Publication details
Adamantane-bearing benzylamines and benzylamides: novel building blocks for supramolecular systems with finely tuned binding properties towards beta-cyclodextrin
| Authors | |
|---|---|
| Year of publication | 2013 |
| Type | Article in Periodical |
| Magazine / Source | Supramolecular Chemistry |
| MU Faculty or unit | |
| Citation | |
| Web | DOI: 10.1080/10610278.2013.783916 |
| Doi | http://dx.doi.org/10.1080/10610278.2013.783916 |
| Field | Macromolecular chemistry |
| Keywords | adamantane; amines; cyclodextrins; binding properties; host–guest systems |
| Description | 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 b-cyclodextrin (b-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 M21. Stronger binding to the b-CD cavity was observed for guests with a longer spacer between the adamantane and benzene moieties and/or a 1,4-disubstituted benzene ring. |
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