In the present study, we aimed to identify regions of chemical space where parameterization differences between force fields lead to different optimized geometries for small drug-like molecules in the gas phase. Geometric differences between force fields for some molecules would indicate that the underlying force fields describe the molecule differently, and thus are indicative of force field differences. Here, a subset of molecules from the eMolecules database was used as a broad sample of small molecule chemical space. Five energy minimizations were performed on each molecule using one of five force fields: GAFF, GAFF2, MMFF94, MMFF94S, and the Open Force Field Initiative's SMIRNOFF99Frosst . Two geometric measurements, Torsion Fingerprint Deviation (TFD) and TanimotoCombo , were used to better identify meaningful geometric differences that may suggest parameterization inconsistencies.