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.
Read more about this topic: Nitrogen Inversion
Famous quotes containing the words energy and/or barrier:
“Since the beginning of time, three-quarters of the mental energy and of the lies inspired by vanity have been expended for their inferiors by people who are only abased by such expenditure. And Swann, who was easygoing and unaffected with a duchess, trembled at the thought of being scorned and put on airs when he was with a housemaid.”
—Marcel Proust (1871–1922)
“Clearly, some time ago makers and consumers of American junk food passed jointly through some kind of sensibility barrier in the endless quest for new taste sensations. Now they are a little like those desperate junkies who have tried every known drug and are finally reduced to mainlining toilet bowl cleanser in an effort to get still higher.”
—Bill Bryson (b. 1951)