Stereogenic Nitrogen Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Stereogenic Nitrogen

A close inspection of the pseudoephedrine and ephedrine isomers suggests that other stereogenic center, the nitrogen, is present. As defined before, in shape single-bonded nitrogen is pyramidal, with the non-bonding electron pair pointing to the not occupied corner of a tetrahedral region. Its configuration is chiral because the nitrogen in these compounds is bonded to three distinct groups. The non-identical mirror-image configurations are demonstrated in the picture that is displayed below (the molecule's remainder is represented by R, and the electron pair is represented in yellow color). There would be four additional stereoisomers of pseudoephedrine and ephedrine if these configurations were stable. Though, pyramidal nitrogen is usually not configurationally stable. It fastly inverts its configuration (equilibrium arrows) by passing from a planar, sp2-hybridized transition state, leading to the mixture of interconverting R and S configurations. A 50:50 (racemic) mixture of R and S configurations would present at equilibrium if the nitrogen atom were the only chiral center in the molecule. A mixture of diastereomers will result if another chiral center is present, as in the ephedrin isomers. In any event nitrogen groups like this, if exist in a compound, do not contribute to isolable stereoisomers.

393_Stereogenic Nitrogen.jpg

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