Issue 2, 2010
From the journal:

New Journal of Chemistry

Conformational behaviour and first crystal structures of a calix[4]arene featuring a laterally positioned carboxylic acid function in unsolvated and solvent-complexed forms†

Tobias Gruber,‡a   Margit Gruner,b   Conrad Fischer,a   Wilhelm Seichter,a   Petra Bombiczc  and  Edwin Weber*a  

* Corresponding authors

a Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Str. 29, D-09596 Freiberg/Sachs., Germany
E-mail: edwin.weber@chemie.tu-freiberg.de
Fax: +49-3731-39 31 70

b Institut für Organische Chemie, Technische Universität Dresden, Mommsenstr. 13, D-01062 Dresden, Germany

c Institute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, P. O. Box 17, H-1525 Budapest, Hungary

Abstract

A detailed conformational analysis of a rarely investigated type of compound, a laterally monosubstituted calix[4]arene (1, which has a carboxylic acid function in the lateral position), is reported. 2D solution NMR techniques at various temperatures and in different solvents have been used, showing interesting aggregation behaviour for the different conformers. The first illustrations of crystal structures of this compound type are given, including the unsolvated carboxylic calix[4]arene and two mixed solvent complexes containing EtOH–H2O and EtOH–THF, respectively. Isostructurality calculations have been carried out, allowing detailed comparison of the investigated structures, and an unusual conformational chirality isomerism of the calixarene molecule is demonstrated.

Graphical abstract: Conformational behaviour and first crystal structures of a calix[4]arene featuring a laterally positioned carboxylic acid function in unsolvated and solvent-complexed forms

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Article information

DOI
https://doi.org/10.1039/B904489B
Article type
Paper
Submitted
04 Mar 2009
Accepted
04 Nov 2009
First published
05 Jan 2010

New J. Chem., 2010,34, 250-259

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Conformational behaviour and first crystal structures of a calix[4]arene featuring a laterally positioned carboxylic acid function in unsolvated and solvent-complexed forms

T. Gruber, M. Gruner, C. Fischer, W. Seichter, P. Bombicz and E. Weber, New J. Chem., 2010, 34, 250 DOI: 10.1039/B904489B

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