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Unformatted text preview: Chiral tetravalent ammonium salts (quaternary ammonium salts) display stereochemical features similar to chiral tetravalent carbon. Interconversion of enantiomers requires bond breaking. N : R' R'' R''' fast N : R' R'' R''' interconversion of amine enantiomers by fast inversion at the nitrogen center When there are three different groups attached to the nitrogen, the structure is chiral . But because of very fast inversion at the stereocenter (the inversion rate in NH 3 is close to 10 11 s-1 ), it is not possible to resolve a chiral amine . N R' R'' R''' N R' R'' R''' X R R + + chiral quaternary ammonium salts can be resolved C R' R'' R''' C R' R'' R''' X R R chiral carbon compounds can be resolved...
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