Ionic liquids based on biocompatible ions such as amino acids are of significant interest since they offer access to a lower-cost and lower-toxicity family of green solvents for industrial processes. We have previously investigated a set of ionic liquids based on a standard cation paired with anions based on glycine, alanine, and serine, in order to understand the structural aspects of the liquid state, and highlight key interactions present in these systems. We found interesting, strong correlations between anions in the system, with a stronger degree of association than would normally be seen.Here we aim to study ionic liquids using the same trio of amino acid anions, but paired with a weaker, less-associating cation in order to further push the structural association of anions in the system, and probe the reasons behind observed changes in trends of physicochemical properties.