Abstract
From an examination of the frequencies, integral intensities, and half-widths of the absorption bands of the stretching vibrations of the hydroxyl groups in the IR spectra, it was concluded that 3-hydroxyquinoline, 4-hydroxyisoquinoline, and their derivatives exist in the phenol form in dilute CCl4 solutions. Strong intermolecular hydrogen bonds, which are destroyed on dilution, exist in 3-hydroxyquinoline, 4-methyl-3-hydroxyquinoline, 4-hydroxyisoquinoline, and 1-chloro-3-methyl-4-hydroxyquinoline at concentrations above 102 M in CCl4. From an examination of the values of halo derivatives of 3-hydroxyquinoline and 4-hydroxyisoquinoline, it was concluded that an intramolecular hydrogen bond of the OH...Hal type is present in these compounds. The shift in the OH band increases in the order Cl< Br< I. Weak bands of a free OH group that pertain to the s-trans form are observed in the spectrum. Strong intramolecular hydrogen bonds exist in 3-nitro-4-hydroxyisoquinoline and 3-piperidinomethyl-4-hydroxyisoquinoline.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1535–1539, November, 1971
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Zaitsev, B.E., Andronova, N.A., Dyumaev, K.M. et al. IR spectra and structures of 3-hydroxyquinoline, 4-hydroxyisoquinoline, and their derivatives. Chem Heterocycl Compd 7, 1429–1432 (1971). https://doi.org/10.1007/BF00481112
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DOI: https://doi.org/10.1007/BF00481112