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

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

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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
Volume35
Issue number12
DOIs
Publication statusPublished - 1987

Fingerprint

hydrazine
Metals
Acids
Methanol
Hydrazines
Dimethylhydrazines
Chelation
Absorption spectroscopy
Metal ions
Nitrogen
Salts
Oxygen
Ligands
Spectrum Analysis
Atoms
Ions
Chemical analysis

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

N-Pyridoxylidenehydrazine-N’, N’-diacetic Acid. III.1) Formation of Metal Chelates in Solution. / Matsushima, Yoshikazu; Itoh, Yoshiko; Tamano, Yuko; Sugata, Setsuro; Fujie, Tadao; Karube, Yoshiharu; Kono, Akira.

In: Chemical and Pharmaceutical Bulletin, Vol. 35, No. 12, 1987, p. 4695-4699.

Research output: Contribution to journalArticle

Matsushima, Yoshikazu ; Itoh, Yoshiko ; Tamano, Yuko ; Sugata, Setsuro ; Fujie, Tadao ; Karube, Yoshiharu ; Kono, Akira. / N-Pyridoxylidenehydrazine-N’, N’-diacetic Acid. III.1) Formation of Metal Chelates in Solution. In: Chemical and Pharmaceutical Bulletin. 1987 ; Vol. 35, No. 12. pp. 4695-4699.
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AB - 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.

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