Synthesis, Characterization, and Molecular Structures of Diethylnitrosamine Metalloporphyrin Complexes of Iron, Ruthenium, and Osmium

Chen, Li; Yi, Geun-Bae; Wang, Lisheng; Dharmawardana, Udeni R.; Dart, Amelia C.; Khan, Masood A.; Richter‐Addo, George B.

doi:10.1021/ic9801591

Cited by 36 publications

(53 citation statements)

References 94 publications

(137 reference statements)

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“…Several years ago, we reported the first such adduct between a nitrosamine and an iron porphyrin, namely the ferric high-spin complex [(TPP)Fe(ONNEt) 2 ]ClO 4 21,22. To date, this remains the only synthetic iron porphyrin nitrosamine compound in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…N -nitrosopiperidine (( cyclo -CH 2 ) 5 NNO, 99%) and N -nitrosopyrrolidine (( cyclo -CH 2 ) 4 NNO, 99%) were purchased from Fluka. [(TPP)Fe III (THF) 2 ]ClO 4 22 and N -nitrosodibenzylamine ((PhCH 2 ) 2 NNO25 were prepared by published procedures. N -ethyl- N -nitrosoaniline (Ph(Et)NNO), N -methyl- N -nitrosoaniline (Ph(Me)NNO) and the nitroso 15 N-labeled compounds Et 2 N 15 NO, ( cyclo -CH 2 ) 4 N 15 NO and (PhCH 2 ) 2 N 15 NO were prepared in a manner similar to that used to prepare the unlabeled (PhCH 2 ) 2 NNO,25 but using Na 15 NO 2 instead of NaNO 2 in the nitrosation reactions.…”

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared as previously described in reference 22. IR (NaCl, cm −1 ): υ NO/NN 1271 m; also υ ClO 4 1098 s, 1074 m, 623 m.…”

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared as described previously in reference 22 (i.e., by Method I above). Yield: 39%.…”

Section: Methodsmentioning

confidence: 99%

“…The binding mode B was established in 1980 for a Pd complex of the form Pd{N(O)N(Me)C 6 H 4 }Cl(PPh 3 ) 19. Although binding mode C had been proposed for a series of Lewis acid adducts of nitrosamines (based on IR and 1 H NMR spectroscopy),20 no metal-nitrosamine complex with this binding mode was reported until our preparation and crystallization in 1995 of a diethylnitrosamine adduct of a ferric porphyrin, namely [(TPP)Fe(ONNEt 2 ) 2 ]ClO 4 (TPP = tetraphenylporphyrinato dianion) 21,22. Recently, Doctorovich and coworkers have confirmed the binding mode D (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Five- and Six-Coordinate Adducts of Nitrosamines with Ferric Porphyrins: Structural Models for the Type II Interactions of Nitrosamines with Ferric Cytochrome P450

Goodrich

Lehnert

et al. 2010

Inorg. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared as previously described in reference 22. IR (NaCl, cm −1 ): υ NO/NN 1271 m; also υ ClO 4 1098 s, 1074 m, 623 m.…”

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared as described previously in reference 22 (i.e., by Method I above). Yield: 39%.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Five- and Six-Coordinate Adducts of Nitrosamines with Ferric Porphyrins: Structural Models for the Type II Interactions of Nitrosamines with Ferric Cytochrome P450

Goodrich

Lehnert

et al. 2010

Inorg. Chem.

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Iron Porphyrin Chemistry

Walker¹,

Simonis²

2005

Encyclopedia of Inorganic Chemistry

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This article reviews most aspects of the chemistry of iron porphyrins, from Fe(0) to Fe(V), including occurrence and roles of natural iron porphyrins (hemes) and their synthetic analogs, structures and electron configurations of iron porphyrins of all oxidation and spin states, π electron configuration of the porphyrin ring, synthesis of metal‐free porphyrins and other related macrocycles, insertion of iron into free‐base porphyrins and related macrocycles, the properties, reactions, uses and biological relevance of iron(0), ‐(I), ‐(II) porphyrins (the latter with S = 0, 1, and 2 spin state possibilities), of iron(II) porphyrin π‐cation radicals, of iron(III) porphyrins (with S = 1/2, 3/2, and 5/2 spin state possibilities), of iron(III) porphyrin and corrole π‐cation radicals, of iron(IV) porphyrins (including five‐ and six‐coordinate ferryl (FeO) 2+ , iron(IV) phenyl, carbene and hydrazine complexes, and the bis‐methoxide complex) and a comparison of iron(IV) porphyrins to iron(III) porphyrin π‐cation radicals, of iron(IV) porphyrin π‐cation radicals, and of the possible existence of iron(V) porphyrins. Included in the Fe(II) part are sections on addition of ligands to four‐coordinate iron(II) porphyrins, including equilibrium binding constants, photodissociation of ligands from PFeL 2 complexes, binding of small molecules (O 2 , CO, NO, HNO) to 5‐coordinate iron(II) porphyrins and design of porphyrin ligands that will mimic the active sites of heme proteins such as myoglobin and hemoglobin, the cytochromes P450 and nitric oxide synthases, and the nitrophorins and guanylyl cyclases. Included in the iron(III) part are sections on both 5‐ and 6‐coordinate high‐spin complexes and their similarities and differences, bridged or through‐space magnetically coupled complexes of high‐spin iron(III) porphyrins with other metal complexes as possible models for cytochrome oxidase and the assimilatory sulfite reductases, coupled oxidation of hemes by hydrogen peroxide or its equivalent, and the relationship of this reactivity to the reactions of heme oxygenase, iron(III) porphyrins as reduction catalysts, and photochemistry of iron(III) porphyrins, possible electron configurations of low‐spin iron(III) porphyrins, the phenomenon and possible electronic consequences of ruffling of the porphinato core in iron(III) porphyrins, the preferred orientation of planar axial ligands bound to low‐spin iron(III) porphyrins, NO complexes of iron(III) porphyrins, reduction potentials, equilibrium constants and rates of axial‐ligand addition and exchange, kinetics of axial‐ligand rotation and porphyrin ring inversion, kinetics of reduction and autoreduction of iron(III) porphyrins, electron self‐exchange between low‐spin iron(III) and iron(II) porphyrins, synthetic ferriheme proteins, and synthesis of five‐coordinate low‐spin iron(III) porphyrins having σ‐alkyl or σ‐aryl groups as axial ligands. The iron(IV) and iron(IV) cation radical sections discuss the high‐valent states of cytochromes P450 and related enzymes.

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Interactions of Nitrosoalkanes/arenes, Nitrosamines, Nitrosothiols, and Alkyl Nitrites with Metals

Richter‐Addo

2014

Progress in Inorganic Chemistry: Volume 59

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Synthesis, Characterization, and Molecular Structures of Diethylnitrosamine Metalloporphyrin Complexes of Iron, Ruthenium, and Osmium

Cited by 36 publications

References 94 publications

Five- and Six-Coordinate Adducts of Nitrosamines with Ferric Porphyrins: Structural Models for the Type II Interactions of Nitrosamines with Ferric Cytochrome P450

Five- and Six-Coordinate Adducts of Nitrosamines with Ferric Porphyrins: Structural Models for the Type II Interactions of Nitrosamines with Ferric Cytochrome P450

Iron Porphyrin Chemistry

Interactions of Nitrosoalkanes/arenes, Nitrosamines, Nitrosothiols, and Alkyl Nitrites with Metals

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