The oligothioetheramide (oligoTEA) family is a novel set of synthetic macromolecules with the advantageous characteristic of sequence-specificity. Due to their abiotic and highly modular nature, oligoTEAs are currently being explored in a variety of biological applications, ranging from use as antibacterial and antiviral agents, to use as heteromultifunctional cross-linkers and cell penetrating agents. The problem of endosomal escape in intracellular drug delivery represents an arena where this family of macromolecules may find potential use. Here, I report initial investigations into the physiochemical properties of oligoTEAs that would be relevant in tackling such a problem. Together, these methods and results can form the basis for future rational design of an oligoTEA endosomal escape agent. pKa and hydrophobicity are two key parameters routinely used in assessing the viability of new drug delivery candidates. From partitioning data, bulk microscopic measurements of pKa and hydrophobicity were determined for a library consisting of oligoTEAs of differing length and backbone composition. Using standard regression techniques as well as tools from equilibrium statistical mechanics, these measurements are used to address the possibility for correlations (1) between whole oligomers and their constituent parts (2) between backbone components and side-chain groups and (3) between neighboring side-chain groups. In doing so, some heuristics are uncovered that will be useful in navigating the oligoTEA design space.