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Title: Catalytic Ammonia Oxidation to Dinitrogen by Hydrogen Atom Abstraction

Abstract

Catalysts for the oxidation of NH 3 will be critical to utilize NH 3 as a large-scale energy carrier. Molecular complexes have not been shown to catalyze the oxidation of NH 3 to N 2. We report Ru- catalyzed oxidation of ammonia to dinitrogen under ambient conditions using the molecular complex [Cp*Ru(P tBu 2N Ph 2)( 15NH 3)][BAr F 4]. Mediating the cleavage of six N-H bonds and the formation of an N≡N bond was achieved by coupling H + and e - transfers as net hydrogen atom abstraction steps using the 2,4,6-tri- tert-butylphenoxyl radical ( tBu 3ArO•) as the H atom acceptor. Employing an excess of tBu 3ArO• under 1 atm of NH 3 gas at 23 °C resulted in up to six turnovers. As a result, nitrogen isotopic ( 15N) labeling studies provide mechanistic insights to confirm the N≡N bond forming step in the catalytic cycle.

Authors:
 [1]; ORCiD logo [2];  [1];  [1]; ORCiD logo [1]; ORCiD logo [3]
  1. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
  2. Washington State Univ., Pullman, WA (United States)
  3. Montana State Univ., Bozeman, MT (United States)
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1572935
Alternate Identifier(s):
OSTI ID: 1525550
Report Number(s):
[PNNL-SA-137210]
[Journal ID: ISSN 1433-7851; ANIE]
Grant/Contract Number:  
[AC05-76RL01830]
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
[Journal Name: Angewandte Chemie (International Edition); Journal Volume: 58; Journal Issue: 34]; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; ammonia oxidation; dinitrogen; homogeneous catalysis; radical reactions; ruthenium

Citation Formats

Bhattacharya, Papri, Heiden, Zachariah M., Chambers, Geoffrey M., Johnson, Samantha I., Bullock, R. Morris, and Mock, Michael T. Catalytic Ammonia Oxidation to Dinitrogen by Hydrogen Atom Abstraction. United States: N. p., 2019. Web. doi:10.1002/anie.201903221.
Bhattacharya, Papri, Heiden, Zachariah M., Chambers, Geoffrey M., Johnson, Samantha I., Bullock, R. Morris, & Mock, Michael T. Catalytic Ammonia Oxidation to Dinitrogen by Hydrogen Atom Abstraction. United States. doi:10.1002/anie.201903221.
Bhattacharya, Papri, Heiden, Zachariah M., Chambers, Geoffrey M., Johnson, Samantha I., Bullock, R. Morris, and Mock, Michael T. Tue . "Catalytic Ammonia Oxidation to Dinitrogen by Hydrogen Atom Abstraction". United States. doi:10.1002/anie.201903221.
@article{osti_1572935,
title = {Catalytic Ammonia Oxidation to Dinitrogen by Hydrogen Atom Abstraction},
author = {Bhattacharya, Papri and Heiden, Zachariah M. and Chambers, Geoffrey M. and Johnson, Samantha I. and Bullock, R. Morris and Mock, Michael T.},
abstractNote = {Catalysts for the oxidation of NH3 will be critical to utilize NH3 as a large-scale energy carrier. Molecular complexes have not been shown to catalyze the oxidation of NH3 to N2. We report Ru- catalyzed oxidation of ammonia to dinitrogen under ambient conditions using the molecular complex [Cp*Ru(PtBu2NPh2)(15NH3)][BArF4]. Mediating the cleavage of six N-H bonds and the formation of an N≡N bond was achieved by coupling H+ and e- transfers as net hydrogen atom abstraction steps using the 2,4,6-tri-tert-butylphenoxyl radical (tBu3ArO•) as the H atom acceptor. Employing an excess of tBu3ArO• under 1 atm of NH3 gas at 23 °C resulted in up to six turnovers. As a result, nitrogen isotopic (15N) labeling studies provide mechanistic insights to confirm the N≡N bond forming step in the catalytic cycle.},
doi = {10.1002/anie.201903221},
journal = {Angewandte Chemie (International Edition)},
number = [34],
volume = [58],
place = {United States},
year = {2019},
month = {5}
}

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    Works referencing / citing this record:

    Synthesis and Ligand Modification Chemistry of a Molybdenum Dinitrogen Complex: Redox and Chemical Activity of a Bis(imino)pyridine Ligand
    journal, October 2014

    • Margulieux, Grant W.; Turner, Zoë R.; Chirik, Paul J.
    • Angewandte Chemie, Vol. 126, Issue 51
    • DOI: 10.1002/ange.201408725

    Interconversion of Molybdenum Imido and Amido Complexes by Proton-Coupled Electron Transfer
    journal, January 2018


