Determination of acid-base dissociation constants of azahelicenes by capillary zone electrophoresis

J Sep Sci. 2008 Aug;31(14):2686-93. doi: 10.1002/jssc.200800227.

Abstract

CZE was employed to determine acid-base dissociation constants (pK(a)) of ionogenic groups of azahelicenes in methanol (MeOH). Azahelicenes are unique 3-D aromatic systems, which consist of ortho-fused benzene/pyridine units and exhibit helical chirality. The pK(a) values of pyridinium groups of the studied azahelicenes were determined from the dependence of their effective electrophoretic mobility on pH by a nonlinear regression analysis. The effective mobilities of azahelicenes were determined by CZE at pH range between 2.1 and 10.5. Thermodynamic pK(a) values of monobasic 1-aza[6]helicene and 2-aza[6]helicene in MeOH were determined to be 4.94 +/- 0.05 and 5.68 +/- 0.05, respectively, and pK(a) values of dibasic 1,14-diaza[5]helicene were found to be equal to 7.56 +/- 0.38 and 8.85 +/- 0.26. From these values, the aqueous pK(a) of these compounds was estimated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acid-Base Equilibrium
  • Aza Compounds / analysis*
  • Electrophoresis, Capillary / instrumentation
  • Electrophoresis, Capillary / methods
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Polycyclic Compounds / analysis*
  • Sensitivity and Specificity
  • Stereoisomerism
  • Time Factors

Substances

  • Aza Compounds
  • Polycyclic Compounds
  • helicenes