Acceleration of CO 2 insertion into metal hydrides: ligand, Lewis acid, and solvent effects on reaction kinetics

Heimann, Jessica E.; Bernskoetter, Wesley H.; Hazari, Nilay; Mayer, James M.

doi:10.1039/C8SC02535E

Acceleration of CO ₂ insertion into metal hydrides: ligand, Lewis acid, and solvent effects on reaction kinetics

Journal Article · Sun Dec 31 23:00:00 EST 2017 · Chemical Science

DOI:https://doi.org/10.1039/C8SC02535E· OSTI ID:1460464

Heimann, Jessica E. ^[1]; ^[2]; ^[1]; ^[1]

Department of Chemistry, Yale University, New Haven, USA
Department of Chemistry, University of Missouri, Columbia, USA

Kinetic studies of CO ₂ insertion into transition metal hydrides provide evidence about the nature of the rate-determining transition state.

View Journal Article

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0018222; SC0001059

OSTI ID:: 1460464

Alternate ID(s):: OSTI ID: 1505499

Journal Information:: Chemical Science, Journal Name: Chemical Science Journal Issue: 32 Vol. 9; ISSN 2041-6520; ISSN CSHCBM

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (59)

Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? Cokoja, Mirza; Bruckmeier, Christian; Rieger, Bernhard Angewandte Chemie International Edition, Vol. 50, Issue 37 https://doi.org/10.1002/anie.201102010	journal	August 2011
Low-Pressure Hydrogenation of Carbon Dioxide Catalyzed by an Iron Pincer Complex Exhibiting Noble Metal Activity Langer, Robert; Diskin-Posner, Yael; Leitus, Gregory Angewandte Chemie International Edition, Vol. 50, Issue 42 https://doi.org/10.1002/anie.201104542	journal	September 2011
Selective Catalytic Synthesis Using the Combination of Carbon Dioxide and Hydrogen: Catalytic Chess at the Interface of Energy and Chemistry Klankermayer, Jürgen; Wesselbaum, Sebastian; Beydoun, Kassem Angewandte Chemie International Edition, Vol. 55, Issue 26 https://doi.org/10.1002/anie.201507458	journal	May 2016
A Stable Manganese Pincer Catalyst for the Selective Dehydrogenation of Methanol Andérez-Fernández, María; Vogt, Lydia K.; Fischer, Steffen Angewandte Chemie International Edition, Vol. 56, Issue 2 https://doi.org/10.1002/anie.201610182	journal	December 2016
Efficient Hydrogen Liberation from Formic Acid Catalyzed by a Well-Defined Iron Pincer Complex under Mild Conditions Zell, Thomas; Butschke, Burkhard; Ben-David, Yehoshoa Chemistry - A European Journal, Vol. 19, Issue 25 https://doi.org/10.1002/chem.201301383	journal	May 2013
Chemical Technologies for Exploiting and Recycling Carbon Dioxide into the Value Chain Peters, Martina; Köhler, Burkhard; Kuckshinrichs, Wilhelm ChemSusChem, Vol. 4, Issue 9 https://doi.org/10.1002/cssc.201000447	journal	August 2011
A Computational Investigation of the Insertion of Carbon Dioxide into Four- and Five-Coordinate Iridium Hydrides Bernskoetter, Wesley H.; Hazari, Nilay European Journal of Inorganic Chemistry, Vol. 2013, Issue 22-23 https://doi.org/10.1002/ejic.201300170	journal	May 2013
The acceptor number ? A quantitative empirical parameter for the electrophilic properties of solvents Mayer, Ulrich; Gutmann, Viktor; Gerger, Wolfgang Monatshefte f�r Chemie, Vol. 106, Issue 6 https://doi.org/10.1007/BF00913599	journal	January 1975
