The effect of intramolecular hydrogen bonding on the thermodynamics of partitioning of an isomer of the histamine H2-receptor antagonist metiamide

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Abstract
The thermodynamics of transfer from water to 1−octanol of the 4 and 5 substituted N-methylimidazole isomers of the H2-receptor antagonist metiamide have been determined. The isomers have similar free energies of transfer but the enthalpy and entropy of transfer of the 4−isomer are substantially greater than those of the 5−isomer. This indicates that the 4−isomer forms an intramolecular hydrogen bond in the polar octanol phase.