Figure shows that the relative surface tension depression differences seen across our suite of diastereomeric pairs is quantifiable and, in many cases, the magnitude of the observed difference is significant. In each case, the dimeric adducts derived from opposite enantiomers of α-pinene show a greater surface tension depression than their diastereomer counterparts. For all compounds, the difference between diastereomeric pairs exceeds the error in each measurement, which ranged from 0.11-0. (7) and 61.53 mN m -1 (8) (Figure ), while the ester dimers displayed variable degrees of surface tension suppression that appeared to follow a general trend with compound polarity (Figures ). The magnitude of the difference between diastereomers varies between compounds, with the largest relative difference being 6.7 ± 0.8 % between the acid-acid ester dimer diastereomers (compounds 16 and 21) (Figure ), and the smallest being 1.4 ± 0.3 % between the aldehydeketone ester dimer diastereomers (compounds 15 and 20) (Figure ). Repeating the measurements at 0.5 mM in pure water gave the same trend, with some deviations at lower concentrations (see Supporting Information Figure ).