INTRAMOLECULAR AND INTERMOLECULAR HYDROGEN BONDS IN AMINOPHENOLS

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 center dot center dot center dot O=S=O and N-H center dot center dot center dot 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 center dot center dot center dot 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.