Infrared Absorption Intensities of Out-of-plane CH Bending Vibrations of Substituted Benzenes. IV. Solvent Effect on the Intensities of the Bands of Aniline

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The infrared absorption intensities of out-of-plane CH bending and ring out-of-plane deformation vibrations of aniline have been measured in an acetone solvent mixed with various quantities of acetic acid. When such solvents are used, new peaks attributable to aniline interacting with the acid appear as shoulders of each of the original bands. A marked decrease in the sums of the intensities of the above two modes (Ao) has been observed for the bands of aniline interacting with the acid. It is demonstrated that the degree of such a decrease in intensity depends on the molar ratios of aniline and the acid. When there exists enough the acid in comparison with aniline, the values of Ao become minimum. On the other hand, when the numbers of the exsiting acetic acid molecules are much smaller than those of aniline, the values of Ao are considerably greater than those in the former case. In this case, a farily long time is needed until the interaction reaches an equilibrium state. Finally, when a very large amount of the acid is added, the bands attributable to aniline interacting with the acid are no longer observed. An attempt has been made to interpret these phenomena in terms of the state of the aggregation of aniline, acid and acetone molecules in the solutions.
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