Nitrogen Inversion - Energy Barrier Considerations

Energy Barrier Considerations

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.

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