MO Studies of Configuration and Conformation (Ⅲ). Conformations of Some 2-Substituted Furan, Thiophene and Pyrrole Carbonyl Compounds

配置와 形態에 관한 分子軌道函數論的 硏究 (第3報). Furan, Thiophene 및 Pyrrole 카르보닐 化合物의 2-置換體의 形態

  • Ikchoon Lee (Department of Chemistry, College of Science, Inha University) ;
  • Shi Choon Kim (Department of Chemistry, College of General Studies, Hanyang University)
  • 이익춘 (仁荷大學校 理科大學 化學科) ;
  • 김시준 (漢陽大學校 敎養學部 化學科)
  • Published : 1977.02.28


Conformations of nine 2-substituted furan, thiophene and pyrrole compounds have been studied by EHT methods. The preferred conformations of furan derivatives were trans form, which were mainly stabilized by electrostatic interactions. For thiophenes, electronic conjugation between the ring S and carbonyl oxygen was dominant, while for pyrroles both the electrostatic and conjugation effects were operative in determining the preferred conformations. Results of EHT calculation agreed well with experimentally determined preferences.



  1. Tetrahedron v.28 R. J. Abraham;T. M. Siverns
  2. Acta Chem. Scand. v.26 B. R. Larsen;F. Nicolaisen;J. T. Nielsen
  3. Tetrahedrom v.26 B. Rogues(et al.)
  4. Tetrahedrom v.29 S. Nagata(et al.)
  5. J. C. S. Perkin II C. L. Cheng;I. G. John;G. L. D. Ritchie;P. H. Gore;L. Farnell
  6. J. Org. Chem. v.38 A. Arsoria;S. Fisichella;G. Scarlata;D. Sciotto
  7. J. Org. Chem. v.39 A. Arsoria;S. Fisichella;G. Scarlata;D. Sciotto
  8. J. Chem. Phys. v.39 R. Hoffmann
  9. Table of Interatomic Distane and Configuration in Molecules and Ions L.E. Sutton(ed.)
  10. J. Phys. Chem. v.76 T. Drakenberg;K. Dahlqvist;S. Farsen
  11. Zh. Obs. Khimii v.44 A. S. Kuzharov (et al.)
  12. J. C. S. Perkin II L. Lunazzi;C. A. Veracini
  13. The Hammett Equation C. D. Johnson