Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia

Kim, Sangmin; Zhong, Hongyu; Park, Yoonsu; Loose, Florian; Chirik, Paul J.

doi:10.1021/jacs.0c03346

Title: Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia

Abstract

The catalytic hydrogenation of a metal nitride to make free ammonia using a rhodium hydride catalyst that promotes H₂ activation and hydrogen atom transfer is described. The phenylimine-substituted rhodium complex, (η⁵-C₅Me₅)Rh(^MePhI)H (^MePhI = N-methyl-1-phenylethan-1-imine) exhibited higher thermal stability compared to the previously reported (η⁵-C₅Me₅)Rh(ppy)H (ppy = 2-phenylpyridine). DFT calculations established that the two rhodium complexes have comparable Rh–H bond dissociation free energies of 51.8 kcal mol-1 for (η⁵-C₅Me₅)Rh(MePhI)H and 51.1 kcal mol^-1 for (η⁵-C₅Me₅)Rh(ppy)H. In the presence of 10 mol% of the phe-nylimine rhodium precatalyst and 4 atm of H₂ in THF, the manganese nitride, (^tBuSalen)Mn≡N underwent hydrogenation to liberate free ammonia with up to 6 total turnovers of NH₃ or 18 turnovers of H·. The phenylpyridine analogue proved inactive for ammonia synthesis under identical conditions owing to competing deleterious hydride transfer chemistry. Subsequent research showed that the use of a non-polar solvent such as benzene suppressed formation of the cationic rhodium product resulting from the hydride transfer and enabled catalytic ammonia synthesis by proton coupled electron transfer.

Authors:

^[1];

^[1]

Princeton Univ., NJ (United States). Frick Lab.

Publication Date:: Mon Apr 27 00:00:00 EDT 2020

Research Org.:: Princeton Univ., NJ (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1616530

Grant/Contract Number:: SC0006498

Resource Type:: Accepted Manuscript

Journal Name:: Journal of the American Chemical Society

Additional Journal Information:: Journal Volume: 142; Journal Issue: 20; Journal ID: ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Kim, Sangmin, Zhong, Hongyu, Park, Yoonsu, Loose, Florian, and Chirik, Paul J. Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia.  United States: N. p., 2020. 
Web.  doi:10.1021/jacs.0c03346.

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                    Kim, Sangmin, Zhong, Hongyu, Park, Yoonsu, Loose, Florian, & Chirik, Paul J. Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia.  United States.  https://doi.org/10.1021/jacs.0c03346

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                    Kim, Sangmin, Zhong, Hongyu, Park, Yoonsu, Loose, Florian, and Chirik, Paul J. Mon .  
"Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia".  United States.  https://doi.org/10.1021/jacs.0c03346.  https://www.osti.gov/servlets/purl/1616530.

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@article{osti_1616530,

  title        = {Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia},

  author       = {Kim, Sangmin and Zhong, Hongyu and Park, Yoonsu and Loose, Florian and Chirik, Paul J.},

  abstractNote = {The catalytic hydrogenation of a metal nitride to make free ammonia using a rhodium hydride catalyst that promotes H2 activation and hydrogen atom transfer is described. The phenylimine-substituted rhodium complex, (η5-C5Me5)Rh(MePhI)H (MePhI = N-methyl-1-phenylethan-1-imine) exhibited higher thermal stability compared to the previously reported (η5-C5Me5)Rh(ppy)H (ppy = 2-phenylpyridine). DFT calculations established that the two rhodium complexes have comparable Rh–H bond dissociation free energies of 51.8 kcal mol-1 for (η5-C5Me5)Rh(MePhI)H and 51.1 kcal mol-1 for (η5-C5Me5)Rh(ppy)H. In the presence of 10 mol% of the phe-nylimine rhodium precatalyst and 4 atm of H2 in THF, the manganese nitride, (tBuSalen)Mn≡N underwent hydrogenation to liberate free ammonia with up to 6 total turnovers of NH3 or 18 turnovers of H·. The phenylpyridine analogue proved inactive for ammonia synthesis under identical conditions owing to competing deleterious hydride transfer chemistry. Subsequent research showed that the use of a non-polar solvent such as benzene suppressed formation of the cationic rhodium product resulting from the hydride transfer and enabled catalytic ammonia synthesis by proton coupled electron transfer.},

  doi          = {10.1021/jacs.0c03346},

  journal      = {Journal of the American Chemical Society},

  number       = 20,

  volume       = 142,

  place        = {United States},

  year         = {Mon Apr 27 00:00:00 EDT 2020},

  month        = {Mon Apr 27 00:00:00 EDT 2020}

}

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Title: Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia

