Theoretical speciation of ethylenediamine-N-(o-hydroxyphenylacetic)-N'-(p-hydroxyphenylacetic) acid (o,p-EDDHA) in agronomic conditions

J Agric Food Chem. 2003 Aug 27;51(18):5391-9. doi: 10.1021/jf034304r.

Abstract

The presence of ethylenediamine-N-(o-hydroxyphenylacetic)-N'-(p-hydroxyphenylacetic) acid (o,p-EDDHA) as the second largest component in commercial EDDHA iron chelates has recently been demonstrated. Here is reported the speciation of o,p-EDDHA by the application of a novel methodology through the determination of the complexing capacity, protonation, and Ca(2+), Mg(2+), Cu(2+), and Fe(3+) stability constants. The pM values and species distribution in solution, hydroponic, and soil conditions were obtained. Due to the para position of one phenol group in o,p-EDDHA, the protonation constants and Ca and Mg stability constants have different values from those of o,o-EDDHA and p,p-EDDHA regioisomers. o,p-EDDHA/Fe(3+) stability constants are higher than those of EDTA/Fe(3+) but lower than those of o,o-EDDHA/Fe(3+). The sequence obtained for pFe is o,o-EDDHA/Fe(3+) >/= o,p-EDDHA/Fe(3+) > EDTA/Fe(3+). o,p-EDDHA/Fe(3+) can be used as an iron chelate in hydroponic conditions. Also, it can be used in soils with limited Cu availability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agriculture*
  • Calcium / chemistry
  • Copper / chemistry
  • Drug Stability
  • Ethylenediamines / analysis
  • Ethylenediamines / chemistry*
  • Ferric Compounds / chemistry
  • Hydrogen-Ion Concentration
  • Iron Chelating Agents / chemistry
  • Magnesium / chemistry
  • Magnetic Resonance Spectroscopy
  • Spectrophotometry

Substances

  • Ethylenediamines
  • Ferric Compounds
  • Iron Chelating Agents
  • ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid)
  • Copper
  • Magnesium
  • Calcium