Role of High-Spin Species and Pendant Amines in Electrocatalytic Alcohol Oxidation by a Nickel Phosphine Complex

Gunasekara, Thilina; Tong, Yicheng; Speelman, Amy L.; Erickson, Jeremy D.; Appel, Aaron M.; Hall, Michael B.; Wiedner, Eric S.

doi:10.1021/acscatal.1c05509

Title: Role of High-Spin Species and Pendant Amines in Electrocatalytic Alcohol Oxidation by a Nickel Phosphine Complex

Journal Article · 09 February 2022 · ACS Catalysis

DOI: https://doi.org/10.1021/acscatal.1c05509 · OSTI ID:1854600

Gunasekara, Thilina ^[1]; Tong, Yicheng ^[2];

^[1]; Erickson, Jeremy D. ^[1];

^[1];

^[2];

^[1]

Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Texas A & M Univ., College Station, TX (United States)

We report the development of active and efficient electrocatalysts for oxidation of alcohols using earth-abundant metals will aid the progress towards a renewable energy economy. Here we present a detailed mechanistic study of electrocatalytic benzyl alcohol oxidation by a molecular nickel complex containing pendant amines using a combination of kinetic studies, NMR spectroscopy, and density functional theory. The catalyst preferentially binds alcohol in high-spin octahedral geometry, but this complex is not readily deprotonated by exogeneous base and inhibits catalysis. Dissociation of one or more solvent ligands returns the complex to a low-spin state that can be deprotonated. Kinetic modeling indicates the off-cycle high-spin intermediate lowers the catalytic turnover frequency by a factor of eight, suggesting that substantial gains in activity can be attained by improvements to the catalyst coordination geometry. In a second finding, we demonstrate the pendant amine of the catalyst only functions as a proton relay for the potential-determining step, oxidation of a nickel hydride intermediate, but does not have a substantial impact on the overall rate for oxidation of benzyl alcohol to benzaldehyde. This result contradicts the common expectation for pendant amines to participate in rate-limiting proton transfer reactions.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Welch Foundation

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1854600

Report Number(s):: PNNL-SA-168765

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 5 Vol. 12; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (70)

