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Chemical Shift Nonequivalence of Diastereotopic Protons Due to Restricted Rotation around Aryl-Nitrogen Bonds in Subsituted Amides.


AD660486

Publication Date 1967
Personal Author Shvo, Y.; Taylor, E. C.; Mislow, K.; Raban, M.
Page Count 10
Abstract Chemical shift nonequivalence of diastereotopic protons in cyclic and acyclic amides and several related systems is interpreted within the framework of the conformational analysis of mobile systems. An approach to a critical discussion of kinetic and thermodynamic restrictions on ring flipping, torsional, and inversional modes of conformational interchange is developed. The possibility of cisoid-transoid isomerism about the nitrogen-carbonyl bond is discussed, and assignments of configuration of the s-cis isomers of N-benzyl-N-(o-tolyl) formamide were made, using aromatic solvent-induced shifts. (Author)
Keywords
  • Nuclear magnetic resonance
  • Stereochemistry
  • Amides
  • Molecular isomerism
  • Reaction kinetics
  • Thermodynamics
  • Chemical bonds
  • N-heterocyclic compounds
  • Acetamides
  • Formamides
  • Ketones
  • Aromatic compounds
  • Reprints
  • Benzyl tolyl acetamides
  • Benzyl tolyl formamides
  • Tolyl dihydroisoquinolinones
NTIS Subject Category
  • 99F - Physical & Theoretical Chemistry
  • 99D - Basic & Synthetic Chemistry
Corporate Authors Princeton Univ N J Dept of Chemistry
Supplemental Notes Prepared in cooperation with Tel-Aviv Univ. under grant CA-02551.
Document Type Journal Article
NTIS Issue Number 196724
Chemical Shift Nonequivalence of Diastereotopic Protons Due to Restricted Rotation around Aryl-Nitrogen Bonds in Subsituted Amides.
Chemical Shift Nonequivalence of Diastereotopic Protons Due to Restricted Rotation around Aryl-Nitrogen Bonds in Subsituted Amides.
AD660486

  • Nuclear magnetic resonance
  • Stereochemistry
  • Amides
  • Molecular isomerism
  • Reaction kinetics
  • Thermodynamics
  • Chemical bonds
  • N-heterocyclic compounds
  • Acetamides
  • Formamides
  • Ketones
  • Aromatic compounds
  • Reprints
  • Benzyl tolyl acetamides
  • Benzyl tolyl formamides
  • Tolyl dihydroisoquinolinones
  • 99F - Physical & Theoretical Chemistry
  • 99D - Basic & Synthetic Chemistry
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