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Iron(tetraphenylporphyrinato) chloride

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Iron(tetraphenylporphyrinato) chloride
Names
Other names fecl(tpp)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
InChI
  • InChI=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-;;Key: ZDYSAMCSFRQDMN-YKKPBKTHSA-M
SMILES
  • c1ccc(cc1)/c/2c\3/nc(/c(c/4\n5/c(c(\c6n/c(c(\c7n(c2cc7)5Cl)/c8ccccc8)/C=C6)/c9ccccc9)/cc4)/c1ccccc1)C=C3
Properties
Chemical formula C44H28ClFeN4
Molar mass 704.03 g·mol
Appearance dark blue solid
Density 1.318 g/cm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Iron(tetraporphyrinato) chloride is the coordination complex with the formula Fe(TPP)Cl where TPP is the dianion . 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. 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 → 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.

References

  1. Hunter, Seth C.; Smith, Brenda A.; Hoffmann, Christina M.; Wang, Xiaoping; Chen, Yu-Sheng; McIntyre, Garry J.; Xue, Zi-Ling (2014). "Intermolecular Interactions in Solid-State Metalloporphyrins and Their Impacts on Crystal and Molecular Structures". Inorganic Chemistry. 53 (21): 11552–11562. doi:10.1021/ic5015835. PMID 25338536.
  2. Cui, Xin; Zhang, X. Peter (2012). "Iron(III)meso-Tetraphenylporphine Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01388. ISBN 978-0471936237.
  3. Pegis, M. L.; Martin, D. J.; Wise, C. F.; Brezny, A. C.; Johnson, S. I.; Johnson, L. E.; Kumar, N.; Raugei, S.; Mayer, J. M. (2019). "Mechanism of Catalytic O2 Reduction by Iron Tetraphenylporphyrin". Journal of the American Chemical Society. 141 (20): 8315–8326. doi:10.1021/jacs.9b02640. PMC 6684231. PMID 31042028.
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