Salcomine

Salcomine[1]
Other names N,N′-Bis(salicylidene)ethylenediaminocobalt(II)
Identifiers
CAS number	14167-18-1 Y
PubChem	11012797
Jmol-3D images	Image 1
SMILES C1=CC(=CNCCNC=C2C=CC=CC2=O)C(=O)C=C1.[Co]
Properties
Molecular formula	C16H14CoN2O2
Molar mass	325.23 g mol−1
Hazards
MSDS	Oxford MSDS
R-phrases	R36/37/38
S-phrases	S26 S36
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 salen^2-, 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

1. ^ N,N′-Bis(salicylidene)ethylenediaminocobalt(II) at Sigma-Aldrich
2. ^ ^{a b} 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. Ed. 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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0412 ; Coll. Vol. 6: 412