Adamantane-bearing benzylamines and benzylamides: Novel building blocks for supramolecular systems with finely tuned binding properties towards β-cyclodextrin

Abstract

Novel building blocks for the synthesis of supramolecular components based on adamantane-bearing benzylamines were prepared. The binding properties of these amines and the corresponding acetamides towards β-cyclodextrin (β-CD) were studied using mass spectrometry, NMR spectrometry, isothermal titration calorimetry and semi-empirical calculations. It was found that all of the examined guests predominantly formed 1:1 inclusion complexes in an enthalpy-driven manner with association constants of the order of 10 2-103 M-1. Stronger binding to the β-CD cavity was observed for guests with a longer spacer between the adamantane and benzene moieties and/or a 1,4-disubstituted benzene ring. © 2013 Taylor & Francis Group, LLC.