# Salcomine

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> Markdown URL: https://mediated.wiki/source/Salcomine.md
> Source: https://en.wikipedia.org/wiki/Salcomine
> Source revision: 1196529195
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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447538257
| Reference=<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/274712 N,N{{prime}}-Bis(salicylidene)ethylenediaminocobalt(II)] at [Sigma-Aldrich](/source/Sigma-Aldrich)</ref>
| ImageFile1= Salcomine.png
| ImageSize1= 150px
| ImageFile2= Salcomine-3D-balls-by-AHRLS-2012.png
| ImageSize2= 200px
| IUPACName=
| OtherNames={{plain list|
*''N,N{{prime}}''-Bis(salicylidene)ethylenediaminocobalt(II)
*Co(salen)}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=14167-18-1 
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 24701
|  PubChem = 26517
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = N2O9115YTK
|  SMILES = c1cc(c(cc1)[O-])/C=N/CC/N=C/c2c(cccc2)[O-].[Co+2]
|  SMILES_Comment = ionic form
|  SMILES1 = C1C[N+]2=Cc0ccccc0O[Co-2]23Oc0ccccc0C=[N+]13
|  SMILES1_Comment = coordination form
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C16H16N2O2.Co/c19-15-7-3-1-5-13(15)11-17-9-10-18-12-14-6-2-4-8-16(14)20;/h1-8,11-12,19-20H,9-10H2;/q;+2/p-2/b17-11+,18-12+;
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NPAQSKHBTMUERN-OYJDLGDISA-L
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|Section2={{Chembox Properties
| C=16 | H=14 | Co=1 | N=2 | O=2
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
 }}
|Section3={{Chembox Hazards
| ExternalSDS = [http://msds.chem.ox.ac.uk/BI/N,N%27-bis(salicylidene)ethylenediamino_cobalt(II).html Oxford MSDS]
| FlashPt=
| AutoignitionPt =
| GHS_ref=<ref>{{cite web |title=SAFETY DATA SHEET |url=https://www.sigmaaldrich.com/AU/en/sds/aldrich/274712 |access-date=15 December 2021 |date=27 November 2021}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|P261|P264|P271|P280|P304 + P340 + P312|P332 + P313|P337 + P313 |P362 + P364|P403 + P233|P501}}
 }}
}}

'''Salcomine''' is a [coordination complex](/source/coordination_complex) derived from the [salen ligand](/source/salen_ligand) and cobalt. The complex, which is planar, and a variety of its derivatives are [carriers for O<sub>2</sub>](/source/dioxygen_complex) as well as oxidation catalysts.<ref name=Yamada>Shoichiro Yamada "Advancement in stereochemical aspects of Schiff base metal complexes" Coordination Chemistry Reviews 1999, volume 190–192, 537–555.</ref>

==Preparation and structure==
Salcomine is commercially available. It may be synthesized from [cobalt(II) acetate](/source/cobalt(II)_acetate) and [salenH<sub>2</sub>](/source/salen_ligand).<ref>{{cite journal | doi = 10.1021/ed054p443 | journal = [J. Chem. Educ.](/source/J._Chem._Educ.) | title = Oxygen Uptake by a Cobalt(II) Complex | author = Appleton, T. G. | year = 1977 | volume = 54 | issue = 7 | page = 443}}</ref>

Salcomine crystallizes as a dimer. In this form, the cobalt centers achieve five-coordination via a bridging phenolate ligands.<ref>{{cite journal|author1=Bruckner, S. |author2=Calligaris, M. |author3=Nardin, G. |author4=Randaccio, L. |title=The Crystal Structure of the Form of N,N-Ethylenebis(salicylaldehydeiminato)cobalt(II) Inactive Towards Oxygenation|journal=Acta Crystallographica Section B|year=1969|volume=25|issue=8|pages=1671–1674|doi=10.1107/S0567740869004523|doi-access=}}</ref> A monomeric form crystallizes with chloroform in the lattice.  It features planar Co centers.<ref>{{cite journal|author1=Schaefer, W. P. |author2=Marsh, R. E. |title=Oxygen-Carrying Cobalt Compounds. I. Bis(salicylaldehyde)ethylenediiminecobalt(II) Monochloroformate|journal=Acta Crystallographica Section B |year=1969|volume=25|issue=9|pages=1675–1682|doi=10.1107/S0567740869004547}}</ref> Salcomine is both a Lewis acid and a reductant. Several solvated derivatives bind O<sub>2</sub> to give derivatives of the type (μ-O<sub>2</sub>)[Co(salen)py]<sub>2</sub> and [Co(salen)py(O<sub>2</sub>)].<ref name=Yamada/>

==Applications==
[[File:DOESCF10.svg|thumb|left|Structure of [Co(salen)([dmf](/source/Dimethylformamide))]<sub>2</sub>O<sub>2</sub><ref>{{cite journal|journal=J. Chem. Soc. A |author=M. Calligaris |author2=G. Nardin |author3=L. Randaccio |author4=A. Ripamonti |year=1970|page=1069|title=Structural Aspects of the Synthetic Oxygen-Carrier NN{{prime}}-Ethylenebis(Salicylideneiminato)cobalt(II): Structure of the Addition Compound with Oxygen Containing Dimethylformamide|doi=10.1039/j19700001069}}</ref>]]
The 1938 report that this compound reversibly bound O<sub>2</sub><ref>{{cite journal | author = Tokuichi Tsumaki | title = Nebenvalenzringverbindungen. IV. Über einige innerkomplexe Kobaltsalze der Oxyaldimine | journal = [Bulletin of the Chemical Society of Japan](/source/Bulletin_of_the_Chemical_Society_of_Japan) | year = 1938 | volume = 13 | issue = 2 | pages = 252–260 | doi = 10.1246/bcsj.13.252| doi-access = free }}</ref> led to intensive research on this and related complexes for the storage or transport of oxygen. Solvated derivatives of salcomine, e.g. the chloroformate or the DMF adduct, bind 0.5 equivalent of O<sub>2</sub>:
:2 Co(salen) + O<sub>2</sub> → [Co(salen)]<sub>2</sub>O<sub>2</sub>

Salcomine catalyzes the oxidation of 2,6-disubstituted phenols by dioxygen.<ref>{{OrgSynth | collvol = 6 | collvolpages = 412 | year = 1988 | prep = cv6p0412 | title = <nowiki>Oxidation with Bis(Salicylidene)ethylenediiminocobalt(II) (Salcomine): 2,6-Di-''tert''-butyl-''p''-benzoquinone</nowiki> |author=C. R. H. I. De Jonge |author2=H. J. Hageman |author3=G. Hoentjen |author4=W. J. Mijs
}}</ref>

==References==
<references/>

Category:Metal salen complexes
Category:Cobalt compounds

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Adapted from the Wikipedia article [Salcomine](https://en.wikipedia.org/wiki/Salcomine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Salcomine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.