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1H (1-D and 2-D) NMR spectra and the conformational states of some 3-monosubstituted saturated five-membered heterocycles

  • A. A. Panasenko
  • I. P. Baikova
  • A. A. Fatykhov
  • L. V. Spirikhin
Physical Chemistry
  • 22 Downloads

Abstract

We have recorded the1H (1-D and 2-D) NMR spectra of sulfolane, a series of 3-monosubstituted sulfolanes, and 3-acetoxy-1,1-diphenylsilacyclopentane. We have determined the chemical shifts and the proton-proton spin-spin coupling constants of seven ring protons. From analysis of the magnitudes of the vicinal spin-spin coupling constants and consideration of the full-cycle pseudorotation model for five-membered heterocycles, we found that seven conformers are most probable for 3-iodo- and 3-tert-butylsulfolanes. Four of these conformers have the half-chair conformation, three have the envelope conformation with pseudoequatorial substituents. The rest of the 3-monosubstituted sulfolanes (chloro-, bromo-, hydroxy-, and methacryloxysulfolanes) and 3-acetoxy-1,1-diphenylsilacyclopentane also have seven preferred conformations, but with pseudoaxial substituents.

Keywords

Chemical Shift Chloro Bromo Conformational State Ring Proton 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • A. A. Panasenko
    • 1
    • 2
  • I. P. Baikova
    • 1
    • 2
  • A. A. Fatykhov
    • 1
    • 2
  • L. V. Spirikhin
    • 1
    • 2
  1. 1.Institute of ChemistryAcademy of Sciences of the Moldavian SSRKishinev
  2. 2.Institute of Chemistry, Bashkir Scientific Center, Urals BranchAcademy of Sciences of the USSRUfa

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