Salcomine
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C16H14CoN2O2 | |
| Molar mass | 325.233 g·mol−1 |
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| 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).
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Template:Chembox Footer/trackingTemplate:Short description
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.[3]
Preparation and structure
Salcomine is commercially available. It may be synthesized from cobalt(II) acetate and salenH2.[4]
Salcomine crystallizes as a dimer. In this form, the cobalt centers achieve five-coordination via a bridging phenolate ligands.[5] A monomeric form crystallizes with chloroform in the lattice. It features planar Co centers.[6] Salcomine is both a Lewis acid and a reductant. Several solvated derivatives bind O2 to give derivatives of the type (μ-O2)[Co(salen)py]2 and [Co(salen)py(O2)].[3]
Applications
The 1938 report that this compound reversibly bound O2[8] 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 O2:
- 2 Co(salen) + O2 → [Co(salen)]2O2
Salcomine catalyzes the oxidation of 2,6-disubstituted phenols by dioxygen.[9]
References
- ^ N,NTemplate:Prime-Bis(salicylidene)ethylenediaminocobalt(II) at Sigma-Aldrich
- ^ Page Module:Citation/CS1/styles.css has no content."SAFETY DATA SHEET". 27 November 2021. Retrieved 15 December 2021.
- ^ a b Shoichiro Yamada "Advancement in stereochemical aspects of Schiff base metal complexes" Coordination Chemistry Reviews 1999, volume 190–192, 537–555.
- ^ Page Module:Citation/CS1/styles.css has no content.Appleton, T. G. (1977). "Oxygen Uptake by a Cobalt(II) Complex". J. Chem. Educ. 54 (7): 443. doi:10.1021/ed054p443.
- ^ Page Module:Citation/CS1/styles.css has no content.Bruckner, S.; Calligaris, M.; Nardin, G.; Randaccio, L. (1969). "The Crystal Structure of the Form of N,N-Ethylenebis(salicylaldehydeiminato)cobalt(II) Inactive Towards Oxygenation". Acta Crystallographica Section B. 25 (8): 1671–1674. doi:10.1107/S0567740869004523.
- ^ Page Module:Citation/CS1/styles.css has no content.Schaefer, W. P.; Marsh, R. E. (1969). "Oxygen-Carrying Cobalt Compounds. I. Bis(salicylaldehyde)ethylenediiminecobalt(II) Monochloroformate". Acta Crystallographica Section B. 25 (9): 1675–1682. doi:10.1107/S0567740869004547.
- ^ Page Module:Citation/CS1/styles.css has no content.M. Calligaris; G. Nardin; L. Randaccio; A. Ripamonti (1970). "Structural Aspects of the Synthetic Oxygen-Carrier NNTemplate:Prime-Ethylenebis(Salicylideneiminato)cobalt(II): Structure of the Addition Compound with Oxygen Containing Dimethylformamide". J. Chem. Soc. A: 1069. doi:10.1039/j19700001069.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.C. R. H. I. De Jonge; H. J. Hageman; G. Hoentjen; W. J. Mijs (1988). "Oxidation with Bis(Salicylidene)ethylenediiminocobalt(II) (Salcomine): 2,6-Di-''tert''-butyl-''p''-benzoquinone". Organic Syntheses; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 6, p. 412.
