Iminodiacetic acid

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Iminodiacetic acid
Skeletal formula of iminodiacetic acid
Names
IUPAC name
2-(Carboxymethylamino)acetic acid
Other names
Diglycolamidic acid
Identifiers
878499
142-73-4 YesY
ChEBI CHEBI:24786 N
ChEMBL ChEMBL461164 YesY
ChemSpider 8557 YesY
EC number 205-555-4
Jmol-3D images Image
Image
KEGG C19911 N
MeSH imnodiacetic+acid
PubChem 8897
RTECS number AI2975000
Properties
C4H7NO4
Molar mass 133.10 g·mol−1
Appearance Colourless crystals
Density 1.436 g mL−1
log P 1.84
Acidity (pKa) 1.873
Basicity (pKb) 12.124
Thermochemistry
−933.9–−931.3 kJ mol−1
−1.6430–−1.6406 MJ mol−1
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H315, H319, H335
P261, P305+351+338
EU classification Irritant Xi
R-phrases R36/37/38
S-phrases S26, S36
Flash point 178 °C (352 °F; 451 K)
Related compounds
Related alkanoic acids
Related compounds
N-Acetylglycinamide
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Iminodiacetic acid, HN(CH2CO2H)2, often abbreviated to IDA, is a dicarboxylic acid amine (note that the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). The iminodiacetate anion can act as a tridentate ligand to form a metal complex with two, fused, five membered chelate rings.[1] 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.

IDA forms stronger complexes than the bidentate ligand glycine and weaker complexes than the tetradentate ligand nitrilotriacetic acid.

A metal complex with the iminodiacetate anion

By capillary electrophoresis IDA is typically used for modulating peptide mobility.

See also[edit]

References[edit]

  1. ^ Schwarzenbach, G (1952). "Der Chelateffekt". Helv. Chim. Acta 35 (7): 2344–2359. doi:10.1002/hlca.19520350721.