Synthesis and properties of [Ru(tpy)(4,4′-X2bpy)H]+ (tpy=2,2′:6′,2″-terpyridine, bpy=2,2′-bipyridine, X=H and MeO), and their reactions with CO2 Konno, Hideo; Kobayashi, Atsuo; Sakamoto, Kazuhiko Inorganica Chimica Acta, Vol. 299, Issue 2 https://doi.org/10.1016/S0020-1693(99)00488-0	journal	March 2000
Reversible Hydrogenation of Carbon Dioxide to Formic Acid and Methanol: Lewis Acid Enhancement of Base Metal Catalysts Bernskoetter, Wesley H.; Hazari, Nilay Accounts of Chemical Research, Vol. 50, Issue 4 https://doi.org/10.1021/acs.accounts.7b00039	journal	February 2017
CO ₂ Hydrogenation to Formate and Methanol as an Alternative to Photo- and Electrochemical CO ₂ Reduction Wang, Wan-Hui; Himeda, Yuichiro; Muckerman, James T. Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00197	journal	August 2015
Homogeneous Catalysis for Sustainable Hydrogen Storage in Formic Acid and Alcohols Sordakis, Katerina; Tang, Conghui; Vogt, Lydia K. Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00182	journal	October 2017
Effective Pincer Cobalt Precatalysts for Lewis Acid Assisted CO ₂ Hydrogenation Spentzos, Ariana Z.; Barnes, Charles L.; Bernskoetter, Wesley H. Inorganic Chemistry, Vol. 55, Issue 16 https://doi.org/10.1021/acs.inorgchem.6b01454	journal	July 2016
Carbon Dioxide Insertion into Group 9 and 10 Metal–Element σ Bonds Hazari, Nilay; Heimann, Jessica E. Inorganic Chemistry, Vol. 56, Issue 22 https://doi.org/10.1021/acs.inorgchem.7b02315	journal	November 2017
SambVca 2. A Web Tool for Analyzing Catalytic Pockets with Topographic Steric Maps Falivene, Laura; Credendino, Raffaele; Poater, Albert Organometallics, Vol. 35, Issue 13 https://doi.org/10.1021/acs.organomet.6b00371	journal	June 2016
Reactivity of (Pyridine-Diimine)Fe Alkyl Complexes with Carbon Dioxide Lau, Ka-Cheong; Jordan, Richard F. Organometallics, Vol. 35, Issue 21 https://doi.org/10.1021/acs.organomet.6b00470	journal	August 2016
Using CS ₂ to Probe the Mechanistic Details of Decarboxylation of Bis(phosphinite)-Ligated Nickel Pincer Formate Complexes Ma, Qiang-Qiang; Liu, Ting; Adhikary, Anubendu Organometallics, Vol. 35, Issue 24 https://doi.org/10.1021/acs.organomet.6b00759	journal	December 2016
Iridium and Ruthenium Complexes of N -Heterocyclic Carbene- and Pyridinol-Derived Chelates as Catalysts for Aqueous Carbon Dioxide Hydrogenation and Formic Acid Dehydrogenation: The Role of the Alkali Metal Siek, Sopheavy; Burks, Dalton B.; Gerlach, Deidra L. Organometallics, Vol. 36, Issue 6 https://doi.org/10.1021/acs.organomet.6b00806	journal	March 2017
Weakly Coordinating yet Ion Paired: Anion Effects on an Internal Rearrangement Aldrich, Kelly E.; Billow, Brennan S.; Holmes, Daniel Organometallics, Vol. 36, Issue 7 https://doi.org/10.1021/acs.organomet.6b00839	journal	January 2017
Base-Free Methanol Dehydrogenation Using a Pincer-Supported Iron Compound and Lewis Acid Co-catalyst Bielinski, Elizabeth A.; Förster, Moritz; Zhang, Yuanyuan ACS Catalysis, Vol. 5, Issue 4 https://doi.org/10.1021/acscatal.5b00137	journal	March 2015
Mechanistic Studies on the Selective Reduction of CO ₂ to the Aldehyde Level by a Bis(phosphino)boryl (PBP)-Supported Nickel Complex Ríos, Pablo; Rodríguez, Amor; López-Serrano, Joaquín ACS Catalysis, Vol. 6, Issue 9 https://doi.org/10.1021/acscatal.6b01715	journal	August 2016
Ion Pairing Marcus, Yizhak; Hefter, Glenn Chemical Reviews, Vol. 106, Issue 11 https://doi.org/10.1021/cr040087x	journal	November 2006
