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

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 [beta]-cyclodextrin ([beta]-CD) were studied using mass spectrometry, NMR spectrometry, isother...

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Published inSupramolecular chemistry Vol. 25; no. 6; p. 349
Main Authors Rouchal, Michal, Matelová, Alena, de Carvalho, Fabiana Pires, Bernat, Robert, Grbic, Dragan, Kuritka, Ivo, Babinský, Martin, Marek, Radek, Cmelík, Richard, Vícha, Robert
Format Journal Article
LanguageEnglish
Published Abingdon Taylor & Francis Ltd 01.06.2013
Subjects
Enzymes
Proteins
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Summary: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 [beta]-cyclodextrin ([beta]-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 102-103 M- 1. Stronger binding to the [beta]-CD cavity was observed for guests with a longer spacer between the adamantane and benzene moieties and/or a 1,4-disubstituted benzene ring. [PUBLICATION ABSTRACT]
ISSN:1061-0278
1029-0478
DOI:10.1080/10610278.2013.783916