Bis-amidocarbazolyl urea receptor for short-chain dicarboxylate anions

Org Biomol Chem. 2012 Feb 14;10(6):1181-5. doi: 10.1039/c1ob06540h. Epub 2011 Dec 19.

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. (1)H NMR complexation studies exhibit high values of association constants in DMSO-d(6). 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Carbazoles / chemistry*
  • Crystallography, X-Ray
  • Dicarboxylic Acids / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Urea / analogs & derivatives
  • Urea / chemical synthesis
  • Urea / chemistry*

Substances

  • (1-amino-8-amido-3,6-dichloro)carbazole
  • Anions
  • Carbazoles
  • Dicarboxylic Acids
  • Urea