A new dicarboxylic acid 4 was synthesized from 1,5-dichloroanthraquinone (1) and modified to ditopic receptors for binding of diammonium and dicarboxylate salts by multiple hydrogen bonds. The cis and trans isomers of 4 were assigned by the relative binding affinities of the bis(crown ether) derivatives, 5a and 5b to alkyl diammonium dipicrates. The association constants (K(a)) between p-substituted bis-phenylureas and adipate vary from 5 x 102 to 2 x 104 M-1 in DMSO-d6, depending on substituents in the phenyl ring.
Bibliographical noteFunding Information:
Acknowledgement This work was financially supported by the Basic Science Research Institute
Program, Ministry of Education (Project No. BSRI-94-3422).
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry