N-Pyridoxylidenehydrazine-N’, N’-diacetic Acid. III.1) Formation of Metal Chelates in Solution

Yoshikazu Matsushima, Yoshiko Nagata, Yuko Tamano, Setsuro Sugata, Tadao Fujie, Yoshiharu Karube, Akira Kono

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Metal chelate formation of N-pyridoxylidenehydrazine-N1, N1-acid (1) and related hydrazines in solution was studied by means of absorption spectroscopy. Compound 1 and N-pyridoxylidene-N'-methylliydrazine (2) in methanol formed Cu(II) chelates of the same spectral character, which indicated the chelation of the phenolate oxygen and the hydrazine nitrogen atoms to Cu(II). The compositions of the chelates were 1:1 for 1 and 1:2 for 2, indicating that 1 acts as a tri- or tetradentate ligand. N-(3-Hydroxy-4-pyridylmethylene)hydrazine-N1,N'-diacetic acid formed a Cu(II) chelate similar to that of 1 but N-pyridoxylidene-N1,N1-dimethylhydrazine and N1,N1pyridoxylidene-N1.N1_diphenylhydrazine did not form chelates under similar conditions. Addition of an equimolar or excess amount of Co(II), Ni(II), Zn(II), Cd(II) or La(III) salt to 1 in methanol gave rise to absorption assignable to the chelate of 1, whereas 2 did not form metal chelates under the same conditions. It was concluded that the iminodiacetic acid moiety of 1 coordinated to the metal ions and enhanced the stability constant of the metal chelates.

Original languageEnglish
Pages (from-to)4695-4699
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Issue number12
Publication statusPublished - 1987


  • N-pyridoxyl-idenehydrazine-N1
  • N1-diacetic acid N-pyridoxylidene-N'
  • methylhydrazine metal chelate Cu(II) absorption spectrum
  • pyridoxal hydrazine hydrazone methanol iminodiacetic acid

ASJC Scopus subject areas

  • General Chemistry
  • Drug Discovery


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