Bis-amidocarbazolyl urea        receptor for short-chain dicarboxylate anions

M. Belén Jiménez; Victoria Alcázar; Rafael Peláez; Francisca Sanz; Ángel L. Fuentes de Arriba; M. Cruz Caballero

doi:10.1039/C1OB06540H

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Bis-amidocarbazolyl urea receptor for short-chain dicarboxylate anions†

M. Belén Jiménez,^a Victoria Alcázar,^b Rafael Peláez,^c Francisca Sanz,^d Ángel L. Fuentes de Arriba^a and M. Cruz Caballero*^a

Author affiliations

* Corresponding authors

^a Organic Chemistry Department, University of Salamanca, Plaza de los Caídos 1-5, Spain
E-mail: ccsa@usal.es
Fax: +34 9232 94574
Tel: +34 9232 94481

^b Industrial Chemistry and Environmental Engineering Department, Politechnique University of Madrid, José Gutiérrez Abascal 2, Spain

^c Pharmaceutical Chemistry Department, University of Salamanca, Campus Miguel de Unamuno, Spain

^d X-ray Diffraction Service, University of Salamanca, Plaza de los Caídos 1-5, Spain

Abstract

Urea receptor 1 based on two (1-amino-8-amido-3,6-dichloro)carbazole units shows a strong association with dicarboxylate anions such as oxalate, malonate and succinate guests through multiple hydrogen bonds from the carbazole, urea and amide NH groups. ¹H NMR complexation studies exhibit high values of association constants in DMSO-d₆. X-ray structures of the 1 : 1 complexes of 1 with oxalate and malonate as their ditetrabutylammonium salts were obtained. A modelling study of the complex of receptor 1 with succinate (as its diTBA salt) showed a more reduced geometric complementarity than its homologue malonate.

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Article information

DOI: https://doi.org/10.1039/C1OB06540H
Article type: Paper
Submitted: 06 Sep 2011
Accepted: 27 Oct 2011
First published: 27 Oct 2011

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Org. Biomol. Chem., 2012,10, 1181-1185

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Bis-amidocarbazolyl urea receptor for short-chain dicarboxylate anions

M. Belén Jiménez, V. Alcázar, R. Peláez, F. Sanz, Á. L. Fuentes de Arriba and M. C. Caballero, Org. Biomol. Chem., 2012, 10, 1181 DOI: 10.1039/C1OB06540H

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Organic & Biomolecular Chemistry