier of 9.9 kcal mol −1 which is in excellent agreement with the experimental value. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00771-6