Molecular recognition of alkylammonium contact ion-pairs using a ditopic receptor.
A ditopic, macrobicyclic receptor with adjacent anion and cation binding sites is able to distinguish between various monoalkylammonium salts by binding them as contact ion-pairs. The affinity for linear n-propylammonium chloride is at least 2 orders of magnitude greater than that for n-propylammonium acetate, n-propylammonium p-toluenesulfonate, and branched isopropylammonium chloride. An X-ray structure of the receptor complexed with methylammonium chloride illuminates the basis of the molecular recognition.
Mahoney
Joseph M
JM
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA. smith.115@nd.edu
Davis
John P
JP
Beatty
Alicia M
AM
Smith
Bradley D
BD