engleski

Synthesis, NMR and single crystal X-ray crystallographic characterization of novel 2, 6-diaminoadamantane salts

The synthesis of amines and their derivatives has been of interest for quite some time because of their use as therapeutics. There has also been considerable attention paid to adamantane amines due to their possible biological activity, in particular as potential antiviral agents.[1] Until now a large number of adamantane amines have been synthesized but, to the best of our knowledge, no adamantyldiamino-derivatives substituted at positions 2 and 6 were synthesized or studied. Adamantane-2, 6-diammonium salts 2-4 were prepared from adamantane-2, 6-dione [2] by reduction of the corresponding dioxime 1 [3] to the diamine dihydrochloride 2a which was the starting material for the synthesis of all the other salts that were investigated. An extensive repertoire of 1D/2D NMR experiments enabled complete 1H and 13C assignments in the spectra of salts 2-4 that was consistent with their C2-symmetry axial-chirality geometries. Salt 3 crystallized as a 2.5 hydrate with inversion pseudosymmetry between two molecules of opposite handedness in the asymmetric unit of a P-1 racemic compound crystal. A high fidelity for the crystallographic inversion pseudosymmetry measure rmS(i) [4] was found for the approximate inversion relationship between the two almost enantiomeric molecules in the asymmetric unit.

Adamantane-2; 6-diammonium salts; adamantane-2; 6-dione; X-ray

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