From Structural Models of Galactose Oxidase to Homogeneous Catalysis: Efficient Aerobic Oxidation of Alcohols Chaudhuri, Phalguni; Hess, Martina; Flörke, Ulrich Angewandte Chemie International Edition, Vol. 37, Issue 16 https://doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D	journal	September 1998
Aerobic Oxidation of Primary Alcohols by a New Mononuclear CuII-Radical Catalyst Chaudhuri, Phalguni; Hess, Martina; Weyhermüller, Thomas Angewandte Chemie International Edition, Vol. 38, Issue 8 https://doi.org/10.1002/(SICI)1521-3773(19990419)38:8<1095::AID-ANIE1095>3.0.CO;2-I	journal	April 1999
Elements of Molecular and Biomolecular Electrochemistry Savéant, Jean-Michel https://doi.org/10.1002/0471758078	book	January 2006
Multielectron, Multistep Molecular Catalysis of Electrochemical Reactions: Benchmarking of Homogeneous Catalysts Costentin, Cyrille; Savéant, Jean-Michel ChemElectroChem, Vol. 1, Issue 7 https://doi.org/10.1002/celc.201300263	journal	June 2014
Determining the Overpotential of Electrochemical Fuel Synthesis Mediated by Molecular Catalysts: Recommended Practices, Standard Reduction Potentials, and Challenges Stratakes, Bethany M.; Dempsey, Jillian L.; Miller, Alexander J. M. ChemElectroChem, Vol. 8, Issue 22 https://doi.org/10.1002/celc.202100576	journal	August 2021
Methanol for Renewable Energy Storage and Utilization Räuchle, Konstantin; Plass, Ludolf; Wernicke, Hans-Jürgen Energy Technology, Vol. 4, Issue 1 https://doi.org/10.1002/ente.201500322	journal	January 2016
Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21+G basis set for first-row elements, Li-F Clark, Timothy; Chandrasekhar, Jayaraman; Spitznagel, G�nther W. Journal of Computational Chemistry, Vol. 4, Issue 3 https://doi.org/10.1002/jcc.540040303	journal	October 1983
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
Potential-sweep chronoamperometry: Kinetic currents for first-order chemical reaction parallel to electron-transfer process (catalytic currents) Saveant, J. M.; Vianello, E. Electrochimica Acta, Vol. 10, Issue 9 https://doi.org/10.1016/0013-4686(65)80003-2	journal	September 1965
Enzyme kinetics: partial and complete uncompetitive inhibition Whiteley, Chris G. Biochemical Education, Vol. 28, Issue 3 https://doi.org/10.1016/S0307-4412(00)00029-7	journal	May 2000
Enzyme kinetics: Partial and complete competitive inhibition Whiteley, Chris G. Biochemical Education, Vol. 25, Issue 3 https://doi.org/10.1016/S0307-4412(97)00070-8	journal	July 1997
A review of anode catalysis in the direct methanol fuel cell Liu, Hansan; Song, Chaojie; Zhang, Lei Journal of Power Sources, Vol. 155, Issue 2, p. 95-110 https://doi.org/10.1016/j.jpowsour.2006.01.030	journal	April 2006
Electrocatalysts for electrooxidation of direct alcohol fuel cell: chemistry and applications Siwal, S. S.; Thakur, S.; Zhang, Q. B. Materials Today Chemistry, Vol. 14 https://doi.org/10.1016/j.mtchem.2019.06.004	journal	December 2019
Theory of Stationary Electrode Polarography. Single Scan and Cyclic Methods Applied to Reversible, Irreversible, and Kinetic Systems. Nicholson, R. S.; Shain, Irving Analytical Chemistry, Vol. 36, Issue 4, p. 706-723 https://doi.org/10.1021/ac60210a007	journal	April 1964
Electrocatalytic Alcohol Oxidation with Iron-Based Acceptorless Alcohol Dehydrogenation Catalyst McLoughlin, Elizabeth A.; Matson, Benjamin D.; Sarangi, Ritimukta Inorganic Chemistry, Vol. 59, Issue 2 https://doi.org/10.1021/acs.inorgchem.9b03230	journal	December 2019
Molecular Electrocatalysts for Alcohol Oxidation: Insights and Challenges for Catalyst Design Cook, Andrew W.; Waldie, Kate M. ACS Applied Energy Materials, Vol. 3, Issue 1 https://doi.org/10.1021/acsaem.9b01820	journal	November 2019
Combining Benzyl Alcohol Oxidation Saturation Kinetics and Hammett Studies as Mechanistic Tools for Examining Supported Metal Catalysts Mahdavi-Shakib, Akbar; Sempel, Janine; Babb, Lauren ACS Catalysis, Vol. 10, Issue 17 https://doi.org/10.1021/acscatal.0c02212	journal	August 2020
Electrochemically Regenerable Hydrogen Atom Acceptors: Mediators in Electrocatalytic Alcohol Oxidation Reactions McLoughlin, Elizabeth A.; Armstrong, Keith C.; Waymouth, Robert M. ACS Catalysis, Vol. 10, Issue 19 https://doi.org/10.1021/acscatal.0c03240	journal	September 2020