Abstract

Citation Formats

Dinitrogen Coordination Chemistry: On the Biomimetic Borderlands journal, February 2004

Dinitrogen fixation and activation after 30 years: a puzzle still unsolved journal, September 1995

Über die Bildung von Ammoniak aus den Elementen journal, October 1905

Catalytic Reduction of Dinitrogen to Ammonia at a Single Molybdenum Center journal, July 2003

Interplay between Theory and Experiment for Ammonia Synthesis Catalyzed by Transition Metal Complexes journal, April 2016

Recent Progress in Transition-Metal-Catalyzed Reduction of Molecular Dinitrogen under Ambient Reaction Conditions journal, July 2015

Recent developments in the homogeneous reduction of dinitrogen by molybdenum and iron journal, May 2013

A molybdenum complex bearing PNP-type pincer ligands leads to the catalytic reduction of dinitrogen into ammonia journal, December 2010

Unique behaviour of dinitrogen-bridged dimolybdenum complexes bearing pincer ligand towards catalytic formation of ammonia journal, April 2014

Catalytic transformation of dinitrogen into ammonia and hydrazine by iron-dinitrogen complexes bearing pincer ligand journal, July 2016

Remarkable catalytic activity of dinitrogen-bridged dimolybdenum complexes bearing NHC-based PCP-pincer ligands toward nitrogen fixation journal, April 2017

Catalytic conversion of nitrogen to ammonia by an iron model complex journal, September 2013

Ammonia Synthesis by Hydrogenolysis of Titanium–Nitrogen Bonds Using Proton Coupled Electron Transfer journal, March 2015

Catalytic Proton Coupled Electron Transfer from Metal Hydrides to Titanocene Amides, Hydrazides and Imides: Determination of Thermodynamic Parameters Relevant to Nitrogen Fixation journal, September 2016

A fresh approach to synthesizing ammonia from air and water journal, April 2019

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Dinitrogen Reduction to Ammonium at Rhenium Utilizing Light and Proton-Coupled Electron Transfer journal, November 2019

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Formation of Ammonia from an Iron Nitrido Complex journal, April 2009

Synthesis, Electrochemistry, and Reactivity of New Iridium(III) and Rhodium(III) Hydrides journal, June 2012

Kinetics and Thermodynamics of H – /H•/H + Transfer from a Rhodium(III) Hydride journal, April 2014

Pyridine(diimine) Chelate Hydrogenation in a Molybdenum Nitrido Ethylene Complex journal, April 2019

Photolytic N 2 Splitting: A Road to Sustainable NH 3 Production? journal, November 2014

Conversion of Dinitrogen into Acetonitrile under Ambient Conditions journal, March 2016

Expanding Boundaries: N 2 Cleavage and Functionalization beyond Early Transition Metals journal, June 2016

Hydrogenation of N -Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters journal, October 2019

Dicarbonylrhodium(I) Complexes of Bipyridine Ligands with Proximate H-Bonding Substituents and Their Application in Methyl Acetate Carbonylation journal, July 2011

Four-co-ordinate rhodium(I) complexes [{Rh(CO)2Cl}n(α-diimine)] (n = 1, 2) with σ,σ-N,N′ chelate or σ-N, σ-N′ bridge bonded RNC(R′)C(R″)NR ligands. Influence of the branching at Cα of R on the RhIα-diimine interaction journal, January 1981

Carbonyl rhodium(I) complexes with α-diimines ligands journal, January 1984

Transition metal-hydrogen and metal-carbon bond strengths: the keys to catalysis journal, June 1990

On the Basicity of Organic Bases in Different Media: On the Basicity of Organic Bases in Different Media journal, September 2019

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

Tuning Electronic Structure To Control Manganese Nitride Activation journal, November 2016

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Dinitrogen Coordination Chemistry: On the Biomimetic Borderlands
journal, February 2004

Dinitrogen fixation and activation after 30 years: a puzzle still unsolved
journal, September 1995

Über die Bildung von Ammoniak aus den Elementen
journal, October 1905

Catalytic Reduction of Dinitrogen to Ammonia at a Single Molybdenum Center
journal, July 2003

