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Adamantane-retropeptides, new building blocks for molecular channels

Novel adamantane-oxalamide derivatives, N, N0-bis(1-adamantylglycine methyl ester)oxalamide (meso-1 and rac-1), N, N0-bis(3- aminoadamantane-1-carboxylic acid methyl ester)oxalamide (2) and N, N0-bis(3-aminoadamantane-1-carboxylic acid)oxalamide (3) were prepared and structurally characterized by spectroscopic methods and X-ray analysis. Crystal packing of the structures meso-1 and rac-1 is defined by one-dimensional a-networks of hydrogen-bonded chains. The crystal structures of 2 and 3 are characterized by two-dimensional b-networks of hydrogen bonds. The oxalamide 3 crystallizes as the solvates only. In the crystal structure of 3 the protic solvent participates in hydrogen bonding with the oxalamide moieties. However, in non-protic solvents 3 crystallizes as a solvate but the solvent does not participate in hydrogen bonding. The two-dimensional network of hydrogen bonds connecting molecules of 3 generates channels, which are filled by discrete solvent molecules.

adamantane-oxalamides; molecular channels; retropeptides; synthesis; X-ray structural analysis

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