Salcomine

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Salcomine[1]
Names
Other names
  • N,N′-Bis(salicylidene)ethylenediaminocobalt(II)
  • Co(salen)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.541 Edit this at Wikidata
UNII
  • 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+; ☒N
    Key: NPAQSKHBTMUERN-OYJDLGDISA-L ☒N
  • 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
C16H14CoN2O2
Molar mass 325.233 g·mol−1
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
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).
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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

Structure of [Co(salen)(dmf)]2O2[7]

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

  1. ^ N,N′-Bis(salicylidene)ethylenediaminocobalt(II) at Sigma-Aldrich
  2. ^ "SAFETY DATA SHEET". 27 November 2021. Retrieved 15 December 2021.
  3. ^ a b 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.
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