The infrared spectra of the H2O, HDO, and D2O complexes with ethylene, propene, cis-2-butene, trans-2-butene, 2-methylpropene, 2-methyl-2-butene, 2,3-dimethyl-2-butene, 1,3-butadiene, benzene, and naphthalene have been recorded at temperatures from 11 to 20 K. Interaction energies have been estimated. HDO prefers to form a deuterium bond to the unsaturated molecule; however, small amounts of the hydrogen-bonded forms are present in thermal equilibrium with the deuterium-bonded forms. The energy difference between the hydrogen-bonded and deuterium-bonded forms has been estimated for most of the complexes.
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Engdahl et al. (1986) studied this question.