Pyrrole-pyridine and pyrrole-naphthyridine hosts for anion recognition

Molecules. 2015 May 27;20(6):9862-78. doi: 10.3390/molecules20069862.

Abstract

The association constants of the complexes formed by two hosts containing pyrrole, amide and azine (pyridine and 1,8-naphthyridine) groups and six guests, all monoanions (Cl-, CH3CO2-, NO3-, H2PO4-, BF4-, PF6-), have been determined using NMR titrations. The X-ray crystal structure of the host N2,N5-bis(6-methylpyridin-2-yl)-3,4-diphenyl-1H-pyrrole- 2,5-dicarboxamide (1) has been solved (P21/c monoclinic space group). B3LYP/6-31G(d,p) and calculations were carried out in an attempt to rationalize the trends observed in the experimental association constants.

Keywords: B3LYP/6-31G(d,p) calculations; NMR titrations; X-ray structures; anion binding; association constants.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Anions / analysis*
  • Crystallography, X-Ray
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Naphthyridines / chemical synthesis
  • Naphthyridines / chemistry*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Quantum Theory
  • Thermodynamics

Substances

  • Amides
  • Anions
  • Naphthyridines
  • Pyridines
  • Pyrroles