Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes

Strautmann J, Dammers S, Limpke T, Parthier J, Zimmermann T, Walleck S, Heinze-Brückner G, Stammler A, Bögge H, Glaser T (2016)
DALTON TRANSACTIONS 45(8): 3340-3361.

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Abstract / Bemerkung
Based on a rational ligand design for stabilizing high-valent {Fe(mu-O)(2)Fe} cores, a new family of dinucleating bis(tetradentate) ligands with varying terminal donor functions has been developed: redox-inert biomimetic carboxylates in H(4)julia, pyridines in susan, and phenolates in H(4)hilde(Me2). Based on a retrosynthetic analysis, the ligands were synthesized and used for the preparation of their diferric complexes [(julia){Fe(OH2)(mu-O)Fe(OH2)}]center dot 6H(2)O, [(julia){Fe(OH2)(mu-O)Fe(OH2)}]center dot 7H(2)O, [(julia){Fe(DMSO)(mu-O)Fe(DMSO)}]center dot 3DMSO, [(hilde(Me2)){Fe(mu-O)Fe}]center dot CH2Cl2, [(hilde(Me2)){FeCl}(2)]center dot 2CH(2)Cl(2), [(susan){FeCl(mu-O)FeCl}]Cl-2 center dot 2H(2)O, [(susan){FeCl(mu-O)FeCl0.75(OCH3)(0.25)}](ClO4)(2)center dot 0.5MeOH, and [(susan){FeCl(mu-O)FeCl}](ClO4)(2)center dot 0.5EtOH, which were characterized by single-crystal X-ray diffraction, FTIR, UV-Vis-NIR, Massbauer, magnetic, and electrochemical measurements. The strongly electron-donating phenolates afford five-coordination, while the carboxylates and pyridines lead to six-coordination. The analysis of the ligand conformations demonstrates a strong flexibility of the ligand backbone in the complexes. The different hydrogen-bonding in the secondary coordination sphere of [(julia){Fe(OH2)(mu-O)Fe(OH2)}] influences the C-O, C=O, and Fe-O bond lengths and is reflected in the FTIR spectra. The physical properties of the central {Fe(mu-O)Fe} core (d-d, mu-oxo -> Fe-III CT, nu(as)(Fe-O-Fe), J) are governed by the differences in terminal ligands - Fe-III bonds: strongly covalent pi-donation with phenolates, less covalent pi-donation with carboxylates, and pi-acceptation with pyridines. Thus, [(susan){FeCl(mu-O)FeCl}](2+) is oxidized at 1.48 V vs. Fc(+)/Fc, which is shifted to 1.14 V vs. Fc(+)/Fc by methanolate substitution, while [(julia){Fe(OH2)(mu-O) Fe(OH2)}] is oxidized <= 1 V vs. Fc(+)/Fc. [(hilde(Me2)){Fe(mu-O)Fe}] is oxidized at 0.36 V vs. Fc(+)/Fc to a phenoxyl radical. The catalytic oxidation of cyclohexane with TONs up to 39.5 and 27.0 for [(susan){FeCl(mu-O)FeCl}](2+) and [(hilde(Me2)){Fe(mu-O)Fe}], respectively, indicates the potential to form oxidizing intermediates.
Erscheinungsjahr
2016
Zeitschriftentitel
DALTON TRANSACTIONS
Band
45
Ausgabe
8
Seite(n)
3340-3361
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2902133

