Salcomine
| Salcomine[1] | |
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Other names
N,N′-Bis(salicylidene)ethylenediaminocobalt(II) |
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| Identifiers | |
| CAS number | 14167-18-1  |
| PubChem | 11012797 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C16H14CoN2O2 |
| Molar mass | 325.23 g mol−1 |
| Hazards | |
| MSDS | Oxford MSDS |
| R-phrases | R36/37/38 |
| S-phrases | S26 S36 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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]
[edit] 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]
[edit] 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]
[edit] 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. Ed. 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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0412; Coll. Vol. 6: 412
