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Updated: Jul 18, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Comparison of solution chemistries of orthophthalaldehyde and 2,3-naphthalenedicarboxaldehyde
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.
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