Electrocatalytic Oxidation of Alcohol with Cobalt Triphosphine Complexes Heins, Spencer P.; Schneider, Patrick E.; Speelman, Amy L. ACS Catalysis, Vol. 11, Issue 11 https://doi.org/10.1021/acscatal.1c00781	journal	May 2021
Interpreting the Electrocatalytic Voltammetry of Homogeneous Catalysts by the Foot of the Wave Analysis and Its Wider Implications Wang, Vincent C. -C.; Johnson, Ben A. ACS Catalysis, Vol. 9, Issue 8 https://doi.org/10.1021/acscatal.9b00850	journal	June 2019
Pd-Catalyzed C–N Coupling Reactions Facilitated by Organic Bases: Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation of Weakly Binding Amines Dennis, Joseph M.; White, Nicholas A.; Liu, Richard Y. ACS Catalysis, Vol. 9, Issue 5 https://doi.org/10.1021/acscatal.9b00981	journal	March 2019
Mechanism of Palladium-Catalyzed C–N Coupling with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) as a Base Kim, Seoung-Tae; Pudasaini, Bimal; Baik, Mu-Hyun ACS Catalysis, Vol. 9, Issue 8 https://doi.org/10.1021/acscatal.9b02373	journal	June 2019
Determining the Overpotential for a Molecular Electrocatalyst Appel, Aaron M.; Helm, Monte L. ACS Catalysis, Vol. 4, Issue 2 https://doi.org/10.1021/cs401013v	journal	December 2013
Computing Free Energy Landscapes: Application to Ni-based Electrocatalysts with Pendant Amines for H ₂ Production and Oxidation Chen, Shentan; Ho, Ming-Hsun; Bullock, R. Morris ACS Catalysis, Vol. 4, Issue 1 https://doi.org/10.1021/cs401104w	journal	December 2013
Catalytic Oxidation of Alcohol via Nickel Phosphine Complexes with Pendant Amines Weiss, Charles J.; Das, Parthapratim; Miller, Deanna L. ACS Catalysis, Vol. 4, Issue 9 https://doi.org/10.1021/cs500853f	journal	August 2014
Nonlinear Hammett relationships Schreck, James O. Journal of Chemical Education, Vol. 48, Issue 2 https://doi.org/10.1021/ed048p103	journal	February 1971
Synthesis, Structure, and Redox and Catalytic Properties of a New Family of Ruthenium Complexes Containing the Tridentate bpea Ligand Rodríguez, Montserrat; Romero, Isabel; Llobet, Antoni Inorganic Chemistry, Vol. 40, Issue 17 https://doi.org/10.1021/ic010064q	journal	August 2001
[Ni(Et ₂ PCH ₂ NMeCH ₂ PEt ₂ ) ₂ ] ²⁺ as a Functional Model for Hydrogenases Curtis, Calvin J.; Miedaner, Alex; Ciancanelli, Rebecca Inorganic Chemistry, Vol. 42, Issue 1 https://doi.org/10.1021/ic020610v	journal	January 2003
Iron-Only Hydrogenase Mimics. Thermodynamic Aspects of the Use of Electrochemistry to Evaluate Catalytic Efficiency for Hydrogen Generation Felton, Greg A. N.; Glass, Richard S.; Lichtenberger, Dennis L. Inorganic Chemistry, Vol. 45, Issue 23 https://doi.org/10.1021/ic060984e	journal	November 2006
H ₂ Evolution and Molecular Electrocatalysts: Determination of Overpotentials and Effect of Homoconjugation Fourmond, Vincent; Jacques, Pierre-André; Fontecave, Marc Inorganic Chemistry, Vol. 49, Issue 22 https://doi.org/10.1021/ic101187v	journal	November 2010
Direct Determination of Equilibrium Potentials for Hydrogen Oxidation/Production by Open Circuit Potential Measurements in Acetonitrile Roberts, John A. S.; Bullock, R. Morris Inorganic Chemistry, Vol. 52, Issue 7 https://doi.org/10.1021/ic302461q	journal	June 2012
Phosphine-Based Platinum(II) Hydroxo and Oxo Complexes ¹ Li, Jian Jun; Li, Wei; Sharp, Paul R. Inorganic Chemistry, Vol. 35, Issue 3 https://doi.org/10.1021/ic950593s	journal	January 1996
Steric Modulation of Electrocatalytic Benzyl Alcohol Oxidation by [Ru(trpy)(R ₂ dppi)(O)] ²⁺ Complexes Catalano, Vincent J.; Heck, Ryan A.; Immoos, Chad E. Inorganic Chemistry, Vol. 37, Issue 9 https://doi.org/10.1021/ic971027v	journal	May 1998
Ligand-Based Redox Isomers of [Zn ^II (C ₂₈ H ₄₀ NO ₂ ) ₂ ]: Molecular and Electronic Structures of a Diamagnetic Green and a Paramagnetic Red Form Chaudhuri, Phalguni; Hess, Martina; Hildenbrand, Knut Inorganic Chemistry, Vol. 38, Issue 12 https://doi.org/10.1021/ic990003g	journal	May 1999
Cone angles for amine ligands. X-ray crystal structures and equilibrium measurements for ammonia, ethylamine, diethylamine, and triethylamine complexes with the [bis(dimethylphosphino)ethane]methylpalladium(II) cation Seligson, Allen L.; Trogler, William C. Journal of the American Chemical Society, Vol. 113, Issue 7 https://doi.org/10.1021/ja00007a028	journal	March 1991
