N-Biphenyl thioureas as carboxylate receptors. Effect of the ligand substituents on the geometry of the complexes

Article abstract of DOI:10.1016/j.tet.2006.06.058

Six new biphenyl thiourea derivatives have been prepared to be used in carboxylate sensing. Experiments carried out with these ligands have demonstrated that the type of interaction with TBA carboxylates is strongly dependent on the substituents in the thiourea moiety. These interactions go from the formation of 1:1 hydrogen-bonded complexes to acid-base reactions. In addition, different geometries have been observed for the complexes being dependent on the conformations of the free ligands in solution.