Canadian Journal of Chemistry · 1977 · 60 citations · 0 references
Natural SciencesChemistryMolecular PhysicsOrganic ChemistrySpectroscopyConformational AnalysisConformational ChangeHeterocyclic ChemistryHeterocyclic CompoundsConformational OptimizationDouble Bond ConfigurationMacrocycle Conformation AnalysisNuclear Magnetic Resonance AnalysisNuclear Magnetic Resonance Conformational AnalysisNuclear Magnetic Resonance Structure DeterminationSteroid Ring ConformationSubstituent Effects On Conformation
The analysis of the 13 C and 1 H nuclear magnetic resonance data of 2-substituted methylenecyclohexanes and 3-substituted cyclohexenes demonstrates that a double bond stabilizes the axial conformer for an electronegative substituent. Introduction of a methoxy group on the double bond further increases the relative stability of the axial conformer. These results are interpreted in terms of the 'double bond – no bond' resonance.