Acetylacetone and related 1,3-diketones
condense with primary alkyl- or aryl
amines resulting in replacement of the
carbonyl oxygen atoms with NR groups, where R =
aryl,
alkyl. To prepare 1,3-diketimines from
bulky amines, e.g.
2,4,6-trimethylanilines, prolonged reaction times are required.
2,6-Diisopropylaniline is a common bulky building block.
Deprotonation of HNacNac compounds affords anionic
bidentate ligands that form a variety of
coordination complexes. Some derivatives with large
R groups can be used to stabilize low valent
main group and
transition metal complexes. Unlike the situation for the
acetylacetonates, the steric properties of the coordinating atoms in NacNac− ligands is adjustable by changes in the R substituent. Attachment to a metal center is usually carried out by initial deprotonation of HNacNac with
n-butyllithium; the lithium derivative is then treated with a metal chloride to eliminate
lithium chloride. In some cases, HNacNacs also serve as charge-neutral 1,3-diimine ligands. File:FUYTEAfragment.png|thumb|left|Structure of [(C6H3-2,6-(i-Pr)2)2NacNac]NiSCPh3 viewed down the C2 axis, illustrating the steric bulk of this NacNac ligand (CPh3 removed for clarity). Color code=gray = C, white = H, blue=N, yellow=S, green=Ni). ==Related NacNac ligands==