Salcomine

Salcomine^[1]
Names
	Other names N,N′-Bis(salicylidene)ethylenediaminocobalt(II); Co(salen);
Identifiers
CAS Number	14167-18-1 ;
3D model (JSmol)	ionic form: Interactive image; coordination form: Interactive image;
ChemSpider	24701 ;
ECHA InfoCard	100.034.541
PubChem CID	26517;
UNII	N2O9115YTK ;
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 ionic form: c1cc(c(cc1)[O-])/C=N/CC/N=C/c2c(cccc2)[O-].[Co+2]; coordination form: C1C[N+]2=Cc0ccccc0O[Co-2]23Oc0ccccc0C=[N+]13;
Properties
Chemical formula	C16H14CoN2O2
Molar mass	325.233 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P304+P340+P312, P332+P313, P337+P313, P362+P364, P403+P233, P501
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.^[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,N′-Bis(salicylidene)ethylenediaminocobalt(II) at Sigma-Aldrich
^ "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.
^ Appleton, T. G. (1977). "Oxygen Uptake by a Cobalt(II) Complex". J. Chem. Educ. 54 (7): 443. doi:10.1021/ed054p443.
^ 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.
^ 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.
^ M. Calligaris; G. Nardin; L. Randaccio; A. Ripamonti (1970). "Structural Aspects of the Synthetic Oxygen-Carrier NN′-Ethylenebis(Salicylideneiminato)cobalt(II): Structure of the Addition Compound with Oxygen Containing Dimethylformamide". J. Chem. Soc. A: 1069. doi:10.1039/j19700001069.
^ 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; W. J. Mijs (1988). "Oxidation with Bis(Salicylidene)ethylenediiminocobalt(II) (Salcomine): 2,6-Di-''tert''-butyl-''p''-benzoquinone". Organic Syntheses; Collected Volumes, vol. 6, p. 412.

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

[2] "SAFETY DATA SHEET". 27 November 2021. Retrieved 15 December 2021.

[Yamada-3] Shoichiro Yamada "Advancement in stereochemical aspects of Schiff base metal complexes" Coordination Chemistry Reviews 1999, volume 190–192, 537–555.

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

[5] 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.

[6] 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.

[7] M. Calligaris; G. Nardin; L. Randaccio; A. Ripamonti (1970). "Structural Aspects of the Synthetic Oxygen-Carrier NN′-Ethylenebis(Salicylideneiminato)cobalt(II): Structure of the Addition Compound with Oxygen Containing Dimethylformamide". J. Chem. Soc. A: 1069. doi:10.1039/j19700001069.

[8] 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.

[9] 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; Collected Volumes, vol. 6, p. 412.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]