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Journal of Applied Spectroscopy

, Volume 85, Issue 1, pp 9–20 | Cite as

Rotational Isomers, Intramolecular Hydrogen Bond, and IR Spectra of o-Vinylphenol Homologs

  • V. P. Glazunov
  • D. V. Berdyshev
  • N. N. Balaneva
  • O. S. Radchenko
  • V. L. Novikov
Article
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The ν(OH) stretching-mode bands in solution IR spectra of five o-vinylphenol (o-VPh) homologs in the slightly polar solvents CCl4 and n-hexane were studied. Several rotamers with free OH groups were found in solutions of o-VPh and its methyl-substituted derivatives in n-hexane. The proportion of rotamers in o-VPh homologs with intramolecular hydrogen bonds (IHBs) O–H...π varied from 22 to 97% in the gas and cyclohexane according to B3LYP/cc-pVTZ calculations. The theoretically estimated effective enthalpies –ΔH of their IHBs varied in the range 0.20–2.24 kcal/mol.

Keywords

o-vinyl-, o-propenyl-, and o-butenylphenols IR spectrum ν(OH) stretching-mode bands density functional rotamer intramolecular hydrogen bond, enthalpy 
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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • V. P. Glazunov
    • 1
  • D. V. Berdyshev
    • 1
  • N. N. Balaneva
    • 1
  • O. S. Radchenko
    • 1
  • V. L. Novikov
    • 1
  1. 1.G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of SciencesVladivostokRussia

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