For the Phen and BzQuin dimers, E b correlates reasonably well with dipole cancellation: linear regression gives an R 2 of 0.517, where the fitting parameters are a = 0.8916 kJ mol -1 D -1 and b = 23.877 kJ/mol. The correlation plot of E b vs. dipole cancellation for all Phen and BzQuin dimers can be found in Figure . Correlation is better yet within homologous series, where the differences in sterics and contact area are small enough to be ignored. For the three homologous series with at least four dimers, the 106SR series has an R 2 of 0.9527, the 58SR series has an R 2 of 0.9922, and the 151SR series has an R 2 of 0.8609. The scatter plot for these three homologous series can be found in Figure in the SI. Total dipole moment, contact surface area, and dispersion were all found to correlate poorly with binding energy, but are reported for the interested reader. Numerical results for all conformers are documented in Tables , and S7. Dipole cancellation for all homodimers of Phen and BzQuin, computed at the ωB97X-V/def2-QZVPP/SMD(Toluene)//ωB97X-D4/def2-SVP/CPCM(Toluene) level of theory. Note that Phen homodimers are capable of negative dipole cancellation when charge transfer between monomers is greater than the original (small) dipoles.