Salcomine

Salcomine^[1]
Names
	Other names N,N′-Bis(salicylidene)ethylenediaminocobalt(II); Co(salen);
Identifiers
CAS Number	14167-18-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	24701 ;
ECHA InfoCard	100.034.541
PubChem CID	26517;
CompTox Dashboard (EPA)	DTXSID1065718 ;
	InChI InChI=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+; Key: NPAQSKHBTMUERN-OYJDLGDISA-L ;
	SMILES c1cc(c(cc1)[O-])/C=N/CC/N=C/c2c(cccc2)[O-].[Co+2];
Properties
Chemical formula	C16H14CoN2O2
Molar mass	325.233 g·mol−1
Hazards
Safety data sheet (SDS)	Oxford MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Salcomine is a coordination complex derived from the salen ligand and cobalt. The complex, which is planar, and a variety of its derivatives are carriers for O₂ as well as oxidation catalysts.^[2]

Preparation and structure

The compound features square planar Co(II). It forms a variety of five-coordinate adducts, as is typical for complexes of d⁷ metals. In addition to oxygen and nitrogen donor sites provided by the salen²⁻, the metal typically is bound to pyridine (py) to give the complex Co(salen)(py). Such complexes bind O₂ to give derivatives of the type (μ-O₂)[Co(salen)py]₂ and [Co(salen)py(O₂)].^[2]

Salcomine is commercially available. It may be easily synthesized from cobalt(II) acetate and salenH₂:^[3]

Applications

The 1938 report that this compound reversibly bound O₂ led to intensive research on salen and related ligands for the storage or transport of oxygen.^[4] Salcomine catalyzes the oxidation of 2,6-disubstituted phenols by dioxygen.^[5]

References

^ N,N′-Bis(salicylidene)ethylenediaminocobalt(II) at Sigma-Aldrich
^ ^a ^b Shoichiro Yamada “Advancement in stereochemical aspects of Schiff base metal complexes” Coordination Chemistry Reviews 1999, volume 190–192, 537–555.
^ Appleton, T. G. (1977). "Oxygen Uptake by a Cobalt(II) Complex". J. Chem. Educ. 54 (7): 443. doi:10.1021/ed054p443.
^ Tokuichi Tsumaki (1938). "Nebenvalenzringverbindungen. IV. Über einige innerkomplexe Kobaltsalze der Oxyaldimine". Bulletin of the Chemical Society of Japan. 13 (2): 252–260. doi:10.1246/bcsj.13.252.
^ C. R. H. I. De Jonge, H. J. Hageman, G. Hoentjen, and W. J. Mijs (1988). "Oxidation with Bis(Salicylidene)ethylenediiminocobalt(II) (Salcomine): 2,6-Di-''tert''-butyl-''p''-benzoquinone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 412.

[1] N,N′-Bis(salicylidene)ethylenediaminocobalt(II) at Sigma-Aldrich

[Yamada-2] Shoichiro Yamada “Advancement in stereochemical aspects of Schiff base metal complexes” Coordination Chemistry Reviews 1999, volume 190–192, 537–555.

[3] Appleton, T. G. (1977). "Oxygen Uptake by a Cobalt(II) Complex". J. Chem. Educ. 54 (7): 443. doi:10.1021/ed054p443.

[4] Tokuichi Tsumaki (1938). "Nebenvalenzringverbindungen. IV. Über einige innerkomplexe Kobaltsalze der Oxyaldimine". Bulletin of the Chemical Society of Japan. 13 (2): 252–260. doi:10.1246/bcsj.13.252.

[5] C. R. H. I. De Jonge, H. J. Hageman, G. Hoentjen, and W. J. Mijs (1988). "Oxidation with Bis(Salicylidene)ethylenediiminocobalt(II) (Salcomine): 2,6-Di-''tert''-butyl-''p''-benzoquinone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 412.

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