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In chemistry, a nitrogen compound like ammonia in a trigonal pyramid geometry undergoes rapid nitrogen inversion whereby the molecule turns inside out. This interconversion is a room temperature process because the energy barrier (24.2 kJ/mol) is relatively small. Contrast this to phosphine which does not show inversion at room temperature (energy barrier: 132 kJ/mol) . Even if all three substituents on the nitrogen in an amine are different, rapid inversion would prevent the nitrogen atom from becoming a permanent chiral center, since such inversion becomes effectively like a conformational change.
Additional recommended knowledge
In one study the inversion in an aziridine was slowed down by a factor of 50 by placing the nitrogen atom in the vicinity of an phenolic alcohol group compared to the oxidized hydroquinone  :
The system interconverts by oxidation by oxygen and reduction by sodium dithionite.
Categories: Amines | Physical chemistry | Stereochemistry
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Nitrogen_inversion". A list of authors is available in Wikipedia.|