Abstract
The electronic structure ofo-methoxy(hydroxy)-substituted benzenes has been investigated by the combined use of photoelectron spectroscopy and molecular orbital calculations by means of the semi-empirical AM1 method. Absorption bands in the PE spectra have been assigned, the dependence of someπ-orbital energies on the molecular conformation has been found, and the estimation of the mean torsion angle of the OCH3-group with the plane of the benzene ring has been carried out. The results obtained show that the gas-phase conformations of the heavy-atom framework of guaiacol and vanillin molecules are planar. For veratrole and veratraldehyde, nonplanar conformations with mean torsion angles ϕ ≈ 80° and 55°, respectively, have been observed.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1757–1760, October, 1993.
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Vokin, A.I., Frolov, Y.L., Medvedev, S.A. et al. Conformations of methoxy(hydroxy)-substituted benzenes and benzaldehydes in the gas phase. Russ Chem Bull 42, 1680–1683 (1993). https://doi.org/10.1007/BF00697039
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DOI: https://doi.org/10.1007/BF00697039