Dynamic axial ligand-site exchange in facially discriminated ruthenium(II) carbonyl and rhodium(III) halide metalloporphyrins

Inorganic Chemistry

Volumn 46, Issue 12, 2007, Pages 4876-4886

  Gunter, Maxwell J ^a   Mullen, Kathleen M ^a  

^a UNIVERSITY OF NEW ENGLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; METALLOPORPHYRIN; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; RHODIUM; RUTHENIUM DERIVATIVE;

ARTICLE; CHEMISTRY;

LIGANDS; METALLOPORPHYRINS; ORGANOMETALLIC COMPOUNDS; PYRIDINES; RHODIUM; RUTHENIUM COMPOUNDS;

EID: 34347240386     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic062112i     Document Type: Article

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61. A distinction needs to be made between inherent facial discrimination in a structurally asymmetric porphyrin such as 1 or 4 and the inevitable facial discrimination that results from two different axial ligands at the metal center. For example, a MP(X)L complex will have facial distinction, although the free-base porphyrin need not, as is the case for peripherally substituted flat porphyrin derivatives such as 5.
62. The weaker binding and lability of zinc porphyrins renders them less suitable in this design motif.
63. Sanders and Redman (Redman, J. E.; Sanders, J. K. M. Org. Letters 2000, 2, 4141-4144) have also reported atropisomerization in strapped porphyrins systems, which have chain lengths comparable to those of tetraethylene glycol straps, but with a disulfide linkage rather than a bulky naphthoquinol unit in the center; nevertheless, these too show slow equilibration of the cis and trans forms (1 h in refluxing toluene).
64. It is not immediately apparent why the more-stable binding site for this bulky ligand is in the inside position, but π-π interactions between the aromatic groups of the ligand and the naphthoquinol or hydroquinol units may be a contributing factor.
65. To assist the reader in interpreting the expected relationship between the symmetry, splitting pattern, chemical shift, and integration expected for each of the Type I-V structures, Table S1 is included in the Supporting Information.
66. 20
67. in. NOE and ROESY correlations between the pyrazine and nearby ethoxy protons in the strap of the porphyrin support such a structure.
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69. 29
70. The α protons in the coordinated pyrazine are affected overwhelmingly by the porphyrin shielding in both "pz-in" and "pz-out" cases, and, hence, the shifts are not very different in either case. The β protons are more affected by the naphthoquinol in the pz-in case and, in fact, are deshielded to some extent, as a result of possible edge-to-face aromatic interactions under the naphthoquinol ring.
71. The limited range of ligand combinations tested in this study militates against a definitive rationalization of the factors involved in ligand-site preference. However, one such factor may involve electronic repulsions between the ligands and the naphthoquinol or hydroquinol units of the strap. Computed electron densities for the ligands 7, 9, 10, and pyridine indicate increased electron density in the region adjacent to the electron-rich units of the straps for 7 compared with those of 9,10, and pyridine, and this would indicate a destabilization of 7 relative to the other ligands. Calculated electrostatic potential diagrams are given in the Supporting Information, Figure S15.
72. Although we have not encountered any examples where the final outcome is an equilibrating mixture in these limiting systems, we predict that for other combinations of ligands, an equilibrium mixture of both isomers might well be present under ambient conditions.
73. in species.
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