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Intermolecular hydrogen bonding in anilines and phenols can be subdivided into bonding involving solute molecules only, and into bonding involving both solute and solvent molecules. Interactions which do not involve hydrogen bonding are also possible between solute and solvent molecules. Spectral effects which may be associated with each of these interactions are described and discussed for anilines and phenols. By noting the effects of substituents on the various interactions, tentative conclusions can be deduced concerning the nature of these interactions.
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Dearden et al. (1960) studied this question.
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