Given the well-established importance of carboxylic acids in governing reactivity and imparting selectivity in these asymmetric oxidation reactions, we first sought to understand which structural features of these co-ligands underpin performance. Therefore, an extended array of carboxylic acids differing in electronic and structural properties were tested by taking the previously investigated oxidation of N-cyclohexylpivalamide (S1) catalyzed by [Mn(OTf)2( TIPS mcp)] (mcp = N,N′-dimethyl N,N′-bis(2pyridylmethyl)-1,2-trans-diamino cyclohexane) as the model reaction. As depicted in Figure , the yield of N-(3-oxocyclohexyl)pivalamide (P1) oxidation product is markedly affected by acid choice, resulting in yields ranging from 0 to 90%. Enantioselectivities also span a relatively wide range (33-86% ee), but are prominently clustered towards moderately high values (78-86% ee). Observing this clustered output, we chose to deploy classification algorithms to identify which features correlate with performance. Towards this goal, molecular features were collected by initially performing a conformational search on each of the carboxylic acids using Macromodel; each To account for the parameters derived from the most populated conformers, all descriptors from DFT-computed conformers were Boltzmann-averaged at 233 K based on their relative energies. Additionally, using the collection of conformers the maximum, minimum, and low-energy-conformer values for each descriptor were extracted, generating a library of over 600 molecular descriptors (See workflow in the Supporting Information, Scheme S1).