Abstract
Die Enantiomeren (M) und (P) einer Reihe verwandter aromatischer Carbonsaureamide wurden erstmals mittels Flussigkeits-Chromatographie an Triacetylcellulose analytisch untersucht und praparativ angereichert. Enantiomerenreinheiten (7–99%), spezifische Drehungen und Schwellen der Rotation um die C(sp–C(sp-Bindung (87–120 kJ/mol, Tab. 5) wurden ermittelt. Diese Energiebetrage werden im Hinblick auf den Raumbedarf von ortho-Substituenten und die Stutzeffekte durch meta-Substituenten diskutiert. The enantiomers (M) and (P) of a series of similar aromatic carboxamides have been, for the first time, investigated analytically and enriched preparatively by liquid chromatography on triacetylcellulose. Enantiomeric purities (7–99%), specific rotations, and barriers to rotation about the C(sp–C(sp bond (87–120 kJ/mol, Table 5) were determined. These energies are discussed in terms of the size of ortho substituents and of the buttressing effects by meta substituents.
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