NacNac

NacNac is the name for a class of anionic bidentate ligands. 1,3-Diketimines are often referred to as "HNacNac", a modification of the abbreviation Hacac used for 1,3-diketones. These species can exist as a mixture of tautomers.

Acetylacetone and related 1,3-diketones condense with primary alkyl- or arylamines 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.

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 LiCl. In some cases, HNacNacs also serve as charge-neutral 1,3-diimine ligands.

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