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| - Control of the Conformational Equilibria in Aza-cis-Decalins: Structural Modification, Solvation, and Metal Chelation
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| - A series of amino alcohol- and diamino-cis-decalins were synthesized and their conformationalproperties investigated. The equilibrium distributions of the conformational isomers were measuredvia NMR spectroscopy. The equilibrium ratios depend on the position of the substituents on thedecalin ring system and the solvent. The 7-substituted 1-aza-cis-decalins are more likely to adoptthe N-in form than the 5-substituted analogues. The N-in form is generally favored in nonpolarsolvents, while the N-out form is favored in polar solvents. Complexation with LiClO4 and Et2Znalters the equilibrium to favor the N-in decalin conformer. Both conformers coordinate lithiumions such that “on/off” conformational switching is not observed for these decalins. Comparison ofthe results with complexation studies of (−)-sparteine allows the criteria for an ideal “on/off”conformational switch to be defined.
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