Frontiers, Opportunities, and Challenges in Biochemical and Chemical Catalysis of CO ₂ Fixation Appel, Aaron M.; Bercaw, John E.; Bocarsly, Andrew B. Chemical Reviews, Vol. 113, Issue 8 https://doi.org/10.1021/cr300463y	journal	June 2013
Fast Carbon Dioxide Fixation by 2,6-Pyridinedicarboxamidato-nickel(II)-hydroxide Complexes: Influence of Changes in Reactive Site Environment on Reaction Rates Huang, Deguang; Makhlynets, Olga V.; Tan, Lay Ling Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic200942u	journal	October 2011
Kinetic Aspects for the Reduction of CO ₂ and CS ₂ with Mixed-Ligand Ruthenium(II) Hydride Complexes Containing Phosphine and Bipyridine Huang, Jing; Chen, Jinzhu; Gao, Hui Inorganic Chemistry, Vol. 53, Issue 18 https://doi.org/10.1021/ic500866d	journal	August 2014
Synthesis, Characterization, and Reactivity of Nickel Hydride Complexes Containing 2,6-C ₆ H ₃ (CH ₂ PR ₂ ) ₂ (R = t Bu, c Hex, and i Pr) Pincer Ligands Boro, Brian J.; Duesler, Eileen N.; Goldberg, Karen I. Inorganic Chemistry, Vol. 48, Issue 12 https://doi.org/10.1021/ic8020194	journal	June 2009
Dissociation of lithium and sodium salts in ethereal solvents Nicholls, Derek; Sutphen, C.; Szwarc, Michael The Journal of Physical Chemistry, Vol. 72, Issue 3 https://doi.org/10.1021/j100849a041	journal	March 1968
Studies of Ions and Ion Pairs in Tetrahydrofuran Solution. Alkali Metal Salts of Tetraphenylboride Bhattacharyya, D. N.; Lee, C. L.; Smid, J. The Journal of Physical Chemistry, Vol. 69, Issue 2 https://doi.org/10.1021/j100886a042	journal	February 1965
Cation-anion interaction in the [Na-kryptofix-221][W(CO)5O2CH] derivative and its relevance in carbon dioxide reduction processes Darensbourg, Donald J.; Pala, Magdalena Journal of the American Chemical Society, Vol. 107, Issue 20 https://doi.org/10.1021/ja00306a014	journal	October 1985
Reduction of carbon dioxide and carbonyl sulfide by anionic Group VIB metal hydrides and alkyls. Carbon-hydrogen and carbon-carbon bond formation processes and the structure of [PNP][Cr(CO)5SC(O)H] Darensbourg, Donald J.; Rokicki, Andrzej Journal of the American Chemical Society, Vol. 104, Issue 1 https://doi.org/10.1021/ja00365a089	journal	January 1982
Activation of coordinated carbon monoxide toward alkyl and aryl migration (carbon monoxide insertion) by molecular Lewis acids and x-ray structure of the reactive intermediate Butts, Susan Beda; Strauss, Steven H.; Holt, Elizabeth M. Journal of the American Chemical Society, Vol. 102, Issue 15 https://doi.org/10.1021/ja00535a048	journal	July 1980
Combined Computational and Experimental Study of Substituent Effects on the Thermodynamics of H ₂ , CO, Arene, and Alkane Addition to Iridium Krogh-Jespersen, Karsten; Czerw, Margaret; Zhu, Keming Journal of the American Chemical Society, Vol. 124, Issue 36 https://doi.org/10.1021/ja010547t	journal	September 2002
Rapid Transfer of Hydride Ion from a Ruthenium Complex to C ₁ Species in Water Creutz, Carol; Chou, Mei H. Journal of the American Chemical Society, Vol. 129, Issue 33 https://doi.org/10.1021/ja074158w	journal	August 2007
Secondary Coordination Sphere Interactions Facilitate the Insertion Step in an Iridium(III) CO ₂ Reduction Catalyst Schmeier, Timothy J.; Dobereiner, Graham E.; Crabtree, Robert H. Journal of the American Chemical Society, Vol. 133, Issue 24 https://doi.org/10.1021/ja2035514	journal	June 2011
