Ionisation characteristics and elimination rates of some aminoindanones determined by capillary electrophoresis

Capillary electrophoresis (CE) has emerged as an important tool for evaluating the ionisation characteristics of compounds and their corresponding pKa values. A particular strength of CE in this context is that its relative selectivity allows one to measure the extent of ionisation of materials that are impure. In this study, using CE, we have measured the pKa values of a series of anti-inflammatory aminoindanones, which underwent degradation to indenone during the course of the determination. We subsequently monitored the elimination reactions measuring remaining indanone over the pH range 2.6–10 at constant ionic strength and temperature. The decomposition of the tertiary amino derivatives was especially fast with first-order half-lives of less than 10 min observed at pH 7.4. The resulting sigmoidal pH rate profiles can be accounted for by assuming unimolecular elimination of the protonated (slow) and neutral (fast) forms of the amines. This study provides further support for the use of CE in evaluating amino ionisation especially in cases where degradation might be expected.