The reactions depicted in Scheme 6 yield bicyclo[2,2,1]heptane adducts where the unsaturated substrates are added over the Ge and methine position in one NN binding pocket, while leaving the other NN pocket containing Mg unaltered. Hence, we performed analogous reactions between 2containing the same germylene motif but lacking said Mg -with an equivalent of the same unsaturated substrates. However, even at prolonged reaction times or reflux conditions no conversion of 2 was observed. The observed discrepancy in reactivity of 2 and 4 is also reproduced computationally (see ESI Table ), with addition of p-tolylacetylene over the NHGe motif in 2 being endergonic by 0.7 kcal•mol -1 , whereas the same reaction for 4d was found to be exergonic by 25.5 kcal•mol -1 and thereby suggesting that this difference is thermodynamic in nature. We hypothesise that this difference stems from the different oxidation states of the dipp NBA ligand. In 2, the ligand is reduced by two electrons, with aromaticity being retained in one of the naphthyridine rings. In contrast, no aromaticity is retained in the formally quadruply reduced ligand of 4. The combined experimental and computational data do not indicate that aromaticity is gained upon cycloaddition , but do suggest increased delocalisation of charge over the naphthyridine N-C-N motif (see ESI Figure ). We therefore propose that the majority of thermodynamic driving force originates from decreased electronic repulsion within the quadruply reduced dipp NBA ligand upon cycloaddition.