Effects of peripheral steric constraints and metal ion size on the structure of three five-coordinate macrocyclic ligand complexes of the type [M(C22H22N4)X], M = cobalt(III), iron(III), manganese(II); X = iodine, chlorine, triethylamine Weiss, Marvin C.; Bursten, Bruce; Peng, Shie-Ming Journal of the American Chemical Society, Vol. 98, Issue 25 https://doi.org/10.1021/ja00441a024	journal	December 1976
Self-consistent molecular orbital methods. 21. Small split-valence basis sets for first-row elements Binkley, J. Stephen; Pople, John A.; Hehre, Warren J. Journal of the American Chemical Society, Vol. 102, Issue 3 https://doi.org/10.1021/ja00523a008	journal	January 1980
Chemically catalyzed net electrochemical oxidation of alcohols, aldehydes, and unsaturated hydrocarbons using the system (trpy)(bpy)Ru(OH2)2+/(trpy)(bpy)RuO2+ Moyer, Bruce A.; Thompson, Mark S.; Meyer, Thomas J. Journal of the American Chemical Society, Vol. 102, Issue 7 https://doi.org/10.1021/ja00527a030	journal	March 1980
Two Pathways for Electrocatalytic Oxidation of Hydrogen by a Nickel Bis(diphosphine) Complex with Pendant Amines in the Second Coordination Sphere Yang, Jenny Y.; Smith, Stuart E.; Liu, Tianbiao Journal of the American Chemical Society, Vol. 135, Issue 26 https://doi.org/10.1021/ja400705a	journal	June 2013
The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C–N Cross-Coupling Liu, Richard Y.; Dennis, Joseph M.; Buchwald, Stephen L. Journal of the American Chemical Society, Vol. 142, Issue 9 https://doi.org/10.1021/jacs.0c00286	journal	February 2020
Determining Proton-Coupled Standard Potentials and X–H Bond Dissociation Free Energies in Nonaqueous Solvents Using Open-Circuit Potential Measurements Wise, Catherine F.; Agarwal, Rishi G.; Mayer, James M. Journal of the American Chemical Society, Vol. 142, Issue 24 https://doi.org/10.1021/jacs.0c01032	journal	May 2020
Electron-Rich Phenoxyl Mediators Improve Thermodynamic Performance of Electrocatalytic Alcohol Oxidation with an Iridium Pincer Complex Galvin, Conor M.; Waymouth, Robert M. Journal of the American Chemical Society, Vol. 142, Issue 45 https://doi.org/10.1021/jacs.0c09605	journal	November 2020
Electrooxidation of Ethanol and Methanol Using the Molecular Catalyst [{Ru ₄ O ₄ (OH) ₂ (H ₂ O) ₄ }(γ-SiW ₁₀ O ₃₆ ) ₂ ] ^10– Liu, YuPing; Zhao, Shu-Feng; Guo, Si-Xuan Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.5b11408	journal	February 2016
Electrocatalytic Alcohol Oxidation with Ruthenium Transfer Hydrogenation Catalysts Waldie, Kate M.; Flajslik, Kristen R.; McLoughlin, Elizabeth Journal of the American Chemical Society, Vol. 139, Issue 2 https://doi.org/10.1021/jacs.6b09705	journal	January 2017
Theoretical Analysis of the Sequential Proton-Coupled Electron Transfer Mechanisms for H ₂ Oxidation and Production Pathways Catalyzed by Nickel Molecular Electrocatalysts Fernandez, Laura E.; Horvath, Samantha; Hammes-Schiffer, Sharon The Journal of Physical Chemistry C, Vol. 116, Issue 4 https://doi.org/10.1021/jp210690q	journal	January 2012
Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G. The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396 https://doi.org/10.1021/jp810292n	journal	May 2009
Thermodynamic Properties of the Ni−H Bond in Complexes of the Type [HNi(P ₂ ^R N ₂ ^R ^‘ ) ₂ ](BF ₄ ) and Evaluation of Factors That Control Catalytic Activity for Hydrogen Oxidation/Production Fraze, Kendra; Wilson, Aaron D.; Appel, Aaron M. Organometallics, Vol. 26, Issue 16 https://doi.org/10.1021/om070143v	journal	July 2007
Comparison of Cobalt and Nickel Complexes with Sterically Demanding Cyclic Diphosphine Ligands: Electrocatalytic H ₂ Production by [Co(P ^t ^Bu ₂ N ^Ph ₂ )(CH ₃ CN) ₃ ](BF ₄ ) ₂ ^† Wiedner, Eric S.; Yang, Jenny Y.; Dougherty, William G. Organometallics, Vol. 29, Issue 21 https://doi.org/10.1021/om100395r	journal	November 2010
Iron and Ruthenium Heterobimetallic Carbonyl Complexes as Electrocatalysts for Alcohol Oxidation: Electrochemical and Mechanistic Studies Serra, Daniel; Correia, Marie C.; McElwee-White, Lisa Organometallics, Vol. 30, Issue 21 https://doi.org/10.1021/om101070z	journal	November 2011
(N-Heterocyclic Carbene)PdCl ₂ (TEA) Complexes: Studies on the Effect of the “Throw-Away” Ligand in Catalytic Activity Chen, Ming-Tsz; Vicic, David A.; Turner, Michael L. Organometallics, Vol. 30, Issue 18 https://doi.org/10.1021/om200699p	journal	September 2011
