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

• Published in: Supramolecular chemistry Vol. 25; no. 6; pp. 349 - 361
• Main Authors: Rouchal, Michal, Matelová, Alena, de Carvalho, Fabiana Pires, Bernat, Robert, Grbić, Dragan, Kuřitka, Ivo, Babinský, Martin, Marek, Radek, Čmelík, Richard, Vícha, Robert
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01-06-2013
• Subjects: adamantane; amines; binding properties; cyclodextrins; host-guest systems
• ISSN: 1061-0278; 1029-0478
• DOI: 10.1080/10610278.2013.783916

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
-10
3
 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.