Conjugation effects. 12. Electronic structure of alkyl phenyl sulfides, sulfoxides, and sulfones

  • V. M. Bzhezovskii
  • G. N. Dolenko
  • G. A. Kalabin
  • V. A. Topchii
  • I. A. Aliev
  • G. K. Parygina
  • B. A. Trofimov
Physical Chemistry
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Conclusions

  1. 1.

    The p,π conjugation of unshared electron pairs of the heteroatom with the π system of the benzene ring has a determining influence on the distribution of the ir-charge density in alkyl phenyl sulfides. Acceptor IR interaction of the S atom with the unsaturated fragment plays a significant role only in some alkyl phenyl sulfoxides and sulfones.

     
  2. 2.

    Increasing branching of the alkyl substituent in the order Me, Et, i-Pr, and t-Bu leads in the alkyl phenyl sulfides to a change in the steric interactions alkyl-benzene ring, as well as to a deterioration of thep,π conjugation of the S atom with the aromatic fragment, due to disturbance of the coplanarity of the molecules. In the alkyl phenyl sulfoxides and sulfones the induction and resonance interaction of the SOR and S02R groups with the ring remains practically unaffected.

     

Keywords

Sulfone Benzene Sulfoxide Benzene Ring Electron Pair 

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Literature cited

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Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • V. M. Bzhezovskii
    • 1
    • 2
    • 3
    • 4
  • G. N. Dolenko
    • 1
    • 2
    • 3
    • 4
  • G. A. Kalabin
    • 1
    • 2
    • 3
    • 4
  • V. A. Topchii
    • 1
    • 2
    • 3
    • 4
  • I. A. Aliev
    • 1
    • 2
    • 3
    • 4
  • G. K. Parygina
    • 1
    • 2
    • 3
    • 4
  • B. A. Trofimov
    • 1
    • 2
    • 3
    • 4
  1. 1.Irkutsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRUSSR
  2. 2.A. A. Zhdanov Irkutsk State UniversityUSSR
  3. 3.Kiev Polytechnic InstituteUSSR
  4. 4.S. M. Kirov Azerbaidzhan State UniversityBaku

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