All density functional theory (DFT) calculations were performed with the Gaussian 16 software using the B3LYP density functional with the def2-SVP basis set. Dispersion corrections were applied using Grimme's D3 dispersion method with the Becke-Johnson damping function. Figure shows that a core comprised of a Ni(CO)3 and PH3 phosphine system was first optimized and then AaronTools was used to functionalize the phosphine with the following groups: Me, Et, Pr, i Pr, t Bu, allyl, Ph, Bn, Cy, F, Cl, Br, I, CF3, CH2F, CH2Cl, 2,6-F-Ph, 3,5-F-Ph, NH2, NMe2, OH, OMe, SH, SMe, SiH3, SiMe3, CHO, COCH3, CONH2, COOCH3, COOH, CH2OH. All 4703 unique (R)3P-Ni 0 (CO)3 structures were then optimized in the gas-phase with B3LYP-D3(BJ)/def2-SVP. Using the SMILES string representations for each of the phosphines, more than 100 cheminformatic features were calculated using the RDKit software package. Permutation feature importance and SHAP feature values were used to condense the model down to 19 descriptors.