Trivalent nitrogen compounds

The answer is both yes and no. Yes in principle, but no in practice. Trivalent nitrogen compounds undergo a rapid umbrella-like inversion that inter-converts enantiomers. We therefore can t isolate individual enantiomers except in special cases. 

Pyramidal inversion (Section 24.2) The rapid stereochemical inversion of a trivalent nitrogen compound. 

In the first section of this paper, we discussed Werner s views of the structure of trivalent nitrogen compounds. We shall now consider briefly... 

Betweeu 1890 and 1893, Werner produced the three most important theoretical papers of his career. His doctoral dissertation (1890, cowritten with his teacher Arthur Hantzsch), a true classic of science writing on the topic of stereochemistry, extended Joseph Achille Le Bel and Jacobus Hen-ricus van t Hoffs concept of the tetrahedral carbon compound (1874) to the nitrogen compound. It explained many puzzling paradoxes of geometrically isomeric, trivalent nitrogen compounds and placed nitrogen compound stereochemistry on a firm theoretical basis. 

Trivalent nitrogen compounds are also approximately tetrahedral in shape. In this case, however, the barrier to inversion is small and the compounds cannot be separated as pure enantiomers at normal temperatures. 

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