Literature DB >> 19130517

A two-state reactivity model explains unusual kinetic isotope effect patterns in C-H bond cleavage by nonheme oxoiron(IV) complexes.

Eric J Klinker1, Sason Shaik, Hajime Hirao, Lawrence Que.   

Abstract

It's in the bond: The cleavage of C-H bonds by two related oxoiron(IV) complexes shows a range of kinetic isotope effect (KIE) values that exhibit an unusual dependence on the C-H bond strength. Large nonclassical KIEs are observed for bond strengths below 93 kcal mol(-1), while semiclassical values are found above this value (see graph, DHA = 9,10-dihydroanthracene). This nonintuitive behavior can be rationalized by invoking a two-state reactivity model.

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Year:  2009        PMID： 19130517      PMCID： PMC2832581          DOI： 10.1002/anie.200804029

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  20 in total

1.  Two-state reactivity as a new concept in organometallic chemistry.

Authors:  D Schröder; S Shaik; H Schwarz
Journal:  Acc Chem Res       Date:  2000-03       Impact factor: 22.384

2.  Nonheme FeIVO complexes that can oxidize the C-H bonds of cyclohexane at room temperature.

Authors:  József Kaizer; Eric J Klinker; Na Young Oh; Jan-Uwe Rohde; Woon Ju Song; Audria Stubna; Jinheung Kim; Eckard Münck; Wonwoo Nam; Lawrence Que
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419

3.  Two-state reactivity in alkane hydroxylation by non-heme iron-oxo complexes.

Authors:  Hajime Hirao; Devesh Kumar; Lawrence Que; Sason Shaik
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

Review 4.  High-valent nonheme iron-oxo species in biomimetic oxidations.

Authors:  Xiaopeng Shan; Lawrence Que
Journal:  J Inorg Biochem       Date:  2006-03-13       Impact factor: 4.155

Review 5.  The road to non-heme oxoferryls and beyond.

Authors:  Lawrence Que
Journal:  Acc Chem Res       Date:  2007-06-27       Impact factor: 22.384

6.  Experiment and theory reveal the fundamental difference between two-state and single-state reactivity patterns in nonheme Fe(IV)=O versus Ru(IV)=O oxidants.

Authors:  Sunder N Dhuri; Mi Sook Seo; Yong-Min Lee; Hajime Hirao; Yong Wang; Wonwoo Nam; Sason Shaik
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 7.  Reactivity of high-valent iron-oxo species in enzymes and synthetic reagents: a tale of many states.

Authors:  Sason Shaik; Hajime Hirao; Devesh Kumar
Journal:  Acc Chem Res       Date:  2007-05-09       Impact factor: 22.384

8.  Evidence for hydrogen abstraction from C1 of taurine by the high-spin Fe(IV) intermediate detected during oxygen activation by taurine:alpha-ketoglutarate dioxygenase (TauD).

Authors:  John C Price; Eric W Barr; Timothy E Glass; Carsten Krebs; J Martin Bollinger
Journal:  J Am Chem Soc       Date:  2003-10-29       Impact factor: 15.419

9.  A valence bond modeling of trends in hydrogen abstraction barriers and transition states of hydroxylation reactions catalyzed by cytochrome P450 enzymes.

Authors:  Sason Shaik; Devesh Kumar; Sam P de Visser
Journal:  J Am Chem Soc       Date:  2008-07-11       Impact factor: 15.419

10.  The first direct characterization of a high-valent iron intermediate in the reaction of an alpha-ketoglutarate-dependent dioxygenase: a high-spin FeIV complex in taurine/alpha-ketoglutarate dioxygenase (TauD) from Escherichia coli.

Authors:  John C Price; Eric W Barr; Bhramara Tirupati; J Martin Bollinger; Carsten Krebs
Journal:  Biochemistry       Date:  2003-06-24       Impact factor: 3.162
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  23 in total

1.  Redox potential and C-H bond cleaving properties of a nonheme Fe(IV)=O complex in aqueous solution.

Authors:  Dong Wang; Mo Zhang; Philippe Bühlmann; Lawrence Que
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

2.  Modeling the cis-oxo-labile binding site motif of non-heme iron oxygenases: water exchange and oxidation reactivity of a non-heme iron(IV)-oxo compound bearing a tripodal tetradentate ligand.

Authors:  Anna Company; Irene Prat; Jonathan R Frisch; Ruben Mas-Ballesté; Mireia Güell; Gergely Juhász; Xavi Ribas; Eckard Münck; Josep M Luis; Lawrence Que; Miquel Costas
Journal:  Chemistry       Date:  2011-01-05       Impact factor: 5.236

3.  Tuning the Reactivity of Terminal Nickel(III)-Oxygen Adducts for C-H Bond Activation.

Authors:  Paolo Pirovano; Erik R Farquhar; Marcel Swart; Aidan R McDonald
Journal:  J Am Chem Soc       Date:  2016-10-24       Impact factor: 15.419

4.  Substrate placement influences reactivity in non-heme Fe(II) halogenases and hydroxylases.

Authors:  Heather J Kulik; Catherine L Drennan
Journal:  J Biol Chem       Date:  2013-02-28       Impact factor: 5.157

5.  Structural Characterization of a Series of N5-Ligated MnIV -Oxo Species.

Authors:  Allyssa A Massie; Melissa C Denler; Reena Singh; Arup Sinha; Ebbe Nordlander; Timothy A Jackson
Journal:  Chemistry       Date:  2019-12-20       Impact factor: 5.236

6.  Detection and kinetic characterization of a highly reactive heme-thiolate peroxygenase compound I.

Authors:  Xiaoshi Wang; Sebastian Peter; Matthias Kinne; Martin Hofrichter; John T Groves
Journal:  J Am Chem Soc       Date:  2012-07-26       Impact factor: 15.419

7.  Nonheme Oxoiron(IV) Complexes of Pentadentate N5 Ligands: Spectroscopy, Electrochemistry, and Oxidative Reactivity.

Authors:  Dong Wang; Kallol Ray; Michael J Collins; Erik R Farquhar; Jonathan R Frisch; Laura Gómez; Timothy A Jackson; Marion Kerscher; Arkadius Waleska; Peter Comba; Miquel Costas; Lawrence Que
Journal:  Chem Sci       Date:  2013-01       Impact factor: 9.825

8.  Parallel and competitive pathways for substrate desaturation, hydroxylation, and radical rearrangement by the non-heme diiron hydroxylase AlkB.

Authors:  Harriet L R Cooper; Girish Mishra; Xiongyi Huang; Marilla Pender-Cudlip; Rachel N Austin; John Shanklin; John T Groves
Journal:  J Am Chem Soc       Date:  2012-12-10       Impact factor: 15.419

9.  Catalytic hydrogenation activity and electronic structure determination of bis(arylimidazol-2-ylidene)pyridine cobalt alkyl and hydride complexes.

Authors:  Renyuan Pony Yu; Jonathan M Darmon; Carsten Milsmann; Grant W Margulieux; S Chantal E Stieber; Serena DeBeer; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2013-08-22       Impact factor: 15.419

10.  Reactivities of Fe(IV) complexes with oxo, hydroxo, and alkylperoxo ligands: an experimental and computational study.

Authors:  Adam T Fiedler; Lawrence Que
Journal:  Inorg Chem       Date:  2009-12-07       Impact factor: 5.165
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