Site-selective formation of an iron(iv)–oxo species at the more electron-rich iron atom of heteroleptic μ-nitrido diiron phthalocyanines

A combination of MS and computation on μ-nitrido bridged diiron complexes reveals H2O2 binding to the complex and generates an oxidant capable of oxidizing methane.

[1]  Jing Zhang,et al.  Drug metabolism by cytochrome p450 enzymes: what distinguishes the pathways leading to substrate hydroxylation over desaturation? , 2015, Chemistry.

[2]  P. Sautet,et al.  In Silico Screening of Iron-Oxo Catalysts for CH Bond Cleavage , 2015 .

[3]  S. P. Rath,et al.  Spin-state ordering in hydroxo-bridged diiron(III)bisporphyrin complexes. , 2015, Inorganic chemistry.

[4]  M. Crestoni,et al.  A comprehensive test set of epoxidation rate constants for iron(iv)–oxo porphyrin cation radical complexes , 2014, Chemical science.

[5]  Matthew G. Quesne,et al.  Differences and Comparisons of the Properties and Reactivities of Iron(III)–hydroperoxo Complexes with Saturated Coordination Sphere , 2014, Chemistry.

[6]  S. D. de Visser,et al.  Long-range electron transfer triggers mechanistic differences between iron(IV)-oxo and iron(IV)-imido oxidants. , 2014, Journal of the American Chemical Society.

[7]  V. Briois,et al.  X-ray absorption and emission spectroscopies of X-bridged diiron phthalocyanine complexes (FePc)2X (X = C, N, O) combined with DFT study of (FePc)2X and their high-valent diiron oxo complexes. , 2014, Inorganic chemistry.

[8]  V. Nemykin,et al.  Binuclear iron(III) octakis(perfluorophenyl)tetraazaporphyrin μ-oxodimer: a highly efficient catalyst for biomimetic oxygenation reactions , 2014 .

[9]  F. Pfaff,et al.  Status of reactive non-heme metal-oxygen intermediates in chemical and enzymatic reactions. , 2014, Journal of the American Chemical Society.

[10]  S. DeBeer,et al.  Dramatic Influence of an Anionic Donor on the Oxygen-Atom Transfer Reactivity of a MnV–Oxo Complex , 2014, Chemistry.

[11]  E. P. Talsi,et al.  Active sites and mechanisms of bioinspired oxidation with H2O2, catalyzed by non-heme Fe and related Mn complexes , 2014 .

[12]  P. Afanasiev,et al.  Catalytic defluorination of perfluorinated aromatics under oxidative conditions using N-bridged diiron phthalocyanine. , 2014, Journal of the American Chemical Society.

[13]  V. Ahsen,et al.  N-Bridged Dimers of Tetrapyrroles Complexed by Transition Metals: Syntheses, Characterization Methods, and Uses as Oxidation Catalysts , 2014 .

[14]  S. Fukuzumi,et al.  Tuning reactivity and mechanism in oxidation reactions by mononuclear nonheme iron(IV)-oxo complexes. , 2014, Accounts of chemical research.

[15]  P. Maldivi,et al.  A diiron(III,IV) imido species very active in nitrene-transfer reactions. , 2014, Angewandte Chemie.

[16]  Matthew G. Quesne,et al.  Computational modelling of oxygenation processes in enzymes and biomimetic model complexes. , 2014, Chemical communications.

[17]  Matthew G. Quesne,et al.  Quantum mechanics/molecular mechanics study on the oxygen binding and substrate hydroxylation step in AlkB repair enzymes. , 2014, Chemistry.

[18]  S. D. de Visser,et al.  Comparison of the reactivity of nonheme iron(IV)-oxo versus iron(IV)-imido complexes: which is the better oxidant? , 2013, Angewandte Chemie.

[19]  Ümit Işci.  The first push-pull μ-nitrido iron phthalocyanine dimer , 2013 .

[20]  F. Neese,et al.  Iron Azides with Cyclam-Derived Ligands: Are They Precursors for High-Valent Iron Nitrides in the Gas Phase? , 2013, ChemPlusChem.

[21]  A. Sorokin.  Phthalocyanine metal complexes in catalysis. , 2013, Chemical reviews.

[22]  S. D. de Visser,et al.  Does hydrogen-bonding donation to manganese(IV)-oxo and iron(IV)-oxo oxidants affect the oxygen-atom transfer ability? A computational study. , 2013, Chemistry.

