Intramolecular hydrogen bonds in sulfur-containing aminophenols

• Published in: Journal of applied spectroscopy Vol. 77; no. 3; pp. 315 - 320
• Main Authors: Belkov, M. V., Harbachova, A. N., Ksendzova, G. A., Polozov, G. I., Skornyakov, I. V., Sorokin, V. L., Tolstorozhev, G. B., Shadyro, O. I.
• Format: Journal Article
• Language: English
• Published: Boston Springer US 01-07-2010; Springer
• Subjects: Analysis; Analytical Chemistry; Antiviral agents; Atomic/Molecular Structure and Spectra; Health aspects; Hydrogen; Hydrogen bonding; Infection; Physics; Physics and Astronomy; Sulfonamides; Telomerase; intramolecular interaction; virus inhibitor; IR spectrum; aminophenol; hydrogen bond
• ISSN: 0021-9037; 1573-8647
• DOI: 10.1007/s10812-010-9333-5

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.