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Comparison of Solution Chemistries of Orthophthalaldehyde and 2,3-naphthalenedicarboxaldehyde

Comparison of Solution Chemistries of Orthophthalaldehyde and 2,3-naphthalenedicarboxaldehyde

N Salem, P Zuman

Anal Chem. 2006 Nov 15;78(22):7802-8.

PMID: 17105174

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7149497	2,3-Naphthalenedicarboxaldehyde		7149-49-7	Price

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