Cascade Catalysis for the Homogeneous Hydrogenation of CO ₂ to Methanol Huff, Chelsea A.; Sanford, Melanie S. Journal of the American Chemical Society, Vol. 133, Issue 45 https://doi.org/10.1021/ja208760j	journal	November 2011
Selective Electrocatalytic Reduction of CO ₂ to Formate by Water-Stable Iridium Dihydride Pincer Complexes Kang, Peng; Cheng, Chen; Chen, Zuofeng Journal of the American Chemical Society, Vol. 134, Issue 12 https://doi.org/10.1021/ja300543s	journal	March 2012
Well-Defined Iron Catalyst for Improved Hydrogenation of Carbon Dioxide and Bicarbonate Ziebart, Carolin; Federsel, Christopher; Anbarasan, Pazhamalai Journal of the American Chemical Society, Vol. 134, Issue 51 https://doi.org/10.1021/ja307924a	journal	December 2012
A Cobalt-Based Catalyst for the Hydrogenation of CO ₂ under Ambient Conditions Jeletic, Matthew S.; Mock, Michael T.; Appel, Aaron M. Journal of the American Chemical Society, Vol. 135, Issue 31 https://doi.org/10.1021/ja406601v	journal	July 2013
Lewis Acid-Assisted Formic Acid Dehydrogenation Using a Pincer-Supported Iron Catalyst Bielinski, Elizabeth A.; Lagaditis, Paraskevi O.; Zhang, Yuanyuan Journal of the American Chemical Society, Vol. 136, Issue 29 https://doi.org/10.1021/ja505241x	journal	July 2014
Tandem Amine and Ruthenium-Catalyzed Hydrogenation of CO ₂ to Methanol Rezayee, Nomaan M.; Huff, Chelsea A.; Sanford, Melanie S. Journal of the American Chemical Society, Vol. 137, Issue 3 https://doi.org/10.1021/ja511329m	journal	January 2015
Catalytic Hydrogenation of Carbon Dioxide Using Ir(III)−Pincer Complexes Tanaka, Ryo; Yamashita, Makoto; Nozaki, Kyoko Journal of the American Chemical Society, Vol. 131, Issue 40 https://doi.org/10.1021/ja903574e	journal	October 2009
Incorporation of Pendant Bases into Rh(diphosphine) ₂ Complexes: Synthesis, Thermodynamic Studies, And Catalytic CO ₂ Hydrogenation Activity of [Rh(P ₂ N ₂ ) ₂ ] ⁺ Complexes Lilio, Alyssia M.; Reineke, Mark H.; Moore, Curtis E. Journal of the American Chemical Society, Vol. 137, Issue 25 https://doi.org/10.1021/jacs.5b04291	journal	June 2015
Unravelling the Mechanism of Basic Aqueous Methanol Dehydrogenation Catalyzed by Ru–PNP Pincer Complexes Alberico, Elisabetta; Lennox, Alastair J. J.; Vogt, Lydia K. Journal of the American Chemical Society, Vol. 138, Issue 45 https://doi.org/10.1021/jacs.6b05692	journal	November 2016
Kinetics and mechanism of carbon dioxide insertion into a metal-hydride bond. A large solvent effect and an inverse kinetic isotope effect Sullivan, B. Patrick.; Meyer, Thomas J. Organometallics, Vol. 5, Issue 7 https://doi.org/10.1021/om00138a035	journal	July 1986
A Family of Active Iridium Catalysts for Transfer Hydrogenation of Ketones Clarke, Zaheer E.; Maragh, Paul T.; Dasgupta, Tara P. Organometallics, Vol. 25, Issue 17 https://doi.org/10.1021/om060049z	journal	August 2006
Synthesis and Reactivity of Nickel and Palladium Fluoride Complexes with PCP Pincer Ligands. NMR-Based Assessment of Electron-Donating Properties of Fluoride and Other Monoanionic Ligands Martı́nez-Prieto, Luis Miguel; Melero, Cristóbal; del Rı́o, Diego Organometallics, Vol. 31, Issue 4 https://doi.org/10.1021/om2009793	journal	November 2011
Experimental and Computational Studies of the Reaction of Carbon Dioxide with Pincer-Supported Nickel and Palladium Hydrides Suh, Hee-Won; Schmeier, Timothy J.; Hazari, Nilay Organometallics, Vol. 31, Issue 23 https://doi.org/10.1021/om3008597	journal	November 2012
