Abstract
We have used IR Fourier spectroscopy to study intramolecular interactions in solutions of aminophenols in n-hexane. When the hydroxyl group in the molecule is ortho to the amino group, O-H⋯N and N-H⋯O intramolecular hydrogen bonds are formed in the aminophenols. Adding two tert-butyl groups to the benzene ring of ortho-aminophenols strengthens the O-H⋯N bond in the molecules, and prevents formation of an N-H⋯O bond. Additional acylation of the amino group in ortho-aminophenols leads to formation of an O-H⋯O=C intramolecular hydrogen bond. Formation of the above-indicated intramolecular hydrogen bonds in aminophenols affects the course of radiation-induced reactions occurring in n-hexane with participation of these compounds. The antioxidant properties of the aminophenols are enhanced when the hydroxyl groups in the molecules are found in the free state, and are diminished when strong O-H⋯N or O-H⋯O=C intramolecular hydrogen bonds are formed.
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References
E. T. Denisov and N. M. Emanuel’, Usp. Khim., 27, No. 4, 365–402 (1958).
V. A. Roginskii, Phenol Antioxidants. Reactivity and Efficacy [in Russian], Nauka, Moscow (1988).
N. Grassie and G. Scott, Polymer Degradation and Stabilisation [Russian translation], Nauka, Moscow (1988).
B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, 3rd Ed., Clarendon Press, Oxford (1999).
O. T. Andreeva, L. N. Dunets, P. T. Petrov, O. I. Shadyro, and V. M. Tsarenkov, “Antiviral drug for treatment of infections caused by the herpes simplex virus,” Belarus Patent No. 6503 (2004).
O. T. Andreeva, L. N. Dunets, P. T. Petrov, O. I. Shadyro, and V. M. Tsarenkov, “Anti-herpesvirus drug,” Belarus Patent No. 6594 (2004).
O. I. Shadyro, V. L. Sorokin, G. A. Ksendzova, G. I. Polozov, S. N. Nikolaeva, N. I. Pavlova, O. V. Savicheva, and E. I. Boreko, Khim.-Farmats. Zh., 37, No. 8, 5–7 (2003).
O. I. Shadyro, I. P. Edimecheva, G. K. Glushonok, N. I. Ostrovskaya, G. I. Polozov, H. Murase, and T. Kagiya, Free Radical Res., 37, No. 10, 1087–1097 (2003).
I. P. Edimecheva, N. I. Ostrovskaya, G. I. Polozov, and O. I. Shadyro, Zh. Obshch. Khim., 75, No. 4, 632–635 (2005).
G. A. Ksendzova, V. L. Sorokin, I. P. Edimicheva, and O. I. Shadyro, Khim. Vysok. Energ., 38, No. 6, 411–415 (2004).
G. A. Ksendzova, V. L. Sorokin, I. P. Edimecheva, and O. I. Shadyro, Free Radical Res., 38, No. 11, 1183–1190 (2004).
G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Collected Papers of the International Scientific Conference on Molecular, Membrane, and Cellular Basis for the Functioning of Biosystems, Seventh Meeting of the Belorussian Association of Photobiologists and Biophysicists, 21–23 June 2006 [in Russian], Pravo i Ekonomika IOOO, Minsk (2006), 1, pp. 93–95.
G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, O. I. Shadyro, and A. A. Yakunin, Opt. i Spektr., 102, No. 4, 602–607 (2007).
V. B. Vol’eva, T. N. Prokof’eva, A. I. Prokof’ev, I. S. Belostotskaya, N. A. Komisarova, and V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1789–1793 (1995).
O. I. Shadyro, V. L. Sorokin, G. A. Ksendzova, S. N. Nikolaeva, N. I. Pavlova, O. V. Savinova, and E. I. Boreko, Khim.-Farmats. Zh., 36, No. 8, 14–16 (2002).
F. Lober and K. Ley, “Method for preparation of o-aminophenols,” German Patent 1104522 (1959).
A. F. Hardman, “Process for preparing secondary amines,” US Patent 2238320 (1941).
A. G. Guimanini, G. Chiavari, M. M. Musiani, and P. Rossi, Synthesis, No. 9, 743–746 (1980).
T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York (1980).
P. A. Kollman and L. C. Allen, Chem. Rev., 72, No. 8, 283–303 (1972).
J. C. D. Brand and G. Eglinton, Applications of Spectroscopy to Organic Chemistry [Russian translation], Mir, Moscow (1967).
A. K. Pikaev, Modern Radiation Chemistry [in Russian], Nauka, Moscow (1986), Vol. 2.
V. V. Saraeva, Radiolysis of Hydrocarbons in the Liquid Phase [in Russian], Izdat. Mosk. Gos. Univ., Moscow (1986).
T. Gaumann and I. Hoigne, Aspects of Hydrocarbon Radiolysis, Academic Press, London (1968).
I. T. Kunjappu and K. N. Rao, Radiat. Phys. Chem., No. 13, 97–100 (1979).
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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 74, No. 5, pp. 577–582, September–October, 2007.
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Bel’kov, M.V., Ksendzova, G.A., Kuzovkov, P.V. et al. Intramolecular hydrogen bonds and antioxidant activity of aminophenols. J Appl Spectrosc 74, 635–641 (2007). https://doi.org/10.1007/s10812-007-0103-y
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DOI: https://doi.org/10.1007/s10812-007-0103-y