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Iminodiacetic acid

Iminodiacetic acid

Diglycolamidic acid

Iminodiacetic acid is the organic compound with the formula HN(CH2CO2H)2, often abbreviated to IDA. A white solid, the compound is a dicarboxylic acid amine (the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). IDA is a popular chelating ligand, first introduced in the early 1950s by Schwarzenbach.

Ligand

The iminodiacetate dianion is typically a tridentate ligand, forming metal complexes by forming two, fused, five membered chelate rings. IDA thus forms stronger complexes than the bidentate ligand glycine and weaker complexes than the tetradentate ligand nitrilotriacetic acid.

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IDA can also act as a bidentate ligand through its two carboxylate groups. Several technetium-99m complexes with bidentate IDA derivatives are used in cholescintigraphy scans (the so-called "hepatobiliary iminodiacetic acid scans") to evaluate the health and function of the gallbladder. Common IDA derivatives include lidofenin, mebrofenin, and disofenin that replace the secondary amine proton with an amide and aromatic substituent.

The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100.

Other applications

Iminodiacetic acid is an important intermediate in one of the two main industrial processes used to manufacture the herbicide glyphosate. It is used in capillary electrophoresis for modulating peptide mobility. It is also used as a precursor for the manufacture of the indicator xylenol orange.

Synthesis

A most efficient iminodiacetic synthesis dehydrogenates diethanolamine over a catalyst.

References

References

  1. Schwarzenbach, G. (1952). "Der Chelateffekt". Helv. Chim. Acta.
  2. (2002). "Synthesis, structures and properties of hydrolytic Al(III) aggregates and Fe(III) analogues formed with iminodiacetate-based chelating ligands". Coordination Chemistry Reviews.
  3. Michael, Picco. "HIDA scan (cholescintigraphy): Why is it performed?". [[Mayo Clinic]].
  4. (2009). "Nuclear Hepatology: A Textbook of Hepatobiliary Diseases". [[Springer Science+Business Media.
  5. Kowalsky, R.. "Technetium Radiopharmaceutical Chemistry Continuing Education for Nuclear Pharmacists and Nuclear Medicine Professionals By". [[Semantic Scholar]].
  6. "Process for preparing carboxylic acids by dehydrogenating alcohols".
  7. (2007). "Stabilizing Factors for Vanadium(IV) in Amavadin". European Journal of Organic Chemistry.
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dicarboxylic-acids chelating-agents secondary-amines
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