Stabilization of Nickel Complexes with Ni ⁰ ···H–N Bonding Interactions Using Sterically Demanding Cyclic Diphosphine Ligands Wiedner, Eric S.; Yang, Jenny Y.; Chen, Shentan Organometallics, Vol. 31, Issue 1 https://doi.org/10.1021/om200709z	journal	December 2011
The Role of Gold Acetylides as a Selectivity Trigger and the Importance of gem -Diaurated Species in the Gold-Catalyzed Hydroarylating-Aromatization of Arene-Diynes Hashmi, A. Stephen K.; Braun, Ingo; Rudolph, Matthias Organometallics, Vol. 31, Issue 2 https://doi.org/10.1021/om200946m	journal	January 2012
Synthesis of Low-Valent Nickel Complexes in Aqueous Media, Mechanistic Insights, and Selected Applications Morales-Becerril, Illán; Flores-Álamo, Marcos; Tlahuext-Aca, Adrián Organometallics, Vol. 33, Issue 23 https://doi.org/10.1021/om500767p	journal	November 2014
Monomeric Alkoxo and Amido Methylnickel(II) Complexes. Synthesis and Heterocumulene Insertion Chemistry Cámpora, Juan; Matas, Inmaculada; Palma, Pilar Organometallics, Vol. 26, Issue 15 https://doi.org/10.1021/om7002909	journal	June 2007
Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators Badalyan, Artavazd; Stahl, Shannon S. Nature, Vol. 535, Issue 7612 https://doi.org/10.1038/nature18008	journal	June 2016
Aerial oxidation of primary alcohols and amines catalyzed by Cu( ii ) complexes of 2,2′-selenobis(4,6-di-tert-butylphenol) providing [O,Se,O]-donor atoms Paine, Tapan K.; Weyhermüller, Thomas; Wieghardt, Karl Dalton Trans., Issue 14 https://doi.org/10.1039/B403953J	journal	January 2004
Recycling of carbon dioxide to methanol and derived products – closing the loop Goeppert, Alain; Czaun, Miklos; Jones, John-Paul Chem. Soc. Rev., Vol. 43, Issue 23 https://doi.org/10.1039/C4CS00122B	journal	January 2014
Nickel phosphine catalysts with pendant amines for electrocatalytic oxidation of alcohols Weiss, Charles J.; Wiedner, Eric S.; Roberts, John A. S. Chemical Communications, Vol. 51, Issue 28 https://doi.org/10.1039/C5CC01107H	journal	January 2015
Room temperature, solventless telomerization of isoprene with alcohols using (N-heterocyclic carbene)–palladium catalysts Maluenda, Irene; Chen, Ming-Tsz; Guest, Daniel Catalysis Science & Technology, Vol. 5, Issue 3 https://doi.org/10.1039/C5CY00058K	journal	January 2015
Efficient nickel catalyst for coupling of acetonitrile with aldehydes Fan, Lei; Ozerov, Oleg. V. Chemical Communications, Issue 35 https://doi.org/10.1039/b505778g	journal	January 2005
Ligand influence in the selective gold-mediated synthesis of allenes Nun, Pierrick; Gaillard, Sylvain; Slawin, Alexandra M. Z. Chemical Communications, Vol. 46, Issue 48 https://doi.org/10.1039/c0cc03071f	journal	January 2010
Highly selective electrocatalytic dehydrogenation at low applied potential catalyzed by an Ir organometallic complex Bonitatibus, Peter J.; Rainka, Matthew P.; Peters, Andrea J. Chemical Communications, Vol. 49, Issue 90 https://doi.org/10.1039/c3cc46051g	journal	January 2013
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Insights into proton-coupled electron transfer mechanisms of electrocatalytic H2 oxidation and production Horvath, S.; Fernandez, L. E.; Soudackov, A. V. Proceedings of the National Academy of Sciences, Vol. 109, Issue 39 https://doi.org/10.1073/pnas.1118333109	journal	April 2012
Renewable electricity storage using electrolysis Yan, Zhifei; Hitt, Jeremy L.; Turner, John A. Proceedings of the National Academy of Sciences, Vol. 117, Issue 23 https://doi.org/10.1073/pnas.1821686116	journal	December 2019
Syntheses, Characterization and Crystal Structure of Tetramethyldibenzotetraaza[14]-Annulene Zinc(Ii) Complexes Containing an Axial base Wang, Zenglin; Sakata, Kazunori; Hashimoto, Mamoru Journal of Coordination Chemistry, Vol. 48, Issue 4 https://doi.org/10.1080/00958979908023594	journal	October 1999
(5-Bromo-2-oxidoacetophenone 4-chlorobenzoylhydrazido)(triethylamine)nickel(II) Ali, Hapipah; Khamis, Nur Ashikin; Yamin, Bohari M. Acta Crystallographica Section E Structure Reports Online, Vol. 60, Issue 10 https://doi.org/10.1107/S1600536804023554	journal	September 2004
Analysis of the substrate inhibition of complete and partial types Yoshino, Masataka; Murakami, Keiko SpringerPlus, Vol. 4, Issue 1 https://doi.org/10.1186/s40064-015-1082-8	journal	June 2015
Liquid fuel cells Soloveichik, Grigorii L. Beilstein Journal of Nanotechnology, Vol. 5 https://doi.org/10.3762/bjnano.5.153	journal	January 2014

