Relation between activity and selectivity in electrophilic substituents in five-membered heteroaromatic compounds. 3. Electronic effects of substituents

  • L. G. Gorb
  • I. M. Morozova
  • L. I. Belen'kii
  • I. A. Abronin
Physical Chemistry
  • 18 Downloads

Conclusions

  1. 1.

    By the semiempirical SCF MO LCAO method in a CNDO/2 valence approximation we have carried out calculations for a series of monosubstituted benzenes, pyrroles, furans, and thiophenes and their C-protonated forms.

     
  2. 2.

    On the basis of a correlation of theoretical and experimental reactivity indexes, we have drawn some conclusions about the different transfer of substituent electron effects to theα- andβ-positions of five-membered heteroaromatic rings.

     
  3. 3.

    We have shown that orbital interaction calculations are necessary to explain the selectivity of the electrophilic reactions of the five-membered heterocycles.

     

Keywords

Pyrrole Thiophene Electrophilic Reaction Heteroaromatic Compound Monosubstituted Benzene 

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Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • L. G. Gorb
    • 1
  • I. M. Morozova
    • 1
  • L. I. Belen'kii
    • 1
  • I. A. Abronin
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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