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Strautmann J, Dammers S, Limpke T, et al. Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes. DALTON TRANSACTIONS. 2016;45(8):3340-3361.
Strautmann, J., Dammers, S., Limpke, T., Parthier, J., Zimmermann, T., Walleck, S., Heinze-Brückner, G., et al. (2016). Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes. DALTON TRANSACTIONS, 45(8), 3340-3361. doi:10.1039/c5dt03711e
Strautmann, Julia, Dammers, Susanne, Limpke, Thomas, Parthier, Janine, Zimmermann, Thomas, Walleck, Stephan, Heinze-Brückner, Gabriele, Stammler, Anja, Bögge, Hartmut, and Glaser, Thorsten. 2016. “Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes”. DALTON TRANSACTIONS 45 (8): 3340-3361.
Strautmann, J., Dammers, S., Limpke, T., Parthier, J., Zimmermann, T., Walleck, S., Heinze-Brückner, G., Stammler, A., Bögge, H., and Glaser, T. (2016). Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes. DALTON TRANSACTIONS 45, 3340-3361.
Strautmann, J., et al., 2016. Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes. DALTON TRANSACTIONS, 45(8), p 3340-3361.
J. Strautmann, et al., “Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes”, DALTON TRANSACTIONS, vol. 45, 2016, pp. 3340-3361.
Strautmann, J., Dammers, S., Limpke, T., Parthier, J., Zimmermann, T., Walleck, S., Heinze-Brückner, G., Stammler, A., Bögge, H., Glaser, T.: Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes. DALTON TRANSACTIONS. 45, 3340-3361 (2016).
Strautmann, Julia, Dammers, Susanne, Limpke, Thomas, Parthier, Janine, Zimmermann, Thomas, Walleck, Stephan, Heinze-Brückner, Gabriele, Stammler, Anja, Bögge, Hartmut, and Glaser, Thorsten. “Design and synthesis of a dinucleating ligand system with varying terminal donor functions that provides no bridging donor and its application to the synthesis of a series of Fe-III-mu-O-Fe-III complexes”. DALTON TRANSACTIONS 45.8 (2016): 3340-3361.

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129 References

Daten bereitgestellt von Europe PubMed Central.

Biologically inspired oxidation catalysis.
Que L Jr, Tolman WB., Nature 455(7211), 2008
PMID: 18800132
The biology and chemistry of high-valent iron-oxo and iron-nitrido complexes.
Hohenberger J, Ray K, Meyer K., Nat Commun 3(), 2012
PMID: 22395611
Oxidation of methane by a biological dicopper centre.
Balasubramanian R, Smith SM, Rawat S, Yatsunyk LA, Stemmler TL, Rosenzweig AC., Nature 465(7294), 2010
PMID: 20410881
Bis(mu-oxo)dimetal "diamond" cores in copper and iron complexes relevant to biocatalysis.
Que L Jr, Tolman WB., Angew. Chem. Int. Ed. Engl. 41(7), 2002
PMID: 12491240
Status of reactive non-heme metal-oxygen intermediates in chemical and enzymatic reactions.
Ray K, Pfaff FF, Wang B, Nam W., J. Am. Chem. Soc. 136(40), 2014
PMID: 25215462
An Fe2IVO2 diamond core structure for the key intermediate Q of methane monooxygenase.
Shu L, Nesheim JC, Kauffmann K, Munck E, Lipscomb JD, Que L Jr., Science 275(5299), 1997
PMID: 8999792
Dioxygen activation in soluble methane monooxygenase.
Tinberg CE, Lippard SJ., Acc. Chem. Res. 44(4), 2011
PMID: 21391602
Geometric and electronic structure/function correlations in non-heme iron enzymes.
Solomon EI, Brunold TC, Davis MI, Kemsley JN, Lee SK, Lehnert N, Neese F, Skulan AJ, Yang YS, Zhou J., Chem. Rev. 100(1), 2000
PMID: 11749238

Lee, J. Am. Chem. Soc. 115(), 1993
Dioxygen Activation by Enzymes Containing Binuclear Non-Heme Iron Clusters.
Wallar BJ, Lipscomb JD., Chem. Rev. 96(7), 1996
PMID: 11848839

Liu, J. Am. Chem. Soc. 117(), 1995
Kinetics and mechanisms of formation and reactivity of non-heme iron oxygen intermediates.
Kryatov SV, Rybak-Akimova EV, Schindler S., Chem. Rev. 105(6), 2005
PMID: 15941212
The road to non-heme oxoferryls and beyond.
Que L Jr., Acc. Chem. Res. 40(7), 2007
PMID: 17595051

Lee, J. Am. Chem. Soc. 121(), 1999

Das, Eur. J. Inorg. Chem. 2015(), 2015
A new chiral diiron catalyst for enantioselective epoxidation.
Marchi-Delapierre C, Jorge-Robin A, Thibon A, Menage S., Chem. Commun. (Camb.) (11), 2006
PMID: 17347727