[23]  S. P. Visser,et al.  Intrinsic properties and reactivities of mononuclear nonheme iron-oxygen complexes bearing the tetramethylcyclam ligand , 2013 .

[24]  P. Afanasiev,et al.  An N-bridged high-valent diiron-oxo species on a porphyrin platform that can oxidize methane. , 2012, Nature chemistry.

[25]  J. Groves,et al.  Detection and kinetic characterization of a highly reactive heme-thiolate peroxygenase compound I. , 2012, Journal of the American Chemical Society.

[26]  E. P. Talsi,et al.  Chemo- and stereoselective CH oxidations and epoxidations/cis-dihydroxylations with H2O2, catalyzed by non-heme iron and manganese complexes , 2012 .

[27]  H. Fujii,et al.  Effect of the axial ligand on the reactivity of the oxoiron(IV) porphyrin π-cation radical complex: higher stabilization of the product state relative to the reactant state. , 2012, Inorganic chemistry.

[28]  D. Schröder.  Applications of electrospray ionization mass spectrometry in mechanistic studies and catalysis research. , 2012, Accounts of chemical research.

[29]  V. Briois,et al.  Generation and characterization of high-valent iron oxo phthalocyanines. , 2012, Chemical communications.

[30]  P. Glatzel,et al.  Study of N-bridged diiron phthalocyanine relevant to methane oxidation: Insight into oxidation and spin states from high resolution 1s core hole X-ray spectroscopy , 2012 .

[31]  M. Costas.  Selective C–H oxidation catalyzed by metalloporphyrins , 2011 .

[32]  Jennifer S. Mathieson,et al.  Observation of Fe(V)=O using variable-temperature mass spectrometry and its enzyme-like C-H and C=C oxidation reactions. , 2011, Nature chemistry.

[33]  S. D. de Visser,et al.  Nonheme ferric hydroperoxo intermediates are efficient oxidants of bromide oxidation. , 2011, Chemical communications.

[34]  P. Afanasiev,et al.  Solvent-dependent rotational phenomena in μ-nitrido-[2,3,9,10,16,17,23,24-octa(n-pentoxy)phthalocyaninato]diiron complex , 2011 .

[35]  H. Fujii,et al.  Redox potentials of oxoiron(IV) porphyrin π-cation radical complexes: participation of electron transfer process in oxygenation reactions. , 2011, Inorganic chemistry.

[36]  E. P. Talsi,et al.  EPR, 1H and 2H NMR, and reactivity studies of the iron-oxygen intermediates in bioinspired catalyst systems. , 2011, Inorganic chemistry.

[37]  S. Makarov,et al.  Redox non-innocence of a nitrido bridge in a methane-activating dimer of iron phthalocyanine , 2011 .

[38]  G. Grogan.  Cytochromes P450: exploiting diversity and enabling application as biocatalysts. , 2011, Current opinion in chemical biology.

[39]  X. Zhang,et al.  Catalytic C-H functionalization by metalloporphyrins: recent developments and future directions. , 2011, Chemical Society reviews.

[40]  C. Pollock,et al.  Valence-to-core X-ray emission spectroscopy: a sensitive probe of the nature of a bound ligand. , 2011, Journal of the American Chemical Society.

[41]  S. de Vries,et al.  Spectroscopic characterization of cytochrome P450 Compound I. , 2011, Archives of biochemistry and biophysics.

[42]  N. Turner,et al.  Cytochromes P450 as useful biocatalysts: addressing the limitations. , 2011, Chemical communications.

[43]  P. Afanasiev,et al.  High-valent diiron species generated from N-bridged diiron phthalocyanine and H(2)O(2). , 2011, Dalton transactions.

[44]  Frank Neese,et al.  Nonheme oxo-iron(IV) intermediates form an oxyl radical upon approaching the C–H bond activation transition state , 2011, Proceedings of the National Academy of Sciences.

[45]  S. P. Visser,et al.  Iron-containing enzymes : versatile catalysts of hydroxylation reactions in nature , 2011 .

[46]  S. P. Rath,et al.  A remarkably bent diiron(III)-μ-hydroxo bisporphyrin: unusual stabilization of two spin states of iron in a single molecular framework. , 2010, Journal of the American Chemical Society.

[47]  P. Afanasiev,et al.  Oxidation of methane and ethylene in water at ambient conditions , 2010 .

[48]  Michael T. Green,et al.  Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics , 2010, Science.