Linked Research (2)

Similar Records

Catalytic Oxidation of Alcohol via Nickel Phosphine Complexes with Pendant Amines

Journal Article · 2014 · ACS Catalysis, 4(9):2951-2958 · OSTI ID:1177318

Weiss, Charles J.; Das, Partha Pratim; Higgins, Deanna LM; +2 more

Nickel Phosphine Catalysts with Pendant Amines for Electrocatalytic Oxidation of Alcohols

Journal Article · 2015 · Chemical Communications, 51(28):6172-6174 · OSTI ID:1182935

Weiss, Charles J.; Wiedner, Eric S.; Roberts, John A.; +1 more

Coordination Chemistry of Phosphine Ligands with Pendant Amines

Book · 2021 · OSTI ID:1869786

DuBois, Daniel L.; Wiedner, Eric S.; Bullock, Ronald M.

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alcohol oxidation
electrocatalysis
electrooxidation
mechanism
nickel
pendant amine

CCDC 2122977: Experimental Crystal Structure Determination Thilina, Gunasekara,; Yicheng, Tong,; L., Speelman, Amy https://doi.org/10.5517/ccdc.csd.cc29844w The current record is supplemented by this dataset	dataset	January 2023
CCDC 2265270: Experimental Crystal Structure Determination Thilina, Gunasekara,; Yicheng, Tong,; L., Speelman, Amy https://doi.org/10.5517/ccdc.csd.cc2g167z The current record is supplemented by this dataset	dataset	January 2023

Title: Role of High-Spin Species and Pendant Amines in Electrocatalytic Alcohol Oxidation by a Nickel Phosphine Complex

Citation Formats

References (70)

Linked Research (2)

Similar Records

Related Subjects