Intramolecular interactions in aromatic series: IV.* Molecular orbital structure of some aromatic derivatives of VIA group

S. A. Krupoder, G. N. Dolenko, B. G. Zykov, G. G. Furin, N. F. Salakhutdinov, O. Kh Poleshchuk

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    Abstract

    A study was carried out by means of X-ray emission and photoelectron [He(I)] spectroscopy on the electronic structure of pentafluoro derivatives of anisole, its thio and seleno analogs and sulfides of C6F5SX type [X = CHF2, CF(CF3)2]. Photoelectron spectra were measured and interpreted proceeding from calculations by PM3 method, π-fluoroeffect, and relative intensities of He(I) bands. The results of investigation show that the upper occupied levels virtually contain no contributions from molecular orbitals of oxygen, sulfur, and selenium. On replacing the methyl group with perfluorinated alkyls the efficiency of interaction between the unshared electron pairs of these elements with the π-system of the benzene ring is reduced. The replacement of sulfur and selenium for oxygen results in negligible shift of the bands corresponding to π-MO indicating the weak effect on the electronic structure of the related compounds at substituting one chalcogen for another.

    Original languageEnglish
    Pages (from-to)553-559
    Number of pages7
    JournalRussian Journal of Organic Chemistry
    Volume36
    Issue number4
    Publication statusPublished - 1 Apr 2000

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    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Krupoder, S. A., Dolenko, G. N., Zykov, B. G., Furin, G. G., Salakhutdinov, N. F., & Poleshchuk, O. K. (2000). Intramolecular interactions in aromatic series: IV.* Molecular orbital structure of some aromatic derivatives of VIA group. Russian Journal of Organic Chemistry, 36(4), 553-559.