Ookubo, J. Am. Chem. Soc. 118(), 1996
Structural and spectroscopic characterization of (mu-hydroxo or mu-oxo)(mu-peroxo)diiron(III) complexes: models for peroxo intermediates of non-heme diiron proteins.
Zhang X, Furutachi H, Fujinami S, Nagatomo S, Maeda Y, Watanabe Y, Kitagawa T, Suzuki M., J. Am. Chem. Soc. 127(3), 2005
PMID: 15656607
Mixed-valent [FeIV(mu-O)(mu-carboxylato)2FeIII]3+ core.
Slep LD, Mijovilovich A, Meyer-Klaucke W, Weyhermuller T, Bill E, Bothe E, Neese F, Wieghardt K., J. Am. Chem. Soc. 125(50), 2003
PMID: 14664603

Ménage, Angew. Chem., Int. Ed. Engl. 35(), 1996

Ménage, J. Am. Chem. Soc. 120(), 1998
A diiron complex mediates an intramolecular aliphatic hydroxylation by various oxygen donors.
Avenier F, Dubois L, Dubourdeaux P, Latour JM., Chem. Commun. (Camb.) (4), 2004
PMID: 15654376
Mono- and dinuclear iron complexes of bis(1-methylimidazol-2-yl)ketone (bik): structure, magnetic properties, and catalytic oxidation studies.
Bruijnincx PC, Buurmans IL, Huang Y, Juhasz G, Viciano-Chumillas M, Quesada M, Reedijk J, Lutz M, Spek AL, Munck E, Bominaar EL, Klein Gebbink RJ., Inorg Chem 50(19), 2011
PMID: 21902227

Shul'pin, Adv. Synth. Catal. 346(), 2004

Tanase, J. Mol. Catal. A: Chem. 225(), 2005

Buchanan, Inorg. Chem. 33(), 1994
Redox and acid-base properties of asymmetric non-heme (hydr)oxo-bridged diiron complexes.
Jozwiuk A, Ingram AL, Powell DR, Moubaraki B, Chilton NF, Murray KS, Houser RP., Dalton Trans 43(25), 2014
PMID: 24841725
Catalytically active mu-Oxodiiron(IV) oxidants from Iron(III) and dioxygen.
Ghosh A, Tiago de Oliveira F, Yano T, Nishioka T, Beach ES, Kinoshita I, Munck E, Ryabov AD, Horwitz CP, Collins TJ., J. Am. Chem. Soc. 127(8), 2005
PMID: 15725005
A diiron center stabilized by a bis-TPA ligand as a model of soluble methane monooxygenase: predominant alkene epoxidation with H2O2.
Kodera M, Itoh M, Kano K, Funabiki T, Reglier M., Angew. Chem. Int. Ed. Engl. 44(43), 2005
PMID: 16217818

Dong, J. Am. Chem. Soc. 117(), 1995

Dong, J. Am. Chem. Soc. 117(), 1995

Dong, J. Am. Chem. Soc. 119(), 1997

Wilkinson, J. Am. Chem. Soc. 120(), 1998
A synthetic precedent for the [FeIV2(mu-O)2] diamond core proposed for methane monooxygenase intermediate Q.
Xue G, Wang D, De Hont R, Fiedler AT, Shan X, Munck E, Que L Jr., Proc. Natl. Acad. Sci. U.S.A. 104(52), 2007
PMID: 18093922
Insights into the P-to-Q conversion in the catalytic cycle of methane monooxygenase from a synthetic model system.
Xue G, Fiedler AT, Martinho M, Munck E, Que L Jr., Proc. Natl. Acad. Sci. U.S.A. 105(52), 2008
PMID: PMC2634879
Mossbauer and DFT study of the ferromagnetically coupled diiron(IV) precursor to a complex with an Fe(IV)(2)O(2) diamond core.
Martinho M, Xue G, Fiedler AT, Que L Jr, Bominaar EL, Munck E., J. Am. Chem. Soc. 131(16), 2009
PMID: 19338307