    Synthesis and Ligand Modification Chemistry of a Molybdenum Dinitrogen Complex: Redox and Chemical Activity of a Bis(imino)pyridine Ligand
    journal, October 2014

    • Margulieux, Grant W.; Turner, Zoë R.; Chirik, Paul J.
    • Angewandte Chemie International Edition, Vol. 53, Issue 51
    • DOI: 10.1002/anie.201408725

    Interconversion of Molybdenum Imido and Amido Complexes by Proton-Coupled Electron Transfer
    journal, January 2018

    • Bezdek, Máté J.; Chirik, Paul J.
    • Angewandte Chemie International Edition, Vol. 57, Issue 8
    • DOI: 10.1002/anie.201708406

    Oxydation d'Amines Aromatiques Primaires en Présence du Radical Tritertiobutyl-2,4,6 Phénoxyle
    journal, January 1987

    • Hedoyatullah, Mir; Thevenet, Francis
    • Bulletin des Sociétés Chimiques Belges, Vol. 96, Issue 4
    • DOI: 10.1002/bscb.19870960407

    Towards Catalytic Ammonia Oxidation to Dinitrogen: A Synthetic Cycle by Using a Simple Manganese Complex
    journal, August 2017

    • Keener, Megan; Peterson, Madeline; Hernández Sánchez, Raúl
    • Chemistry - A European Journal, Vol. 23, Issue 48
    • DOI: 10.1002/chem.201703153

    NBO 6.0 : Natural bond orbital analysis program
    journal, March 2013

    • Glendening, Eric D.; Landis, Clark R.; Weinhold, Frank
    • Journal of Computational Chemistry, Vol. 34, Issue 16
    • DOI: 10.1002/jcc.23266

    Ammonia-fed fuel cells: a comprehensive review
    journal, July 2016

    • Afif, Ahmed; Radenahmad, Nikdalila; Cheok, Quentin
    • Renewable and Sustainable Energy Reviews, Vol. 60
    • DOI: 10.1016/j.rser.2016.01.120

    Homolytic N–H Activation of Ammonia: Hydrogen Transfer of Parent Iridium Ammine, Amide, Imide, and Nitride Species
    journal, July 2015


    Catalytic Acceptorless Dehydrogenation of Amines with Ru(P R 2 N R′ 2 ) and Ru(dppp) Complexes
    journal, April 2017


    As Precious as Platinum: Iron Nitride for Electrocatalytic Oxidation of Liquid Ammonia
    journal, May 2017

    • Little, Daniel J.; Edwards, Dillon O.; Smith, Milton R.
    • ACS Applied Materials & Interfaces, Vol. 9, Issue 19
    • DOI: 10.1021/acsami.7b02639

    Reactivity of Nitrido Complexes of Ruthenium(VI), Osmium(VI), and Manganese(V) Bearing Schiff Base and Simple Anionic Ligands
    journal, September 2013

    • Man, Wai-Lun; Lam, William W. Y.; Lau, Tai-Chu
    • Accounts of Chemical Research, Vol. 47, Issue 2
    • DOI: 10.1021/ar400147y

    Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications
    journal, December 2010

    • Warren, Jeffrey J.; Tronic, Tristan A.; Mayer, James M.
    • Chemical Reviews, Vol. 110, Issue 12
    • DOI: 10.1021/cr100085k

    Mechanism of Nitrogen Fixation by Nitrogenase: The Next Stage
    journal, January 2014

    • Hoffman, Brian M.; Lukoyanov, Dmitriy; Yang, Zhi-Yong
    • Chemical Reviews, Vol. 114, Issue 8
    • DOI: 10.1021/cr400641x

    Nitrogen Cycle Electrocatalysis
    journal, June 2009

    • Rosca, Victor; Duca, Matteo; de Groot, Matheus T.
    • Chemical Reviews, Vol. 109, Issue 6
    • DOI: 10.1021/cr8003696

    Substitution-induced nitrogen-nitrogen coupling for nitride coordinated to osmium(VI)
    journal, November 1991

    • Ware, David C.; Taube, Henry.
    • Inorganic Chemistry, Vol. 30, Issue 24
    • DOI: 10.1021/ic00024a029

    The Remarkable Reactivity of High Oxidation State Ruthenium and Osmium Polypyridyl Complexes
    journal, December 2003

    • Meyer, Thomas J.; Huynh, My Hang V.
    • Inorganic Chemistry, Vol. 42, Issue 25
    • DOI: 10.1021/ic020731v

    Dinitrogen Formation by Oxidative Intramolecular N---N Coupling in cis,cis- [(bpy) 2 (NH 3 )RuORu(NH 3 )(bpy) 2 ] 4+
    journal, March 2003

    • Ishitani, Osamu; Ando, Emiko; Meyer, Thomas J.
    • Inorganic Chemistry, Vol. 42, Issue 5
    • DOI: 10.1021/ic026096a

