Chelate effects in sulfate binding by amide/urea-based ligands

Org Biomol Chem. 2015 Jul 7;13(25):6953-7. doi: 10.1039/c5ob00618j. Epub 2015 May 13.

Abstract

The influence of chelate and mini-chelate effects on sulfate binding was explored for six amide-, amide/amine-, urea-, and urea/amine-based ligands. Two of the urea-based hosts were selective for SO4(2-) in water-mixed DMSO-d6 systems. Results indicated that the mini-chelate effect provided by a single urea group with two NH binding sites appears to provide enhanced binding over two amide groups. Furthermore, additional urea binding sites incorporated into the host framework appeared to overcome to some extent competing hydration effects with increasing water content.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemistry*
  • Binding Sites
  • Chelating Agents / chemistry*
  • Dimethyl Sulfoxide / chemistry
  • Ligands
  • Models, Molecular
  • Quaternary Ammonium Compounds / chemistry
  • Sulfates / chemistry*
  • Urea / analogs & derivatives*
  • Water / chemistry

Substances

  • Amides
  • Chelating Agents
  • Ligands
  • Quaternary Ammonium Compounds
  • Sulfates
  • Water
  • Urea
  • tetrabutylammonium
  • Dimethyl Sulfoxide