Because of the nonpolarizable nature of class 1 and class 2 IPs, the per-atom partitioning of the quantum mechanical electron density significantly influences simulation results. There are large differences in the relative polarizations of the oxygen and nitrogen atoms in different IPs from simulation literature of PEO-LiTFSI, with no clear justification for variations across studies. To identify a chemical explanation for these vastly different polarization states of TFSI, we performed DBSCAN clustering 28,29 using SciKitLearn 30 on all of the LiTFSI geometries obtained from trajectories obtained using a previously-trained ether ionic liquid Neural-Network Molecular Dynamics (NNIPMD) 31 model according to the lithium to anion negative atom (O, N, F) distances. The results of this clustering are seen in Figure , where each cluster of geometries was found to represent a different Li-TFSI coordination mechanism as noted by the molecular visualizations in Figure . The AuTo+O and AuTo+N charges are the average charges of all NNIPMD geometries corresponding to each respective coordination mechanism. and the nitrogen-coordinating mechanism (AuTo+N). DFT studies show the lowest-energy nitrogen-coordinating geometry is 13.76 kcal/mol higher in energy than the lowest oxygencoordinating geometry. c) Plot of charge partitioned onto the nitrogen and oxygen in TFSI for the investigated interatomic potentials. Note that all charges have been scaled such that the TFSI anion has a net charge of 0.7.