Iminodiacetic acid: Difference between revisions - Wikipedia

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{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 396495109408567508

| ImageFile = Iminodiacetic acid.pngsvg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 160

| IUPACName = 2-(carboxymethylamino)acetic acid

| ImageName = Skeletal formula of iminodiacetic acid

| OtherNames = Diglycolamidic acid

| PIN = 2,2′-Azanediyldiacetic acid

| Section1={{Chembox Identifiers▼

| OtherNames = 2-(Carboxymethylamino)acetic acid<br />Diglycolamidic acid

| InChI = 1/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)

▲| Section1={{Chembox Identifiers

| InChIKey = NBZBKCUXIYYUSX-UHFFFAOYAF

| CASNo = 142-73-4▼

| CASNo_Ref = {{cascite|correct|CAS}}▼

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XQM2L81M8Z

| PubChem = 8897

| ChemSpiderID = 8557▼

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}▼

| EC-numberEINECS = 205-555-4▼

| KEGG = C19911

| KEGG_Ref = {{keggcite|changed|kegg}}

| MeSHName = imnodiacetic+acid

| ChEBI = 24786

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 461164

| StdInChI_RefChEMBL_Ref = {{stdinchiciteebicite|correct|chemspiderEBI}}

| RTECS = AI2975000

| Beilstein = 878499

| SMILES = OOC(=C(O)CNCC(=O)=O▼

| StdInChI = 1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)

| StdInChIKey_RefStdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NBZBKCUXIYYUSX-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

▲| CASNo = 142-73-4

}}▼

▲| CASNo_Ref = {{cascite|correct|CAS}}

| Section2={{Chembox Properties▼

▲| EC-number = 205-555-4

| C=4 | H=7 | N=1 PubChem| O=4 8897

| Appearance = Colourless crystals

▲| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| Density = 1.436 g/cm mL³⁻¹ ▼

▲| ChemSpiderID = 8557

| LogP = 1.84

▲| SMILES = O=C(O)CNCC(=O)O

| pKa = 1.873

| pKb = 12.124

}}▼

| Section3 = {{Chembox HazardsThermochemistry▼

| DeltaHf = −933.9–−931.3 kJ mol⁻¹

| DeltaHc = −1.6430–−1.6406 MJ mol⁻¹

}}

|Section4={{Chembox Hazards

| GHSPictograms = {{gHS exclamation mark}}

| GHSSignalWord = '''WARNING'''

| HPhrases = {{h-phrases|315|319|335}}

| PPhrases = {{p-phrases|261|305+351+338}}

| FlashPtC = 178

}}

|Section5={{Chembox Related

| OtherFunction_label = alkanoic acids

| OtherFunction = {{unbulleted list|[[Acetylcysteine]]|[[Glycylglycine]]|[[Nitrilotriacetic acid]]|[[n-Oxalylglycine|''N''-Oxalylglycine]]|[[Tiopronin]]|[[Bucillamine]]|[[Oxalyldiaminopropionic acid]]}}

| OtherCompounds = [[n-Acetylglycinamide|''N''-Acetylglycinamide]]