Comparative Reactivity of Zr– and Pd–Alkyl Complexes with Carbon Dioxide Lau, Ka-Cheong; Petro, Benjamin J.; Bontemps, Sébastien Organometallics, Vol. 32, Issue 23 https://doi.org/10.1021/om401082k	journal	November 2013
Reversible hydrogen storage using CO₂ and a proton-switchable iridium catalyst in aqueous media under mild temperatures and pressures Hull, Jonathan F.; Himeda, Yuichiro; Wang, Wan-Hui Nature Chemistry, Vol. 4, Issue 5, p. 383-388 https://doi.org/10.1038/nchem.1295	journal	March 2012
A prolific catalyst for dehydrogenation of neat formic acid Celaje, Jeff Joseph A.; Lu, Zhiyao; Kedzie, Elyse A. Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms11308	journal	April 2016
Exploring the reactions of CO ₂ with PCP supported nickel complexes Schmeier, Timothy J.; Hazari, Nilay; Incarvito, Christopher D. Chem. Commun., Vol. 47, Issue 6 https://doi.org/10.1039/C0CC03898A	journal	January 2011
Hydrogenation of carbon dioxide to methanol using a homogeneous ruthenium–Triphos catalyst: from mechanistic investigations to multiphase catalysis Wesselbaum, Sebastian; Moha, Verena; Meuresch, Markus Chemical Science, Vol. 6, Issue 1 https://doi.org/10.1039/C4SC02087A	journal	January 2015
Formic acid as a hydrogen storage material – development of homogeneous catalysts for selective hydrogen release Mellmann, Dörthe; Sponholz, Peter; Junge, Henrik Chemical Society Reviews, Vol. 45, Issue 14 https://doi.org/10.1039/C5CS00618J	journal	January 2016
Hydrogen energy future with formic acid: a renewable chemical hydrogen storage system Singh, Ashish Kumar; Singh, Suryabhan; Kumar, Abhinav Catalysis Science & Technology, Vol. 6, Issue 1 https://doi.org/10.1039/C5CY01276G	journal	January 2016
Iron catalyzed CO ₂ hydrogenation to formate enhanced by Lewis acid co-catalysts Zhang, Yuanyuan; MacIntosh, Alex D.; Wong, Janice L. Chemical Science, Vol. 6, Issue 7 https://doi.org/10.1039/C5SC01467K	journal	January 2015
Carbon dioxide hydrogenation catalysed by well-defined Mn( i ) PNP pincer hydride complexes Bertini, Federica; Glatz, Mathias; Gorgas, Nikolaus Chemical Science, Vol. 8, Issue 7 https://doi.org/10.1039/C7SC00209B	journal	January 2017
Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry Clavier, Hervé; Nolan, Steven P. Chemical Communications, Vol. 46, Issue 6 https://doi.org/10.1039/b922984a	journal	January 2010
Kinetics and mechanistic analysis of an extremely rapid carbon dioxide fixation reaction Huang, D.; Makhlynets, O. V.; Tan, L. L. Proceedings of the National Academy of Sciences, Vol. 108, Issue 4 https://doi.org/10.1073/pnas.1017430108	journal	January 2011
Efficient Dehydrogenation of Formic Acid Using an Iron Catalyst Boddien, A.; Mellmann, D.; Gartner, F. Science, Vol. 333, Issue 6050 https://doi.org/10.1126/science.1206613	journal	September 2011

Similar Records

Effect of Nucleophilicity on the Kinetics of CO₂ Insertion into Pincer-Supported Nickel Complexes

Journal Article · Mon Oct 22 00:00:00 EDT 2018 · Organometallics · OSTI ID:1566557

Acceleration of CO 2 insertion into metal hydrides: ligand, Lewis acid, and solvent effects on reaction kinetics

Citation Formats

References (59)

Similar Records

Related Subjects

Acceleration of CO ₂ insertion into metal hydrides: ligand, Lewis acid, and solvent effects on reaction kinetics