We have used Fourier transform IR (FTIR) spectroscopy to study intramolecular interactions in solutions of 4,6-di-tert-butyl-2-aminophenol in n-hexane. When the hydroxyl group in the molecule is ortho to the amino group, an O―H⋅⋅⋅N intramolecular hydrogen bond is formed in the 4-6-di-tert-butyl-2-aminophenol derivatives, where the strength of the hydrogen bond depends on the type of substituent at the para position of the phenyl ring. If there are electron-donor groups on the phenyl ring, then a stronger O―H⋅⋅⋅N bond is formed in the 4,6-di-tert-butyl-2-aminophenol derivatives than in molecules containing electron-acceptor Cl and Br atoms. Formation of the above-indicated intramolecular hydrogen bond affects the course of radiation-induced reactions occurring in n-hexane with participation of these compounds and also affects their antiviral activity.
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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 76, No. 3, pp. 434–439, May–June, 2009.
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Belkov, M.V., Ksendzova, G.A., Polozov, G.I. et al. Intramolecular interactions in antiviral derivatives of 4,6-di-tert-butyl-2-aminophenol. J Appl Spectrosc 76, 408–413 (2009). https://doi.org/10.1007/s10812-009-9194-y
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DOI: https://doi.org/10.1007/s10812-009-9194-y