dicobalt edetate

{{chembox

| Verifiedfields = changed

| verifiedrevid = 399896543

| ImageFile=Dicobalt edetate.png

| ImageSize=230

| ImageAlt=Skeletal formula of dicobalt edetate

| ImageFile1=Dicobalt edetate 3D ball.png

| ImageSize1=250

| ImageAlt1=Ball-and-stick model of the dicobalt edetate molecule

| IUPACName=

| OtherNames=Kelocyanor

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = UKC6GH80QR

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

| ChemSpiderID = 64951

| InChI = 1/C10H16N2O8.2Co/c13-7(14)3-11(4-8(15)16)1-2-12(5-9(17)18)6-10(19)20;;/h1-6H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20);;/q;2*+2/p-4

| InChIKey = TWAWHTJKASJPEK-XBHQNQODAQ

| SMILES1 = [Co+2].[Co+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H16N2O8.2Co/c13-7(14)3-11(4-8(15)16)1-2-12(5-9(17)18)6-10(19)20;;/h1-6H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20);;/q;2*+2/p-4

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

| StdInChIKey = TWAWHTJKASJPEK-UHFFFAOYSA-J

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=36499-65-7

| PubChem=71942

| SMILES=C(CN(CC(=O)[O-])CC(=O)[O-])N(CC(=O)[O-])CC(=O)[O-].[Co+2].[Co+2]

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|Section2={{Chembox Properties

| Formula=C10H12Co2N2O8.6H2O

| MolarMass=406.08 g/mol
514.18 g/mol (hexahydrate)

| Appearance=

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|Section3={{Chembox Hazards

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Dicobalt edetate is the coordination compound with the approximate formula Co2(EDTA)(H2O)6. It is a derivative of the (non-natural) amino acid ethylenediaminetetraacetate.

Solutions of this solid have been used in Europe as an antidote to cyanide poisoning, with the trade name Kelocyanor.{{cite journal |author=Pickering WG |title=Cyanide toxicity and the hazards of dicobalt edetate |journal=Br Med J (Clin Res Ed) |volume=291 |issue=6509 |pages=1644 |date=December 1985 |pmid=2866807 |pmc=1418389 |doi= 10.1136/bmj.291.6509.1644-a}} However, dicobalt edetate is itself toxic, particularly if there is not enough cyanide in the blood to react with it, so it is only suitable for serious cases of poisoning. In the past, workplaces in the UK that handle cyanide were recommended to keep a 'Kelocyanor kit', to be taken to the hospital along with the patient, but this practice has been discontinued since it may mislead doctors into using the antidote unnecessarily.{{cite web |url=http://www.hse.gov.uk/pubns/misc076.htm |title=Cyanide poisoning – New recommendations on first aid treatment |publisher=Health and Safety Executive |url-status=live |archive-url=https://web.archive.org/web/20091020204249/http://www.hse.gov.uk/pubns/misc076.htm |archive-date=20 October 2009 }}

Structure

The compound is polymeric in the crystalline form. Half of the Co2+ ions are bound to the EDTA2− and the other Co2+ ions are bound to four water ligands as well as carboxylate ligands on the [Co(EDTA)]2− entity.{{cite journal | last1 = E. F. K. Mccandlish | first1 = T. K. Michael | last2 = Rose | first2 = N. J. | year = 1978 | title = Comparison of the Structures and Aqueous Solutions of [(O-Phenylenediaminetetraacetato(2-)]Cobalt(II) and [Ethylenediaminetetraacetato(2-)]Cobalt(II) | journal = Inorg. Chem. | volume = 17 | pages = 1383–94 | doi = 10.1021/ic50184a001 | last3 = Neal | first3 = J. A. | last4 = Lingafelter | first4 = E. C. | last5 = Rose | first5 = N. J. | issue = 6}} In aqueous solution, depolymerization occurs to give [Co(EDTA)]2− and [Co(H2O)6]2+ ions, each of which is kinetically labile and has a high affinity for cyanide.

Related compounds

Oxidation of [Co(II)(EDTA)]2− gives [Co(III)(EDTA)], which is so kinetically inert that it can be resolved optically.{{cite book | last1 = Dwyer | first1 = F. P. | last2 = Garvan | first2 = F. L. | title = Inorganic Syntheses | chapter = Resolution of the Ethylenediaminetetraacetatocobaltate(III) Ion | journal = Inorg. Synth.| volume = VI | pages = 192–4 | date = 1960 | doi = 10.1002/9780470132371.ch61 | isbn = 978-0-470-13237-1}}

References