Solubility of Mono-Aminoacridines

Solubilities of mono-aminoacridines (AAs) in a variety of solvents were studied computationally using COSMO-RS method and selectively confirmed by experiment (liquid chromatography and gravimetry). The results confirm the reliability of COSMO-RS for ranking solvents on the basis of dissolving a specific AA, but not ranking the solubilities of different AAs in the same solvent. Pyrrolidine and some pyrrolidine-based mixtures were predicted to deliver outstandingly high solubilities of AAs (10-30 % by mass, depending on the compound). Hydrogen bonding was found to have a considerable role in the solubility of AAs, which can act as hydrogen bond donors and acceptors. The obtained data and conclusions can facilitate solvent selection for purification of AAs, sample preparation for MALDI-MS if an AA is used as a matrix, and can be helpful for solubility-related applications involving other compounds.