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

Journal of Chromatography. a
Ana Luísa SimplícioJohn M Clancy

Abstract

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.

References

Jan 19, 1999·Journal of Chromatography. B, Biomedical Sciences and Applications·P CoufalM Webb
Jun 24, 2000·Journal of Chromatography. a·P BartákR Vespalec

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Citations

Jan 2, 2007·International Journal of Pharmaceutics·Ana Luísa SimplícioJohn F Gilmer
Mar 1, 2005·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·John F GilmerJohn M Clancy
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Tao ZhangHelen Sheridan

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