) are most surface active. Similar to the surface tension measurements, small differences in the logKOW or logKOAS values between diastereomers were also noted. With the exception of the diacid ester dimers (i.e., compounds 16 and 21), the least surface active pair in our suite, the diastereomers of mixed chiral origin derived from both (+)-and (-)-a-pinene (red and blue balls), showed slightly more positive logKOAS and logKOW values than their counterparts derived from a single enantiomer of a-pinene (red or blue balls). The largest difference for both the logKOAS (0.5±0.01) and logKOW (0.4 ± 0.01) values was seen between the aldehyde acid dimer diastereomers (i.e., compounds 14 and 19). Studies of synthetic polymers have shown that changes in tacticity can alter the hydrophilicity of the polymer, and we assert a similar phenomenon may help to explain the difference in surface activity between the diastereomers studied here. This effect may be of even greater importance when considering higher order oligomers, where increased opportunity for structural variability may lead to larger differences in hydrophobicity.