[49]  V. Ahsen,et al.  Preparation of N-bridged diiron phthalocyanines bearing bulky or small electron-withdrawing substituents , 2010 .

[50]  J. Valentine,et al.  A biomimetic ferric hydroperoxo porphyrin intermediate. , 2010, Angewandte Chemie.

[51]  P. R. Montellano.  Hydrocarbon hydroxylation by cytochrome P450 enzymes. , 2010 .

[52]  Sam P. de Visser,et al.  Trends in substrate hydroxylation reactions by heme and nonheme iron(IV)-oxo oxidants give correlations between intrinsic properties of the oxidant with barrier height , 2010 .

[53]  V. Nemykin,et al.  Binuclear Iron(III) Phthalocyanine(μ-Oxodimer)-Catalyzed Oxygenation of Aromatic Hydrocarbons with Iodosylbenzene Sulfate and Iodosylbenzene as the Oxidants , 2009 .

[54]  P. Afanasiev,et al.  Stable N-bridged diiron (IV) phthalocyanine cation radical complexes: synthesis and properties. , 2009, Dalton transactions.

[55]  S. D. de Visser,et al.  Effect of porphyrin ligands on the regioselective dehydrogenation versus epoxidation of olefins by oxoiron(IV) mimics of cytochrome P450. , 2009, The journal of physical chemistry. A.

[56]  V. Ahsen,et al.  Preparation and characterization of mu-nitrido diiron phthalocyanines with electron-withdrawing substituents: application for catalytic aromatic oxidation. , 2009, Dalton transactions.

[57]  M. Bagherzadeh,et al.  Origin of the correlation of the rate constant of substrate hydroxylation by nonheme iron(IV)-oxo complexes with the bond-dissociation energy of the C-H bond of the substrate. , 2009, Chemistry.

[58]  C. Che,et al.  Metalloporphyrin-based oxidation systems: from biomimetic reactions to application in organic synthesis. , 2009, Chemical Communications.

[59]  M. Sutcliffe,et al.  Quantum mechanics/molecular mechanics studies on the sulfoxidation of dimethyl sulfide by compound I and compound 0 of cytochrome P450: which is the better oxidant? , 2009, The journal of physical chemistry. A.

[60]  J. Cornil,et al.  Metal-Free Phthalocyanines Bearing Eight Alkylsulfonyl Substituents: Design, Synthesis, Electronic Structure, and Mesomorphism of New Electron-Deficient Mesogens , 2009 .

[61]  H. Fujii,et al.  Catalytic reactivity of a meso-N-substituted corrole and evidence for a high-valent iron-oxo species. , 2009, Journal of the American Chemical Society.

[62]  G. van Koten,et al.  Mononuclear non-heme iron enzymes with the 2-His-1-carboxylate facial triad: recent developments in enzymology and modeling studies. , 2008, Chemical Society reviews.

[63]  W. Tolman,et al.  Biologically inspired oxidation catalysis , 2008, Nature.

[64]  S. D. de Visser,et al.  Is the bound substrate in nitric oxide synthase protonated or neutral and what is the active oxidant that performs substrate hydroxylation? , 2008, Journal of the American Chemical Society.

[65]  L. Que,et al.  Proton- and reductant-assisted dioxygen activation by a nonheme iron(II) complex to form an oxoiron(IV) intermediate. , 2008, Angewandte Chemie.

[66]  A. Sorokin,et al.  N-bridged diiron phthalocyanine catalyzes oxidation of benzene with H2O2 via benzene oxide with NIH shift evidenced by using 1,3,5-[D3]benzene as a probe. , 2008, Chemistry.

[67]  S. Shaik,et al.  A valence bond modeling of trends in hydrogen abstraction barriers and transition states of hydroxylation reactions catalyzed by cytochrome P450 enzymes. , 2008, Journal of the American Chemical Society.

[68]  S. Sligar,et al.  X-ray absorption spectroscopic characterization of a cytochrome P450 compound II derivative , 2008, Proceedings of the National Academy of Sciences.

[69]  T. Bugg,et al.  Non-heme iron-dependent dioxygenases: unravelling catalytic mechanisms for complex enzymatic oxidations. , 2008, Current opinion in chemical biology.

[70]  A. Sorokin,et al.  Bio-inspired oxidation of methane in water catalyzed by N-bridged diiron phthalocyanine complex. , 2008, Chemical communications.