    Side-on Bound Diazene and Hydrazine Complexes of Ruthenium
    journal, July 2010

    • Field, Leslie D.; Li, Hsiu L.; Dalgarno, Scott J.
    • Inorganic Chemistry, Vol. 49, Issue 13
    • DOI: 10.1021/ic100821u

    Synthesis, Protonation, and Reduction of Ruthenium–Peroxo Complexes with Pendent Nitrogen Bases
    journal, October 2012

    • Tronic, Tristan A.; Kaminsky, Werner; Coggins, Michael K.
    • Inorganic Chemistry, Vol. 51, Issue 20
    • DOI: 10.1021/ic3013987

    Base-Induced Dehydrogenation of Ruthenium Hydrazine Complexes
    journal, January 2013

    • Field, Leslie D.; Li, Hsiu L.; Dalgarno, Scott J.
    • Inorganic Chemistry, Vol. 52, Issue 3
    • DOI: 10.1021/ic302449n

    Oxidation of pentaamminecarbonylosmium(2+) to .mu.-dinitrogen-bis(cis-tetraamminecarbonylosmium)(4+)
    journal, August 1979


    Reactions of ammonia with porous glass surfaces
    journal, May 1967

    • Low, Manfred J. D.; Ramasubramanian, Natesan; Rao, V. V. Subba
    • The Journal of Physical Chemistry, Vol. 71, Issue 6
    • DOI: 10.1021/j100865a028

    Toward a dinitrogen electroreduction catalyst: characterization of a bis-ammine, a .mu.2-hydrazine, a .mu.2-diazene, and a remarkably stable .mu.2-dinitrogen complex of a ruthenium cofacial diporphyrin
    journal, March 1991

    • Collman, James P.; Hutchison, James E.; Lopez, Michel Angel
    • Journal of the American Chemical Society, Vol. 113, Issue 7
    • DOI: 10.1021/ja00007a088

    Reversible interconversion between a nitrido complex of osmium(VI) and an ammine complex of osmium(II)
    journal, July 1990

    • Pipes, David W.; Bakir, Mohammed; Vitols, S. E.
    • Journal of the American Chemical Society, Vol. 112, Issue 14
    • DOI: 10.1021/ja00170a014

    Multiple Mixed-Valence Behavior in trans , trans -[(tpy)(Cl) 2 Os III (μ-1,3-N 3 )Os III (Cl) 2 (tpy)] + . An Azido Bridge from the Reaction between trans -[Os VI (tpy)(Cl) 2 (N)] + and NH 3
    journal, March 2003

    • Huynh, My Hang V.; Meyer, Thomas J.; Labouriau, Andrea
    • Journal of the American Chemical Society, Vol. 125, Issue 10
    • DOI: 10.1021/ja021324l

    Highly Electrophilic (Salen)ruthenium(VI) Nitrido Complexes
    journal, January 2004

    • Man, Wai-Lun; Tang, Tsz-Man; Wong, Tsz-Wing
    • Journal of the American Chemical Society, Vol. 126, Issue 2
    • DOI: 10.1021/ja037899f

    Iron Diazoalkane Chemistry:  N−N Bond Hydrogenation and Intramolecular C−H Activation
    journal, June 2007

    • Bart, Suzanne C.; Bowman, Amanda C.; Lobkovsky, Emil
    • Journal of the American Chemical Society, Vol. 129, Issue 23
    • DOI: 10.1021/ja070056u

    Addition of Ammonia, Water, and Dihydrogen Across a Single Pd−Pd Bond
    journal, August 2007

    • Fafard, Claudia M.; Adhikari, Debashis; Foxman, Bruce M.
    • Journal of the American Chemical Society, Vol. 129, Issue 34
    • DOI: 10.1021/ja0731571

    Activation of Water, Ammonia, and Other Small Molecules by PC carbene P Nickel Pincer Complexes
    journal, July 2013

    • Gutsulyak, Dmitry V.; Piers, Warren E.; Borau-Garcia, Javier
    • Journal of the American Chemical Society, Vol. 135, Issue 32
    • DOI: 10.1021/ja406742n

    Hydrogen Production from Ammonia Using Sodium Amide
    journal, June 2014

    • David, William I. F.; Makepeace, Joshua W.; Callear, Samantha K.
    • Journal of the American Chemical Society, Vol. 136, Issue 38
    • DOI: 10.1021/ja5042836

    Ammonia Oxidation by Abstraction of Three Hydrogen Atoms from a Mo–NH 3 Complex
    journal, February 2017

    • Bhattacharya, Papri; Heiden, Zachariah M.; Wiedner, Eric S.
    • Journal of the American Chemical Society, Vol. 139, Issue 8
    • DOI: 10.1021/jacs.7b00002

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