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{{chembox |
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| verifiedrevid = 418011133 |
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|ImageFile=Salen.jpg |
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| verifiedrevid = 450746497 |
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|ImageFile1=Salen structure.svg |
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| ImageFile=Salen structure.svg |
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|ImageSize=200px |
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| ImageSize=200px |
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|ImageFile2=Salen-3D-balls.png |
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| IUPACName= |
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|ImageSize1=200px |
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| OtherNames= 2,2′-Ethylenebis(nitrilomethylidene)diphenol, ''N'',''N''′-Ethylenebis(salicylimine) |
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|IUPACName= |
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|Section1={{Chembox Identifiers |
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|OtherNames= 2,2'-Ethylenebis(nitrilomethylidene)diphenol, N,N'-Ethylenebis(salicylimine) |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section1= {{Chembox Identifiers |
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| CASNo=94-93-9 |
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| CASNo=129409-01-4 |
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| CASNo_Ref = {{cascite}} |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 94-93-9 |
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| PubChem= |
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| CASNo1_Comment =(non-specific) |
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| EC_number = 202-376-3 |
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| PubChem=26518 |
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|Section2= {{Chembox Properties |
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| SMILES= C1=CC=C(C(=C1)/C=N/CC/N=C/C2=CC=CC=C2O)O |
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| Formula=C<sub>16</sub>H<sub>16</sub>N<sub>2</sub>O<sub>2</sub> |
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| 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+ |
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| MolarMass=268.31 |
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| InChIKey = VEUMANXWQDHAJV-JYFOCSDGSA-N |
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| Appearance=yellow solid |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Density= |
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| ChEMBL = 594100 |
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| MeltingPtC=125-129 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = M122L9EGR6 |
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| Solubility=organic solvents |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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}} |
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| ChemSpiderID = 10484366 |
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|Section3= {{Chembox Hazards |
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|Section2={{Chembox Properties |
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'''Salen''' is the abbreviation for a popular ] ] used in ] and ]. The name salen is a contraction for ] and ]. The ligand is a bright yellow micaceous solid that is soluble in polar organic solvents. |
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| Formula=C<sub>16</sub>H<sub>16</sub>N<sub>2</sub>O<sub>2</sub> |
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| MolarMass=268.32 |
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| MeltingPtC= 126 |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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{{about|Salen|Complexes of salen and related ligands|Metal salen complexes}} |
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'''Salen''' refers to a ] ] synthesized from ] ('''sal''') and ] ('''en'''). It may also refer to a class of compounds, which are structurally related to the classical salen ligand, primarily bis-]. Salen ligands are notable for coordinating a wide range of different metals, which they can often stabilise in various oxidation states.<ref>{{cite journal |last1=Cozzi |first1=Pier Giorgio |title=Metal–Salen Schiff base complexes in catalysis: practical aspects |journal=Chem. Soc. Rev. |date=2004 |volume=33 |issue=7 |pages=410–421 |doi=10.1039/B307853C|pmid=15354222 }}</ref> For this reason salen-type compounds are used as ]s. ] also find use as ].<ref>{{cite journal |last1=Shaw |first1=Subrata |last2=White |first2=James D. |title=Asymmetric Catalysis Using Chiral Salen–Metal Complexes: Recent Advances |journal=Chemical Reviews |volume=119 |issue=16 |pages=9381–9426 |date=11 June 2019 |doi=10.1021/acs.chemrev.9b00074|pmid=31184109 |s2cid=184486101 }}</ref> |
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==Synthesis and complexation== |
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==Nomenclature== |
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{{main|Metal salen complexes}} |
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The diphenol H<sub>2</sub>salen is the conjugate acid of the ligand that logically is salen<sup>2-</sup>. But the terminology is used loosely. As an ]ic ] ligand, salen<sup>2-</sup> resembles tetradentate ligands including those that are macrocyclic, such as ]ate, ], ], and some ]s. |
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H<sub>2</sub>salen may be synthesized by the ] of ethylenediamine and salicylaldehyde.<ref>{{cite journal | author = Tsumaki, T. | title = Nebenvalenzringverbindungen. IV. Über einige innerkomplexe Kobaltsalze der Oxyaldimine | journal = ] | year = 1938 | volume = 13 | issue = 2 | language = German | pages = 252–260 | doi = 10.1246/bcsj.13.252| doi-access = free }}</ref> |
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Complexes of salen with metal cations can often be made in situ, i.e., without isolating the H<sub>2</sub>salen.<ref>{{cite book | first1= Harvey |last1=Diehl|first2= Clifford C. |last2=Hach |title=Inorganic Syntheses |chapter=Bis( ''N,N'' '-Disalicylalethylenediamine)-μ - Aquodicobalt(II) | journal = ] | year = 1950 | volume = 3 | pages = 196–201 | doi = 10.1002/9780470132340.ch53 | isbn = 978-0-470-13234-0}}</ref><ref name = cozzi>{{cite journal | doi = 10.1039/B307853C | journal = Chem. Soc. Rev. | title = Metal-Salen Schiff base complexes in catalysis: Practical aspects | year = 2004 | author = Pier Giorgio Cozzi| volume = 33 | issue = 7 | pages = 410–421 | pmid=15354222}}</ref> |
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==Preparation== |
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:H<sub>2</sub>salen + M<sup>2+</sup> → M(salen) + 2 H<sup>+</sup> |
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SalenH<sub>2</sub> is commercially available. It was first prepared by Pfeiffer.<ref>{{cite journal | author = P. Pfeiffer, E. Breith, E. Lübbe, T. Tsumaki| title = "Tricyclische orthokondensierte Nebenvalenzringe | journal = ] | volume = 503 | pages = 84–130 | year = 1933 | doi = 10.1002/jlac.19335030106}}</ref> It is often generated in situ followed by the addition of the metal salt, but the ligand is also easily prepared as a pure organic compound by the ] of ] and ].<ref>{{cite journal | author = Harvey Diehl, Clifford C. Hach | journal = ] | year = 1950 | volume = 3 | pages = 196–201 | doi = 10.1002/9780470132340.ch53 | title = Bis(N,N' - Disalicylalethylenediamine) -μ - Aquodicobalt(II)}}</ref> |
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==See also== |
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*]s, a structurally related class of ] |
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==References== |
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==References== |
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