The dipp DAMN ligand was synthesised as a slightly air-sensitive white solid in three steps from 2,7-dimethyl-1,8-naphthyridine in a 32% yield (see ESI section 1.2). A reaction of dipp DAMN with 2 equiv of Mg(n-Bu)2 (Scheme 2), resulted in clean formation of 1 as a brown solid which was isolated in quantitative yield. The number of resonances in 1 H-and .302(4)-2.321(4) Å) are in line with the metrics of crystallographically characterised Mg 2-alkyl2 species with a similar "diamond-core". The Mg-C bond lengths are slightly longer than in most of these structures, likely due to the coordination of THF and the resulting higher electronic saturation of the Mg-centres. The bond lengths of Mg1-N3 and Mg2-N4 (2.022(3) and 2.020(4) Å respectively) are considerably shorter than the Mg1-N1 and Mg2-N2 bonds (2.247(3) and 2.220(3) Å respectively), which is in line with their higher anionic character. Having isolated and characterised 1, we set out to investigate follow-up reactivity of this compound. Ligated alkylmagnesium complexes are frequently used as a springboard towards Mg-H complexes that feature rich reactivity with a variety of substrates. These hydrides are typically accessed by treating the alkylmagnesium species with PhSiH3, forming the hydride and PhSiH2R through σ-bond metathesis. Treating C6D6 solutions of 1 with PhSiH3 or H2 (1 bar) at room temperature (RT) gave no conversion (see ESI figures S14-S15). Only upon heating the mixtures to reflux for multiple hours was conversion observed, resulting in intractable mixtures. To gain a better understanding of the relative inertness of 1 at RT we investigated its electronic structure using DFT calculations. Specifically, we calculated the Fukui function (𝑓𝑓 -) to gain insights into the nucleophilic loci. These calculations (Figure ) revealed that the nucleophilic loci reside on the N-donors of the pendant amines. In order to see how these observations compare to other systems, we extended our calculations to representative dinuclear and mononuclear (both solvated and unsolvated) complexes from literature. For the dinuclear [ dipp NacNacMg(μ-(n-Bu))]2 complex we obtained similar ligand-based loci, found on the NacNac nitrogen donors and the methine carbon of the ligand backbone. Notably, in contrast to the observations for the dinuclear complexes, we found additional contributions of 𝑓𝑓 - on the α-carbon of the n-Bu -ligands for the mononuclear (unsolvated and THF-solvated) analogues complexes bearing the same dipp NacNac ligand. Calculation of the atomic charges in 1 through natural population analysis (NPA) revealed that the bonding between the Mg-centres and the dipp DAMN and n-Bu -ligands is best described as highly ionic, with the charges found on the Mg-centres being +1.752 and +1.745. Similarly, we found highly ionic bonding for the three literature complexes, with a nuanced trend of decreasing ionic character being observed when moving from the dinuclear complexes to the mononuclear analogues (1 > [ dipp NacNacMg(μ-(n-Bu))]2 > dipp NacNacMg(n-Bu)THF > dipp NacNacMg(n-Bu)). We propose that the bridged binding mode of n-Bu -in the dinuclear complexes distributes the charge effectively over the Mg-C-Mg motif, rendering it less nucleophilic than in the mononuclear analogues. Beyond these thermodynamic considerations there are also kinetic factors that contribute to the relative inertness of 1. One of these factors is the appreciable steric crowding around the Mg-centres in these dinuclear complexes. Additionally, the absence of open coordination sites for reagents to (pre)coordinate levies a kinetic barrier that can hamper reactivity. In contrast with the dimeric system, the rigid and dinucleating nature of the ligand in 1 disfavours "monomerisation" (i.e. displacing a Mg-centre out of the ligand pocket). This was confirmed using a relaxed potential energy scan of the system where the Mg-Mg distance was increased (see ESI figure ). A penalty of 30.0 kcal•mol -1 on the electronic energy was obtained upon a 2 Å increase, with the trend propagating upon further increase. We envisioned that an open coordination site could be achieved instead upon displacement of a THF ligand. Dissociation of THF in gas-phase calculations was found to be energetically uphill (ΔG = 5.6 kcal•mol -1 , see ESI section 2.7) but accessible. As such we tested our hypothesis using a protic substrate that can displace THF and coordinate to the Mg-centres. H-NMR analysis off a C6D6 solution of 1 with 1 equiv of t-BuOH revealed partial conversion of 1 and the formation of butane (for more insights regarding the speciation at this stage, see ESI section 1.6). Addition of a second equivalent pushed the reaction to completion, with a C2v-symmetric species being majorly observed in the 1 H-NMR spectrum (see ESI figures S16-18). All observed resonances are slightly shifted with respect to 1 and the butyl resonances are lost. Additionally, a singlet arises at δ = 1.15 ppm that integrates to 18H, indicative with the formation of bis-t-butoxide species 2. Addition of more equiv of t-BuOH to 2 led to decomposition and the high solubility of 2 in apolar solvents precluded obtaining 2 as an analytically pure compound and obtaining a single crystal for structure elucidation by X-ray diffraction analysis. This reactivity shows that 1 can react readily with coordinating substrates at room temperature. This observation prompted us to explore the reactivity of 1 in the aforementioned amine-borane dehydrogenation chemistry reported by the Harder group. The addition of 2 equiv of i-PrNH2•BH3 to a solution of 1 in C6D6 at 25 °C resulted in a dark purple mixture. H-NMR analysis of the mixture after 10 minutes revealed full conversion of both starting materials to a mixture of species and concomitant liberation of butane (see ESI section 1.7). Based on the aromatic region of the spectrum, two C2v-symmetric species are formed in a 1:2 ratio but the spectrum does not allow for further identification of resonances belonging to these species. To our surprise, we observed the presence of H2 (δ = 4.47 ppm) in solution already at 25 °C. Spielmann et al. showed that mononuclear NacNac magnesium complexes display this reactivity at 90-110 °C, and that the corresponding dinuclear analogues enable this at lower temperatures (60-90 °C). After the solution was left to stand overnight at ambient temperature, a plethora of resonances was observed in the δ = 4.5-6.0 ppm region. The 11 B-NMR spectrum (see ESI figure ) after addition shows resonances at δ = -20.3, -6.8, 1.3 and a broad resonance at 28.3 ppm. After overnight at ambient temperature, the middle two resonances decreased in intensity and an additional broad resonance at 32.2 ppm appeared. Based on literature, the broad resonance at δ = 28.3 and the sharper resonance at -20.3 ppm can be attributed to the -BH and -BH3 protons respectively of the BH3 adduct of the bora-amidinate ligand we propose for 3 in Scheme 3 (see ESI section 1.7 more detail). Observation of the bora-amidinate suggests that the dehydrocoupling of the amine-borane proceeds through the BNBN mechanism found in literature for the bis-NacNac complexes reported by the Harder group but also for alkali metal amidoboranes (see Scheme 4). The detection of H2 at 25 °C implies that the enforced proximity of the Mg-centres imposed by the rigid dipp DAMN ligand renders the initial β-hydride elimination depicted in Scheme 4 more facile than for the more flexible dimagnesium bis-NacNac complexes, where this was only observed at 60°C for the most reactive complex.