Hsu, J. Am. Chem. Soc. 121(), 1999

Hazell, Inorg. Chem. 33(), 1994

Kim, J. Am. Chem. Soc. 119(), 1997
Million-fold activation of the [Fe(2)(micro-O)(2)] diamond core for C-H bond cleavage.
Xue G, De Hont R, Munck E, Que L Jr., Nat Chem 2(5), 2010
PMID: 20414242
A synthetic model for the putative Fe(IV)(2)O(2) diamond core of methane monooxygenase intermediate Q.
Costas M, Rohde JU, Stubna A, Ho RY, Quaroni L, Munck E, Que L Jr., J. Am. Chem. Soc. 123(51), 2001
PMID: 11749564
High-valent nonheme iron. Two distinct iron(IV) species derived from a common iron(II) precursor.
Jensen MP, Costas M, Ho RY, Kaizer J, Mairata i Payeras A, Munck E, Que L Jr, Rohde JU, Stubna A., J. Am. Chem. Soc. 127(30), 2005
PMID: 16045338

Glaser, Z. Anorg. Allg. Chem. 629(), 2003
Molecular and electronic structures of mononuclear iron complexes using strongly electron-donating ligands and their oxidized forms.
Strautmann JB, George SD, Bothe E, Bill E, Weyhermuller T, Stammler A, Bogge H, Glaser T., Inorg Chem 47(15), 2008
PMID: 18582030
Highly oxidized diiron complexes: generation, spectroscopy, and stabilities.
Strautmann JB, Freiherr von Richthofen CG, DeBeer George S, Bothe E, Bill E, Glaser T., Chem. Commun. (Camb.) (19), 2009
PMID: 19532905

Heinze-Brückner, Inorg. Chim. Acta 374(), 2011
Molecular and electronic structures of dinuclear iron complexes incorporating strongly electron-donating ligands: implications for the generation of the one- and two-electron oxidized forms.
Strautmann JB, Freiherr von Richthofen CG, Heinze-Bruckner G, DeBeer S, Bothe E, Bill E, Weyhermuller T, Stammler A, Bogge H, Glaser T., Inorg Chem 50(1), 2010
PMID: 21114259

Schäfer, J. Am. Chem. Soc. 120(), 1998

Robson, Inorg. Nucl. Chem. Lett. 6(), 1970

Robson, Aust. J. Chem. 23(), 1970

Pilkington, Aust. J. Chem. 23(), 1970

Okawa, Bull. Chem. Soc. Jpn. 44(), 1971

Suzuki, Chem. Lett. (), 1981

Benzekri, Inorg. Chem. 27(), 1988

Borovik, J. Am. Chem. Soc. 112(), 1990

Atkins, J. Chem. Soc., Dalton Trans. (), 2003

Karlin, Inorg. Chem. 31(), 1992

Krebs, Inorg. Chem. 33(), 1994

Mani, Coord. Chem. Rev. 120(), 1992

Fenton, Chem. Ber./Recl. 130(), 1997

Sorrell, Tetrahedron 45(), 1989

Solomon, 2004

Lee, J. Am. Chem. Soc. 117(), 1995

Wei, Inorg. Chem. 33(), 1994
Modeling of End-On (&mgr;-Peroxo)dicopper(II) Complexes.
Comba P, Hilfenhaus P, Karlin KD., Inorg Chem 36(11), 1997
PMID: 11669865

Karlin, Acc. Chem. Res. 30(), 1997

Døssing, Acta Chem. Scand. 50(), 1996

Gullotti, Eur. J. Inorg. Chem. 2008(), 2008
Enantio-differentiating catalytic oxidation by a biomimetic trinuclear copper complex containing L-histidine residues.
Santagostini L, Gullotti M, Pagliarin R, Monzani E, Casella L., Chem. Commun. (Camb.) (17), 2003
PMID: 13678193
Copper-bispidine coordination chemistry: syntheses, structures, solution properties, and oxygenation reactivity.
Borzel H, Comba P, Hagen KS, Kerscher M, Pritzkow H, Schatz M, Schindler S, Walter O., Inorg Chem 41(21), 2002
PMID: 12377039
Electrochemical behavior and dioxygen reactivity of tripodal dinuclear copper complexes linked by unsaturated rigid spacers.
Gomila A, Le Poul N, Kerbaol JM, Cosquer N, Triki S, Douziech B, Conan F, Le Mest Y., Dalton Trans 42(6), 2013
PMID: 23104234