Interplay between Theory and Experiment for Ammonia Synthesis Catalyzed by Transition Metal Complexes
journal, April 2016

Recent Progress in Transition-Metal-Catalyzed Reduction of Molecular Dinitrogen under Ambient Reaction Conditions
journal, July 2015

Recent developments in the homogeneous reduction of dinitrogen by molybdenum and iron
journal, May 2013

A molybdenum complex bearing PNP-type pincer ligands leads to the catalytic reduction of dinitrogen into ammonia
journal, December 2010

Unique behaviour of dinitrogen-bridged dimolybdenum complexes bearing pincer ligand towards catalytic formation of ammonia
journal, April 2014

Catalytic transformation of dinitrogen into ammonia and hydrazine by iron-dinitrogen complexes bearing pincer ligand
journal, July 2016

Remarkable catalytic activity of dinitrogen-bridged dimolybdenum complexes bearing NHC-based PCP-pincer ligands toward nitrogen fixation
journal, April 2017

Catalytic conversion of nitrogen to ammonia by an iron model complex
journal, September 2013

Ammonia Synthesis by Hydrogenolysis of Titanium–Nitrogen Bonds Using Proton Coupled Electron Transfer
journal, March 2015

Catalytic Proton Coupled Electron Transfer from Metal Hydrides to Titanocene Amides, Hydrazides and Imides: Determination of Thermodynamic Parameters Relevant to Nitrogen Fixation
journal, September 2016

A fresh approach to synthesizing ammonia from air and water
journal, April 2019

Molybdenum-catalysed ammonia production with samarium diiodide and alcohols or water
journal, April 2019

Dinitrogen Reduction to Ammonium at Rhenium Utilizing Light and Proton-Coupled Electron Transfer
journal, November 2019

N–H Bond Formation in a Manganese(V) Nitride Yields Ammonia by Light-Driven Proton-Coupled Electron Transfer
journal, February 2019

Evaluation of excited state bond weakening for ammonia synthesis from a manganese nitride: stepwise proton coupled electron transfer is preferred over hydrogen atom transfer
journal, January 2019

Formation of Ammonia from an Iron Nitrido Complex
journal, April 2009

Synthesis, Electrochemistry, and Reactivity of New Iridium(III) and Rhodium(III) Hydrides
journal, June 2012

Kinetics and Thermodynamics of H ^– /H•/H ⁺ Transfer from a Rhodium(III) Hydride
journal, April 2014

Pyridine(diimine) Chelate Hydrogenation in a Molybdenum Nitrido Ethylene Complex
journal, April 2019

Photolytic N ₂ Splitting: A Road to Sustainable NH ₃ Production?
journal, November 2014

Conversion of Dinitrogen into Acetonitrile under Ambient Conditions
journal, March 2016

Expanding Boundaries: N ₂ Cleavage and Functionalization beyond Early Transition Metals
journal, June 2016

Hydrogenation of N -Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters
journal, October 2019

Dicarbonylrhodium(I) Complexes of Bipyridine Ligands with Proximate H-Bonding Substituents and Their Application in Methyl Acetate Carbonylation
journal, July 2011

Four-co-ordinate rhodium(I) complexes [{Rh(CO)2Cl}n(α-diimine)] (n = 1, 2) with σ,σ-N,N′ chelate or σ-N, σ-N′ bridge bonded RNC(R′)C(R″)NR ligands. Influence of the branching at Cα of R on the RhIα-diimine interaction
journal, January 1981

Carbonyl rhodium(I) complexes with α-diimines ligands
journal, January 1984

Transition metal-hydrogen and metal-carbon bond strengths: the keys to catalysis
journal, June 1990

On the Basicity of Organic Bases in Different Media: On the Basicity of Organic Bases in Different Media
journal, September 2019

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

Tuning Electronic Structure To Control Manganese Nitride Activation
journal, November 2016

Facile Nucleophilic Addition to Salophen Coordinated to Nitridoosmium(VI)
journal, November 2001

Construction of Pseudo-Heterochiral and Homochiral Di-μ-oxotitanium(Schiff base) Dimers and Enantioselective Epoxidation Using Aqueous Hydrogen Peroxide
journal, August 2005

An Efficient Method for the Preparation of Oxo Molybdenum Salalen Complexes and Their Unusual Use as Hydrosilylation Catalysts
journal, October 2009

Syntheses, structures and electrochemical properties of ruthenium(II/III) complexes with tetradentate Schiff base ligands
journal, February 2019