[71]  I. Korendovych,et al.  Dioxygen activation at non-heme iron: insights from rapid kinetic studies. , 2007, Accounts of chemical research.

[72]  W. Nam,et al.  High-valent iron(IV)-oxo complexes of heme and non-heme ligands in oxygenation reactions. , 2007, Accounts of chemical research.

[73]  Arani Chanda,et al.  Chemical and Spectroscopic Evidence for an FeV-Oxo Complex , 2007, Science.

[74]  S. Shaik,et al.  The Poulos-Kraut mechanism of Compound I formation in horseradish peroxidase: a QM/MM study. , 2006, The journal of physical chemistry. B.

[75]  C. Krebs,et al.  Stalking intermediates in oxygen activation by iron enzymes: motivation and method. , 2006, Journal of inorganic biochemistry.

[76]  Sam P. de Visser,et al.  Differences in and Comparison of the Catalytic Properties of Heme and Non-Heme Enzymes with a Central Oxo–Iron Group† , 2006 .

[77]  W. Nam,et al.  A Thiolate-Ligated Nonheme Oxoiron(IV) Complex Relevant to Cytochrome P450 , 2005, Science.

[78]  Rui Zhang,et al.  Photochemical generation of a highly reactive iron-oxo intermediate. A true iron(V)-oxo species? , 2005, Journal of the American Chemical Society.

[79]  S. V. Kryatov,et al.  Kinetics and mechanisms of formation and reactivity of non-heme iron oxygen intermediates. , 2005, Chemical reviews.

[80]  Ilme Schlichting,et al.  Structure and chemistry of cytochrome P450. , 2005, Chemical reviews.

[81]  M. Abu‐Omar,et al.  Reaction mechanisms of mononuclear non-heme iron oxygenases. , 2005, Chemical reviews.

[82]  Uwe Bergmann,et al.  High resolution 1s core hole X-ray spectroscopy in 3d transition metal complexes—electronic and structural information , 2005 .

[83]  Sason Shaik,et al.  Mechanism of oxidation reactions catalyzed by cytochrome p450 enzymes. , 2004, Chemical reviews.

[84]  H. Gray,et al.  Oxidations Catalyzed by Metallocorroles , 2004 .

[85]  L. Que,et al.  Dioxygen activation at mononuclear nonheme iron active sites: enzymes, models, and intermediates. , 2004, Chemical reviews.

[86]  S. Lippard,et al.  Synthetic models for non-heme carboxylate-bridged diiron metalloproteins: strategies and tactics. , 2004, Chemical reviews.

[87]  Sason Shaik,et al.  Active species of horseradish peroxidase (HRP) and cytochrome P450: two electronic chameleons. , 2003, Journal of the American Chemical Society.

[88]  J. Groves.  The bioinorganic chemistry of iron in oxygenases and supramolecular assemblies , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[89]  Mi Hee Lim,et al.  Crystallographic and spectroscopic characterization of a nonheme Fe(IV)-O complex. , 2003, Science.

[90]  T. Bugg.  Oxygenases: mechanisms and structural motifs for O(2) activation. , 2001, Current opinion in chemical biology.

[91]  Vazquez,et al.  Synthesis of novel push-pull unsymmetrically substituted alkynyl phthalocyanines , 2000, The Journal of organic chemistry.

[92]  A. Trautwein,et al.  Generation of oxoiron(IV) tetramesitylporphyrin π-cation radical complexes by m-CPBA oxidation of ferric tetramesitylporphyrin derivatives in butyronitrile at −78 °C. Evidence for the formation of six-coordinate oxoiron(IV) tetramesitylporphyrin π-cation radical complexes FeIV=O(tmp)X (X=Cl−, Br−), , 2000 .

[93]  W. Scheidt,et al.  Molecular Structure of an Fe(IV) Species: {[Fe(TTP)]2N}SbCl6 , 2000 .

[94]  Mindy I. Davis,et al.  Geometric and electronic structure/function correlations in non-heme iron enzymes. , 2000, Chemical reviews.

[95]  Michael T. Green.  Evidence for Sulfur-Based Radicals in Thiolate Compound I Intermediates , 1999 .

[96]  T. Torres,et al.  Synthesis of Novel Unsymmetrically Substituted Push-Pull Phthalocyanines , 1996 .

[97]  J. Dawson,et al.  Heme-Containing Oxygenases. , 1996, Chemical reviews.