Hahn, Eur. J. Inorg. Chem. 2010(), 2010

Hahn, Eur. J. Inorg. Chem. 2009(), 2009

Kodera, J. Am. Chem. Soc. 121(), 1999

Kodera, Chem. Commun. (), 1996
Synthesis, characterization, and activation of thermally stable mu-1,2-peroxodiiron(III) complex.
Kodera M, Taniike Y, Itoh M, Tanahashi Y, Shimakoshi H, Kano K, Hirota S, Iijima S, Ohba M, Okawa H., Inorg Chem 40(19), 2001
PMID: 11531426

Santagostini, Tetrahedron: Asymmetry 10(), 1999

Bol, Angew. Chem., Int. Ed. Engl. 36(), 1997
Synthesis, structure, and greatly improved reversible O2 binding in a structurally modulated micro-eta 2:eta 2-peroxodicopper(II) complex with room-temperature stability.
Kodera M, Kajita Y, Tachi Y, Katayama K, Kano K, Hirota S, Fujinami S, Suzuki M., Angew. Chem. Int. Ed. Engl. 43(3), 2004
PMID: 14705090

Würtele, J. Coord. Chem. 63(), 2010
A tailor-made ligand to mimic the active site of diiron enzymes: an air-oxidized high-valent Fe(III) h.s.(μ-O)2Fe(IV) h.s. species.
Strautmann JB, Walleck S, Bogge H, Stammler A, Glaser T., Chem. Commun. (Camb.) 47(2), 2010
PMID: 21088779

Armarego, 2009
Chromophore-modified bis-naphthalimides: synthesis and antitumor activity of bis-dibenz[de,h]isoquinoline-1,3-diones.
Brana MF, Castellano JM, Perron D, Maher C, Conlon D, Bousquet PF, George J, Qian XD, Robinson SP., J. Med. Chem. 40(4), 1997
PMID: 9046334
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677

Luskin, J. Am. Chem. Soc. 78(), 1956

Dimroth, Chem. Ber. 98(), 1965

Schwarzenbach, Helv. Chim. Acta 40(), 1957

Tyeklar, J. Am. Chem. Soc. 115(), 1993
Direct influence of hydrogen-bonding on the reduction potential of a CuII center.
Glaser T, Liratzis I, Kataeva O, Frohlich R, Piacenza M, Grimme S., Chem. Commun. (Camb.) (9), 2006
PMID: 16491197
Molecular designs for controlling the local environments around metal ions.
Cook SA, Borovik AS., Acc. Chem. Res. 48(8), 2015
PMID: 26181849

Deacon, Coord. Chem. Rev. 33(), 1980

Sanders-Loehr, J. Am. Chem. Soc. 111(), 1989
Large spin differences in structurally related Fe6 molecular clusters and their magnetostructural explanation.
Canada-Vilalta C, O'Brien TA, Brechin EK, Pink M, Davidson ER, Christou G., Inorg Chem 43(18), 2004
PMID: 15332801

Weihe, J. Am. Chem. Soc. 119(), 1997

Gorun, Inorg. Chem. 30(), 1991

Gütlich, 2011

Wieghardt, Inorg. Chem. 21(), 1982

Norman, Inorg. Chem. 29(), 1990

Holz, Inorg. Chem. 32(), 1993

Schugar, J. Am. Chem. Soc. 94(), 1972

Reem, J. Am. Chem. Soc. 111(), 1989

Brown, Inorg. Chem. 34(), 1995

Born, Z. Phys. 1(), 1920

Kim, J. Am. Chem. Soc. 118(), 1996

Leising, Inorg. Chem. 29(), 1990

Bravo, J. Org. Chem. 61(), 1996

Bravo, Chem. Commun. (), 1996

MacFaul, J. Am. Chem. Soc. 119(), 1997

Retcher, J. Mol. Catal. A: Chem. 286(), 2008
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