A series of synthetic receptors with strong selectivity for the barbiturate family of drugs has been prepared. The receptor design is based on two 2,6-diaminopyridine groups linked through an isophthalic acid spacer. X-ray crystallographic, 1H NMR spectroscopic, and substrate binding studies confirm that six hydrogen bonds are formed between the receptor and its substrate. The strongest binding (Ka≈ 105 M−1) is seen to those substrates containing the complementary barbituric acid core. Systematic deletion of hydrogen-bonding sites from the receptor and substrate allows an assessment of the contribution of individual binding sites to complexation.
ASJC Scopus subject areas
- Colloid and Surface Chemistry