[98]  G. Trigiante,et al.  (.mu.-Nitrido)((tetraphenylporphyrinato)iron)((phthalocyaninato)iron) and Its Fe-Ru Analog: Redox Behavior and Characterization of New Fe(IV)-Containing Species. X-ray Crystal Structure of [(THF)(TPP)Fe-N-FePc(H2O)](I5).cntdot.2THF , 1995 .

[99]  A. G. Gürek,et al.  Octakis(alkylthio)-substituted phthalocyanines and their interactions with silver(I) and palladium(II) ions , 1994 .

[100]  G. Rossi,et al.  First example of a mixed-ligand bimetallic (Fe-Fe) N-bridged dimer: (.mu.-nitrido)[((tetraphenylporphyrinato)iron)(phthalocyaninato)iron] , 1993 .

[101]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[102]  A. Becke,et al.  Density-functional exchange-energy approximation with correct asymptotic behavior. , 1988, Physical review. A, General physics.

[103]  A. Gold,et al.  Oxoferryl complexes of the halogenated (porphinato)iron catalyst [tetrakis(2,6-dichlorophenyl)porphinato]iron , 1988 .

[104]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[105]  G. Rossi,et al.  High-valent iron phthalocyanine .mu.-nitrido dimers , 1988 .

[106]  J. Perdew,et al.  Density-functional approximation for the correlation energy of the inhomogeneous electron gas. , 1986, Physical review. B, Condensed matter.

[107]  L. Bottomley,et al.  Spectroelectrochemistry of a .mu.-nitrido-bridged iron phthalocyanine dimer , 1985 .

[108]  W. Ansorge,et al.  Transcytosis of the G protein of vesicular stomatitis virus after implantation into the apical plasma membrane of Madin-Darby canine kidney cells. I. Involvement of endosomes and lysosomes , 1984, The Journal of cell biology.

[109]  W. R. Wadt,et al.  Ab initio effective core potentials for molecular calculations , 1984 .

[110]  V. Herzog.  Transcytosis in thyroid follicle cells , 1983, The Journal of cell biology.

[111]  S. Shiraishi,et al.  SYNTHESIS OF METALLOPHTHALOCYANINES FROM PHTHALONITRILE WITH STRONG ORGANIC BASES , 1983 .

[112]  C. Hsu,et al.  Contribution of oligosaccharide sulfation to the charge heterogeneity of a viral glycoprotein. , 1982, The Journal of biological chemistry.

[113]  L. Kääriäinen,et al.  Incomplete complex oligosaccharides in semliki forest virus envelope proteins arrested within the cell in the presence of monensin. , 1982, Journal of molecular biology.

[114]  B. Posner,et al.  Internalization of insulin into rat liver Golgi elements. Evidence for vesicle heterogeneity and the path of intracellular processing. , 1982, The Journal of biological chemistry.

[115]  D. Abrahamson,et al.  Evidence for the sorting of endocytic vesicle contents during the receptor-mediated transport of IgG across the newborn rat intestine , 1981, The Journal of cell biology.

[116]  R. Haushalter,et al.  High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450 , 1981 .

[117]  S. Singer,et al.  Passage of an integral membrane protein, the vesicular stomatitis virus glycoprotein, through the Golgi apparatus en route to the plasma membrane. , 1981, Proceedings of the National Academy of Sciences of the United States of America.

[118]  E. Boulan,et al.  Polarized distribution of viral envelope proteins in the plasma membrane of infected epithelial cells , 1980, Cell.

[119]  M. Roth,et al.  Polarity of influenza and vesicular stomatitis virus maturation in MDCK cells: lack of a requirement for glycosylation of viral glycoproteins. , 1979, Proceedings of the National Academy of Sciences of the United States of America.

[120]  D. Fiete,et al.  Structural determinants of Ricinus communis agglutinin and toxin specificity for oligosaccharides. , 1979, The Journal of biological chemistry.

[121]  C. Ballou,et al.  Carbohydrate structure of vesicular stomatitis virus glycoprotein. , 1978, The Journal of biological chemistry.

[122]  S. Kornfeld,et al.  Deficient uridine diphosphate-N-acetylglucosamine:glycoprotein N-acetylglucosaminyltransferase activity in a clone of Chinese hamster ovary cells with altered surface glycoproteins. , 1975, The Journal of biological chemistry.

[123]  J. Pople,et al.  Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules , 1972 .

[124]  Matthew G. Quesne,et al.  Proceedings of the Chemical Society. June 1958 , 1958 .