The nickel pincer nucleotide (NPN) cofactor is used by a superfamily of α-hydroxyacid racemases and epimerases via a hydride transfer (HT) mechanism. The most well-studied of these enzymes is lactate racemase, responsible for interconversion of L- and D-lactate. The cofactor is a Nickel complex of an SCS pincer ligand has been proposed to mediate HT at the C-atom that is coordinated to the Ni center. Direct structural or spectroscopic evidence to support the proposed hydride intermediates and reaction mechanism for isomerization are limited at this time. In this talk I will describe synthesis and reactivity of SCS-Ni pincer complexes supported by a pyridinium bis(thioamide) ligand. I will also discuss the isolation and characterization of both 1,2- and 1,4-dihydropyridinate (DHP) complexes that were obtained via HT reactions with the SCS-Ni model compounds. The 1,4-DHP nickel model compound provides first direct experimental evidence to support the formation of a 1,4-DHP in the proposed mechanism of LarA. The effects of ligand protonation state on the reactivity of the complexes are also examined, along with preliminary HT reactivity studies and their relationship to the thermochemistry of the ligand-based hydrides.