engleski

Crystal structures of two 3-cyclohexanemethyl hydantoin derivatives

Hydantoins have been used as anticonvulsive drugs and herbicides, as well as useful intermediates in the synthesis of polymer-drug conjugates. In the present study we report crystal and molecular structures of two hydantoin derivatives: 3-cyclohexanemethyl-5- isopropyl hydantoin (1) and 3- cyclohexanemethyl-5-isobutyl hydantoin (2). These two structures differ only in the side chain attached to the hydantoin ring (isopropyl in 1, isobutyl in 2), and they are conformationaly very similar. The molecules are joined by the same hydrogen-bonding motifs, involving the same donor and acceptor atoms. Thus, the intermolecular N-H• • • O hydrogen bond in 1 and 2 generates an infinite C(5) chains, and C-H• • • O intermolecular hydrogen bond forms infinite C(7) chains. These hydrogen bonds are reinforced by that of a C-H• • • O hydrogen bond in 1 and three C-H• • • O hydrogen bonds in 2, so producing two- dimensional networks. The networks are separated by hydrophobic channels in both crystal structures, but in 2, the hydrogen- bonded molecules are assembled in such manner that they form cavities along a axis.

hydantoin derivatives ; X-ray crystal structure ; hydrogen-bonding

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