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

The ν(OH) stretching-mode bands in solution IR spectra of five o-vinylphenol (o-VPh) homologs in the slightly polar solvents CCl 4 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 ro...

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Bibliographic Details
Published in:Journal of applied spectroscopy 2018-03, Vol.85 (1), p.9-20
Main Authors: Glazunov, V. P., Berdyshev, D. V., Balaneva, N. N., Radchenko, O. S., Novikov, V. L.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Atomic/Molecular Structure and Spectra
CARBON TETRACHLORIDE
CYCLOHEXANE
DENSITY FUNCTIONAL METHOD
ENTHALPY
HEXANE
Homology
HYDROGEN
Hydrogen bonds
INFRARED SPECTRA
Infrared spectroscopy
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
Isomers
Mathematical analysis
MATHEMATICAL SOLUTIONS
Physics
Physics and Astronomy
Rotational spectra
SOLVENTS
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Summary:The ν(OH) stretching-mode bands in solution IR spectra of five o-vinylphenol (o-VPh) homologs in the slightly polar solvents CCl 4 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.
ISSN:0021-9037
1573-8647
DOI:10.1007/s10812-018-0604-x