Zur konformation geschützter aminosäuren—I: NMR-untersuchungen von t-BOC-glycin |
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Authors: | M Branik H Kessler |
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Institution: | Institut für Organische Chemie der Universität, D-6 Frankfurt (M), Theodor Stern Kai 7 Germany |
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Abstract: | Z, E-Isomerism of the urethane bond of t-BOC-glycine was observed by 1H- and 13C-NMR spectroscopy at various temperatures in several solvents. The special stabilization of the Z isomer at low temperatures in CDCl3 has been explained by intra- and intermolecular H-bond forming a 7-membered ring. Thermodynamic data have been determined for the ground state (AH°= ?7 kcal/mol, Δ° = ?25 Clausius) as well asfor the barrier of interconversion (ΔG° = 15·4 kcal/mole for the deuterated title compound) in CDCl3. The equilibrium between the Z and the E conformation is shifted towards the E conformation in more polar solvents (acetonitril-d3, acetone-d6, DMSO-d6), in which cyclization of the Z conformation is not important. |
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