Intramolecular hydrogen bonds in sulfur-containing aminophenols

IR Fourier spectroscopy methods have been adopted to study intramolecular interactions that occur in CCl 4 solutions of antiviral derivatives of aminophenol. Analysis of the IR spectra showed that intramolecular bonds O–H···N, O–H···O=C, N–H···O=S=O, and O–H···O=S=O can occur in these compounds depending on the substituent on the amino group. Not only the presence of intramolecular O–H···N, O–H···O=S=O, and N– H···O=S=O hydrogen bonds in 2-amino-4,6-di-tert-butylphenol derivatives containing a sulfonamide fragment but also conformational equilibrium among these types of intramolecular interactions are essential for the manifestation of high efficiency in suppressing HIV-infection in cell culture.