Mechanistic studies on the hydrolysis of a dimeric alkylzinc bis(2-pyridylmethyl)amide

The hydrolysis of a dimeric alkylzinc amides surprisingly leads to exchange of the amido ligand by a hydroxo group. Based on the pKa values, one would instead expect the formation of an alkane. DFT investigations of the reaction pathways clearly demonstrate the importance of N-H-O bridges during the formation of transition structures.