Low-valent main group compounds have long been considered as lab curiosities of limited stability and accessibility. However, research endeavors in the past three decades have changed this assumption and impressively demonstrated that species with most unusual bonding situations and electronic structures can be isolated and most importantly be applied in the activation of small molecules and strong bonds. This has sparked interest in applying such compounds also in catalysis, with the prospect of developing sustainable, transition metal free alternatives to existing protocols. One of the most researched classes of low valent main group compounds applied in small molecule activation are carbenes and their heavier congeners, R-E-R' (E = C-Pb). This interest was particularly fueled by the landmark report by Bertrand and coworkers in 2007 showing that alkyl(amino)carbenes (e.g. B, Figure ) are able to activate dihydrogen at mild temperatures, a transformation long thought to be exclusive to precious transition metals such as palladium, rhodium, iridium (e.g. A) or ruthenium. This transition-metal like behavior is enabled by the availability of an energetically high lying lone pair in a non-bonding orbital and a low-lying vacant orbital at the group 14 element, a feature reminiscent of the often partially filled d-orbitals of the transition metals. With the motivation to substitute these transition metals in future hydrogenation reactions, vast research efforts have focused on the expansion of hydrogen activation to other carbenes as well as their heavier congeners. Investigations of the use of different substitution patterns and their impact on the H2 activation capability led to a first understanding of the important electronic properties. For example, it has in general been accepted that a small HOMO-LUMO and small singlet-triplet energy gap enhance the activity of the divalent group 14 compounds towards bond activations. Owing to the increased stability of the +2 oxidation state within the group, the activity decreases from carbon to lead. Thus, also several acyclic silylenes and few germylenes have been reported to undergo H2 activation at the group 14 element center (Figure ). However, for establishing catalytic protocols not only the kinetic but also the thermodynamic profile for H2 activation needs to be considered to enable H2 transfer at mild conditions. Thus, no carbene system has been identified yet, that is able to activate and transfer H2 in a similar way as it has been established since decades for the transition metals. To close this gap, the design of new tetrylenes with a specifically designed substitution pattern is required. However, the ability of silylenes/germylenes to activate H2 is difficult to predict and still not fully understood. Therefore, optimizations of the H2 activation by carbene species still relies on tedious trial-and-error experiments by varying the substitution pattern based on chemical intuition. Similar to the substitution pattern in tetrylene chemistry, the choice of ligands in transition metal complexes is decisive for their ability to function as homogeneous catalysts. To accelerate catalyst design, the quantification of the steric and electronic ligand properties has early been addressed first by experimental and later by computational methods. Based on this featurization of ligands improved ligand and catalyst structures can nowadays be predicted using computational and machine learning methods and has led to remarkable advances in the past few years. While this approach has been widely used not only in transition metal and organocatalysis, but also in materials chemistry and drug design, a similar strategy has not yet been applied for the specific design of main group species. We envisioned that the field of main group element catalysis could also benefit from such an approach and the computer-aided selection and prediction of improved structures. To realize this goal, we aimed at the development of a model that allows to computationally describe and predict the propensity of tetrylenes to activate dihydrogen.