Abstract
The changes in 13C chemical shifts for the structural change R 2NH → R 2NLi have been measured for a series of dialkylamines. These lithiation shifts are largest at the alpha carbon (3.7 – 9.7 ppm) and decrease in the order α > β > γ > δ. The rates of lithium-hydrogen interchange between R 2NH and R′ 2NLi have been determined. The activation energies are large (9 – 17 kcal/mole) and increase as the size of R or R′ increases. The slow exchange permits the direct measurement of acidity differences between pairs of amines using 13C nmr.
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