Comparison of solution chemistries of orthophthalaldehyde and 2,3-naphthalenedicarboxaldehyde

Anal Chem. 2006 Nov 15;78(22):7802-8. doi: 10.1021/ac061185g.

Abstract

Polarography was used to obtain the concentrations of the dialdehydic (10%), monohydrated acyclic (5%), and cyclic hemiacetal form (85%) of orthophthalaldehyde (OPA). For 2,3-naphthalenedicarboxaldehyde (NDA) these values were estimated to be 15, 7, and 78%. Addition of water in unbuffered solutions followed first-order kinetics with rate constants 0.0018 s-1 for OPA and 0.0012 s-1 for NDA. Dehydration to form both the dialdehyde and the monohydrate is both acid- and base-catalyzed. Both dialdehydes yield on reaction with OH- ions geminal diol anion, which is electro-oxidized to a carboxylic acid. In the most frequently used pH range for the determination of amino acids, NDA can undergo reaction with OH- ions, but OPA does not. In aqueous solutions, NDA is less strongly hydrated than OPA.

Publication types

  • Comparative Study

MeSH terms

  • Amino Acids / analysis
  • Buffers
  • Catalysis
  • Hydrogen-Ion Concentration
  • Hydroxides / chemistry
  • Kinetics
  • Naphthalenes / chemistry*
  • Oxidation-Reduction
  • Solutions / chemistry*
  • Water / chemistry
  • o-Phthalaldehyde / chemistry*

Substances

  • Amino Acids
  • Buffers
  • Hydroxides
  • Naphthalenes
  • Solutions
  • Water
  • o-Phthalaldehyde
  • 2,3-naphthalenedicarboxaldehyde
  • hydroxide ion