It is well understood that stacking is mostly driven by dispersion interactions, and AmberFD is able to capture this balance for both the examples shown in Figure and the remaining stacked profiles used in the fitting procedure (see Supporting Information). Consequently, while H-bond profiles agreed very nicely with QM polarization and charge transfer, the induction energy is not as well reproduced when put in the stacked configuration. We attribute this deficiency from the nature of polarization being accounted for by changes in charge populations alone, as a perfectly planar molecule would not be able to induce any dipole moments orthogonal to this plane. This is not a problem though, as E pol and E ct are much smaller compared to the total frozen energies which are driven mostly by E disp and E Pauli . Rather, the shape of the profile is more important, and previous works have demonstrated that the overestimated steepness at short intermolecular distances is a known artifact of r -12 based force fields that can greatly effect stacking in simulations. Both E int and E frz AmberFD profiles share minimum energies only a few kJ/mol off from their QM partners, and the locations of these minimums are also share similar positions.