Iron(tetraphenylporphyrinato) chloride
{{Chembox
| ImageFile = FeTPPCl.png
| ImageSize =
| ImageAlt =
| IUPACName =
| OtherNames = fecl(tpp)
|Section1={{Chembox Identifiers
| CASNo = 16456-81-8
| PubChem =
| ChemSpiderID = 21171533
| StdInChI =1S/C44H28N4.ClH.Fe/c1-5-13-29(14-6-1)41-33-21-23-35(45-33)42(30-15-7-2-8-16-30)37-25-27-39(47-37)44(32-19-11-4-12-20-32)40-28-26-38(48-40)43(31-17-9-3-10-18-31)36-24-22-34(41)46-36;;/h1-28H;1H;/q-2;;+3/p-1/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-;;
| StdInChIKey = ZDYSAMCSFRQDMN-YKKPBKTHSA-M
| SMILES = c1ccc(cc1)/c/2c\3/nc(/c(c/4\n5/c(c(\c6n/c(c(\c7n(c2cc7)[Fe]5Cl)/c8ccccc8)/C=C6)/c9ccccc9)/cc4)/c1ccccc1)C=C3
}}
|Section2={{Chembox Properties
| C=44|H=28|N=4|Cl=1|Fe=1
| MolarMass =
| Appearance = dark blue solid
| Density = 1.318 g/cm3
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
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Iron(tetraporphyrinato) chloride is the coordination complex with the formula Fe(TPP)Cl where TPP is the dianion [C44H28N4]2-. The compound forms blue microcrystals that dissolve in chlorinated solvent to give brown solutions. In terms of structure, the complex is five-coordinate with idealized C4v point group symmetry.{{cite journal|doi=10.1021/ic5015835|title=Intermolecular Interactions in Solid-State Metalloporphyrins and Their Impacts on Crystal and Molecular Structures|year=2014|last1=Hunter|first1=Seth C.|last2=Smith|first2=Brenda A.|last3=Hoffmann|first3=Christina M.|last4=Wang|first4=Xiaoping|last5=Chen|first5=Yu-Sheng|last6=McIntyre|first6=Garry J.|last7=Xue|first7=Zi-Ling|journal=Inorganic Chemistry|volume=53|issue=21|pages=11552–11562|pmid=25338536}} It is one of more common transition metal porphyrin complexes.
Synthesis and reactions
Fe(TPP)Cl is prepared by the reaction of tetraphenylporphyrin (H2TPP) and ferrous chloride in the presence of air:
:H2TPP + FeCl2 + 1/4 O2 → Fe(TPP)Cl + HCl + 1/2 H2O
The chloride can be replaced with other halides and pseudohalides. Base gives the "mu-oxo dimer":
:2 Fe(TPP)Cl + 2 NaOH → [Fe(TPP)]2O + 2 NaCl + H2O
Most relevant to catalysis, the complex is easily reduced to give ferrous derivatives (L = pyridine, imidazole):
:Fe(TPP)Cl + e- + 2 L → Fe(TPP)L2 + Cl−
The complex is widely studied as a catalyst.{{cite book|doi=10.1002/047084289X.rn01388|chapter=Iron(III)meso-Tetraphenylporphine Chloride|title=Encyclopedia of Reagents for Organic Synthesis|year=2012|last1=Cui|first1=Xin|last2=Zhang|first2=X. Peter|isbn=978-0471936237}}{{cite journal|doi=10.1021/jacs.9b02640|title=Mechanism of Catalytic O2 Reduction by Iron Tetraphenylporphyrin|year=2019|last1=Pegis|first1=M. L.|last2=Martin|first2=D. J.|last3=Wise|first3=C. F.|last4=Brezny|first4=A. C.|last5=Johnson|first5=S. I.|last6=Johnson|first6=L. E.|last7=Kumar|first7=N.|last8=Raugei|first8=S.|last9=Mayer|first9=J. M.|journal=Journal of the American Chemical Society|volume=141|issue=20|pages=8315–8326|pmid=31042028|pmc=6684231}}