Abstract
An infra-red investigation has been made of gas-phase hydrogen bonding between a range of amines and alcohols. Frequency displacements of the O—H stretching vibration have been obtained for some thirty gas-phase hydrogen bonded complexes. These displacements for a series of amines provide a measure of the relative electron donating abilities of the free amines: Et3N > Et2NH ≈ Me3N > Me2NH > EtNH2 > MeNH2 > NH3. Band contours for the O—H stretching mode of such gas-phase complexes are reported and discussed. These can be interpreted in terms of sum-and-difference bands of the O—H stretching vibration and the hydrogen bond stretching vibration. The interpretation can account for the qualitative changes in band contour that occur along a series of complexes. The systems considered include those formed by ammonia, methylamine, dimethylamine, trimethylamine, ethylamine and diethylamine with methanol, ethanol, isopropanol, t-butanol, and trifluoroethanol. Some complexes of triethylamine are also included.

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