Salen ligand

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Salen ligand
Names
Other names
2,2′-Ethylenebis(nitrilomethylidene)diphenol, N,N′-Ethylenebis(salicylimine)
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.002.161 Edit this at Wikidata
EC Number
  • 202-376-3
UNII
  • InChI=1S/C16H16N2O2/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/b17-11+,18-12+
    Key: VEUMANXWQDHAJV-JYFOCSDGSA-N
  • C1=CC=C(C(=C1)/C=N/CC/N=C/C2=CC=CC=C2O)O
Properties
C16H16N2O2
Molar mass 268.32
Melting point 126 °C (259 °F; 399 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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This article is about Salen. For Complexes of salen and related ligands, see
Metal salen complexes
.

Salen refers to a

catalysts.[2]

Synthesis and properties

H2salen may be synthesized by the condensation of ethylenediamine and salicylaldehyde.[3]

Salcomine, a complex of salen with cobalt
Jacobsen's salen-Mn catalyst

Complexes of salen with metal cations may be made without isolating it from the reaction mixture.

chelate effect
.

H2L + Mn+ → ML(n−2)+ + 2 H+

where L stands for the ligand. The

dioxygen carrier by forming a labile, octahedral O2 complex.[6][7]

The name "salen ligands" is used for

asymmetric synthesis reactions, such as the Jacobsen epoxidation:[9][10]

Related ligands

Synthesis and complexation of Jäger's ligand.[11]

A class of tetradentate ligands with the generic name acacen are obtained by the condensation of derivatives of

oncogenesis.[12]

The salan and salalen ligands are similar in structure to salen ligands, but have one or two saturated nitrogen-aryl bonds (

alkyl halide. The “half-salen” ligands have only one salicylimine group. They are prepared from a salicylaldehyde and a monoamine.[15]

The name “salen” or “salen-type” may be used for other ligands that have similar environment around the chelating site, namely two acidic hydroxyls and two

2-quinoxalinol.[16]

See also

References

  1. PMID 15354222
    .
  2. S2CID 184486101
    .
  3. doi:10.1246/bcsj.13.252
    .
  4. ISBN 978-0-470-13234-0. {{cite book}}: |journal= ignored (help
    )
  5. ^
    PMID 15354222
    .
  6. doi:10.1021/ed054p443
    .
  7. doi:10.1016/S0010-8545(99)00099-5
    .
  8. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link
    )
  9. ^ Larrow, J. F.; Jacobsen, E. N. (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses; Collected Volumes, vol. 10, p. 96.
  10. S2CID 27416160
    .
  11. ^
    doi:10.1002/ejic.200990003
    .
  12. S2CID 73727460. {{cite book}}: |editor4-first= has generic name (help); |journal= ignored (help
    )
  13. doi:10.1021/om960505r
    .
  14. doi:10.1002/adsc.200700221
    .
  15. doi:10.1039/C4PY00734D
    .
  16. doi:10.1002/ejoc.200800928.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
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