}}

▲| Section2={{Chembox Properties

| C = 4 | H = 7 | N = 1 | O = 4

| Appearance =

▲| Density = 1.436 g/cm³

| MeltingPt = 247.5 °C

| BoilingPt =

| Solubility =

▲ }}

▲| Section3 = {{Chembox Hazards

| EUIndex = not listed

| FlashPt = 178 °C

| Autoignition =

▲ }}

}}

'''Iminodiacetic acid''', is the [[organic compound]] with the formula HN(CH₂CO₂H)₂, often abbreviated to '''IDA'''. A white solid, the compound is ana [[dicarboxylic acid]] [[amine]]. The(the iminodiacetatenitrogen anionatom canforms acta secondary amino group, not an [[imino]] group as the name suggests). The iminodiacetate dianion is a [[tridentate]] [[ligand]], to form aforming metal complexcomplexes withby forming two, fused, five membered [[chelate]] rings.<ref>{{cite journal |lastname=Schwarzenbach |first=G |year=1952 |title=Der Chelateffekt |journal=Helv. Chim. Acta|volume=35|pages=2344–2359|doi=10.1002AnnieP/hlca.19520350721}}</ref> 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]]. Complexes of IDA and EDTA were introduced in the early 1950s by Schwarzenbach.<ref>{{cite journal |last=Schwarzenbach |first=G |year=1952 |title=Der Chelateffekt |journal=Helv. Chim. Acta|volume=35|pages=2344–2359|doi=10.1002/hlca.19520350721 |issue=7}}</ref>

[[File:Ferric(ida)2 anion.svg|thumb|left|Structure of an iron(III) bis ida complex.<ref name=AnnieP>{{cite journal |doi=10.1016/S0010-8545(02)00110-8|title=Synthesis, structures and properties of hydrolytic Al(III) aggregates and Fe(III) analogues formed with iminodiacetate-based chelating ligands|year=2002|last1=Schmitt|first1=Wolfgang|last2=Jordan|first2=Peter A.|last3=Henderson|first3=Richard K.|last4=Moore|first4=Geoffrey R.|last5=Anson|first5=Christopher E.|last6=Powell|first6=Annie K.|journal=Coordination Chemistry Reviews|volume=228|issue=2|pages=115–126}}</ref>]]

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

IDA forms stronger complexes than the bidentate ligand [[glycine]] and weaker complexes than the tetradentate ligand [[nitrilotriacetic acid]]. It can also act as a bidentate ligand through its two carboxylate groups. Several [[technetium-99m|technetium-99''m'']] complexes are used in [[cholescintigraphy]] scans (also known as ''hepatobiliary iminodiacetic acid scans'') to evaluate the health and function of the [[gallbladder]].<ref>{{cite web|url = http://www.mayoclinic.com/health/hida-scan/AN00424|title = HIDA scan (cholescintigraphy): Why is it performed?|access-date = 11 December 2007|last = Michael|first = Picco|publisher = [[Mayo Clinic]]}}</ref><ref>{{cite book|first1 = Gerbail T.|last1 = Krishnamurthy|first2 = Shakuntala|last2 = Krishnamurthy|title = Nuclear Hepatology: A Textbook of Hepatobiliary Diseases|chapter = Imaging Agents|pages = 54–57|url = https://books.google.com/books?id=IXaPDIiGeg4C&q=iminodiacetic+acid|access-date = 19 December 2015|date = 2009|publisher = [[Springer Science+Business Media|Springer]]|isbn = 978-3-642-00647-0}}</ref>

[[Image:mida.svg|thumb|left|A metal complex with the iminodiacetate anion]]{{clear-left}}

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 [[Electrical mobility|peptide mobility]]. It is also used as a precursor for the manufacture of the [[PH indicator|indicator]] [[xylenol orange]].

==See also==

* [[HIDA scan]]

==Related compounds==

* [[N-Methylimidodiacetic acid]] (MIDA)

* [[N-(2-Carboxyethyl)iminodiacetic acid]]

* [[Nitrilotriacetic acid]] (NTA)

* N-hydroxyiminodiacetic acid (HIDA), {{chem2|HON(CH2CO2H)2}} ([[registry number]] = 87339-38-6)<ref>{{cite journal |doi=10.1002/ejoc.200601053 |title=Stabilizing Factors for Vanadium(IV) in Amavadin |date=2007 |last1=Hubregtse |first1=Ton |last2=Hanefeld |first2=Ulf |last3=Arends |first3=Isabel W. C. E. |journal=European Journal of Organic Chemistry |volume=2007 |issue=15 |pages=2413–2422 }}</ref> See [[HIDA scan]].

==References==

{{reflistReflist}}

[[Category:Equilibrium chemistry]]

[[Category:Dicarboxylic acids]]

[[Category:Chelating agents]]

[[Category:Amines]]

[[de:Iminodiessigsäure]]