Iminodiacetic acid is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula HN(CH₂CO₂H)₂, often abbreviated to IDA. A white solid, the compound is a

dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show ...

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...

(the nitrogen atom forms a secondary amino group, not an

imino In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

group as the name suggests). The iminodiacetate dianion is a tridentate

ligand In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electr ...

, forming metal complexes by forming two, fused, five membered

chelate Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an

ion-exchange resin An ion-exchange resin or ion-exchange polymer is a resin or polymer that acts as a medium for ion exchange. It is an insoluble matrix (or support structure) normally in the form of small (0.25–1.43 mm radius) microbeads, usually white or ye ...

, such as

chelex 100 Chelex 100 is a chelating material from Bio-Rad used to purify other compounds via ion exchange. It is noteworthy for its ability to bind transition metal ions. It is a styrene-divinylbenzene co-polymer containing iminodiacetic acid groups. A conc ...

. Complexes of IDA and EDTA were introduced in the early 1950's by Schwarzenbach. Ferric(ida)2 anion

IDA forms stronger complexes than the bidentate ligand

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinogeni ...

and weaker complexes than the tetradentate ligand

nitrilotriacetic acid Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH2CO2H)3. It is a colourless solid that is used as a chelating agent, which forms coordination compounds with metal ions (chelates) such as Ca2+, Co2+, Cu2+, and Fe3 ...

. It can also act as a bidentate ligand through its two carboxylate groups. Several technetium-99''m'' complexes are used in

cholescintigraphy Cholescintigraphy or hepatobiliary scintigraphy is scintigraphy of the hepatobiliary tract, including the gallbladder and bile ducts. The image produced by this type of medical imaging, called a cholescintigram, is also known by other names depen ...

scans (also known as ''hepatobiliary iminodiacetic acid scans'') to evaluate the health and function of the

gallbladder In vertebrates, the gallbladder, also known as the cholecyst, is a small hollow organ where bile is stored and concentrated before it is released into the small intestine. In humans, the pear-shaped gallbladder lies beneath the liver, although ...

. Iminodiacetic acid is an important intermediate in one of the two main industrial processes used to manufacture the herbicide

glyphosate Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum Herbicide, systemic herbicide and Crop desiccation, crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plan ...

. It is used in

capillary electrophoresis Capillary electrophoresis (CE) is a family of electrokinetic separation methods performed in submillimeter diameter capillaries and in micro- and nanofluidic channels. Very often, CE refers to capillary zone electrophoresis (CZE), but other electr ...

for modulating peptide mobility. It is also used as a precursor for the manufacture of the

indicator Indicator may refer to: Biology * Environmental indicator of environmental health (pressures, conditions and responses) * Ecological indicator of ecosystem health (ecological processes) * Health indicator, which is used to describe the health o ...

xylenol orange Xylenol orange is an organic reagent, most commonly used as a tetrasodium salt as an indicator for metal titrations. When used for metal titrations, it will appear red in the titrand and become yellow once it reaches its endpoint. Historically, ...

References

{{Reflist Dicarboxylic acids Chelating agents Amines

See also

References