engleski

Adamantane Ammonium Salts as Guests for the Cyclodextrin Host: Something Old, Something New

Cyclodextrins (CDs) are important host macrocycles in supramolecular chemistry that possess deep, centrally positioned cavity, a structural feature essential for accommodation of hydrophobic guest molecules via their non-polar parts. Because of their properties and bioavailability, CDs have found application in pharmacology, biotechnology, catalysis, nanotechnology, etc.[1] Adamantane derivatives are known guest molecules that fit well into a CD cavity.[1] However, permethylated ammonium salts of adamantane have not been explored so far with this respect. Note that this class of compounds shows excellent binding abilities for cucurbituril hosts (CBs).[2] Inspired by these properties, we decided to broaden the scope of research regarding the binding between 1-substituited adamantane ammonium salts and CDs.[3] As a continuation of our study, herein we evaluated the binding capability of other regioisomers and the effect of other nitrogen-based functionalities on the complex stabilities. Various NMR spectroscopic techniques and ITC measurements were employed to determine the stability constants and explore host-guest interactions. Computational methods were used to gain more insight into structural features of formed complexes.

Cyclodextrins ; Adamantane Ammonium Salts ; Supramolecular Chemistry ; Host-guest complexes ; NMR titrations

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