Understanding the effects of preorganization, rigidity, and steric interactions in synthetic barbiturate receptors.

ABSTRACT: Synthetic barbiturate receptors have been utilized for many applications due to their high binding affinities for complementary guests. Although interest in this class of receptors spans from supramolecular to materials chemistry, the effects of receptor steric bulk and preorganization on guest binding affinity has not been studied systematically. To investigate the roles that steric bulk and preorganization play in guest binding, we prepared a series of 12 deconstructed Hamilton receptors with varying degrees of steric bulk and preorganization. Both diethylbarbital and 3-methyl-7-propylxanthine were investigated as guests for the synthetic receptors. The stoichiometry of guest binding was investigated using Job plots for each host-guest pair, and (1)H NMR titrations were performed to meas

SUBMITTER: McGrath JM 

PROVIDER: S-EPMC4002384 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature