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Exploring Structural and Thermodynamic Properties of Various Diamantane Amine–Cyclodextrin Complexes

Diamondoid ammonium salts are an intriguing class of compounds capable of forming ultra-stable complexes with cucurbituril (CB[n]) hosts in aqueous environment.[1] The host–guest chemistry of diamantane derivatives with different hydrophobic cavities, i.e., cyclodextrins (CDs), has not been explored as much.[2] We have therefore embarked on a study of inclusion complexes consisting of cage ammonium salts and CDs.[3] Herein we present the synthesis of a new series of diamantane amine derivatives and showcase the results of their binding with β- and γ-CDs. We used a diffusion NMR 1H-1H DOSY method to estimate the percentage of complexation based on the calculated diffusion coefficients. The binding strength of complexation was revealed by 1H NMR titrations, and the structural features of the complexes were assessed by the 1H-1H NOESY NMR experiments. Equilibrium constants and other thermodynamic parameters were additionally confirmed by ITC whereas computational studies revealed key interactions within the inclusion complexes.

Cyclodextrins ; Diamantane amine derivatives ; Supramolecular Chemistry ; Inclusion complex ; NMR spectroscopy ; Thermodynamics

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