IR-Fourier spectroscopy methods are adopted to study intramolecular and intermolecular hydrogen bonds that form in CCl4 solutions of aminophenol derivatives and in a solid phase of these compounds pressed in KBr. If a hydroxyl group is present in the molecule in the ortho-position to an amino group, then intramolecular interactions between OH and NH groups will take place in aminophenol solutions. Intramolecular O–H⋅⋅⋅O=S=O and N–H⋅⋅⋅O=S=O hydrogen bonds are found in solutions of compounds containing a sulfonamide fragment. Additional acylation of the amino group causes an intramolecular O–H⋅⋅⋅O=C hydrogen bond to form in solutions. Functional groups OH, NH, SO2, and C=O interact with one another in various ways in the solid phase to form intermolecular hydrogen bonds in aminophenols.
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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 77, No. 4, pp. 535–541, July–August, 2010.
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Belkov, M.V., Ksendzov, G.A., Polozov, G.I. et al. Intramolecular and intermolecular hydrogen bonds in aminophenols. J Appl Spectrosc 77, 496–501 (2010). https://doi.org/10.1007/s10812-010-9359-8
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DOI: https://doi.org/10.1007/s10812-010-9359-8