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

Gruber, Tobias and Gruner, Margit and Fischer, Conrad and Seichter, Wilhelm and Bombicz, Petra and Weber, Edwin (2010) Conformational behaviour and first crystal structures of a calix[4]arene featuring a laterally positioned carboxylic acid function in unsolvated and solvent-complexed forms. New Journal of Chemistry, 34 (2). p. 250. ISSN 1144-0546

Full content URL: http://dx.doi.org/10.1039/B904489B

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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

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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.

Keywords:calixarene, cyclophane, Organic synthesis, X-ray diffraction, Molecular Conformation, Chirality
Subjects:F Physical Sciences > F131 Crystallography
F Physical Sciences > F200 Materials Science
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F130 Structural Chemistry
Divisions:College of Science > School of Pharmacy
ID Code:20031
Deposited On:15 Jan 2016 11:41

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