The solubility of phenol in water is about 0.9 M. One might thus argue that NDIS experiments requiring for sufficient resolution molar aqueous solutions should not be feasible, nevertheless, we have found that in the presence of a 3 m solution of TMACl, the solubility of phenol increases to about 3 m. This is presumably due to the favorable TMA-phenol interaction, consistent with the use of quaternary ammonium salts in deep eutectic solvent extraction for aromatic species. As expected, prosECCo75 reproduces this behavior by keeping phenol dissolved (Fig. and Fig. ), whereas CHARMM36 exhibits more extensive phenol aggregation (Fig. and Fig. ).Similarly to TMA-pyridine, CHARMM36 leads to a more pronounced headphone-like arrangement favoring TMA interaction with the rings electronegative hydroxyl motif. However for the remaining aromatic ring, the face-on cation-π interaction is significantly stronger for prosECCo75 than CHARMM36(Fig. and Fig. ). Similarly to the case of pyridine, we can use these simulations to predict the correlations between H TMA and H Ph (Fig. ), which show even more clearly the strengthening of cation-π interactions upon charge scaling, to be tested by the above mentioned upcoming neutron scattering measurements. These experiments will further assess the reliability and versatility of prosECCo75, the accuracy and robustness of which is grounded in the physically well justified ECC scaling approach. Finally, we note that the positive effect of charge scaling on the accuracy of the description of cation-π interactions involving TMA is to some extent surprising. Indeed, our previous studies have demonstrated that the effect of ECC on the strength of ion pairing in aqueous solutions diminishes with decreasing charge density, becoming rather weak for ions like TMA. The present work shows that this is not true for cation-π interactions, where accounting for electronic polarization via charge scaling helps to establish the right balance between electrostatic and hydrophobic forces.