Thermodynamic Hydricities of Biomimetic Organic Hydride Donors
Abstract
Here, thermodynamic hydricities (ΔGH–) in acetonitrile and dimethyl sulfoxide have been calculated and experimentally measured for several metal-free hydride donors: NADH analogs (BNAH, CN-BNAH, Me-MNAH, HEH), methylene tetrahydromethanopterin analogs (BIMH, CAFH), acridine derivatives (Ph-AcrH, Me2N-AcrH, T-AcrH, 4OH, 2OH, 3NH), and a triarylmethane derivative (6OH). The calculated hydricity values, obtained using density functional theory, showed a reasonably good match (within 3 kcal/mol) with the experimental values, obtained using “potential pKa” and “hydride-transfer” methods. The hydride donor abilities of model compounds were in the 48.7–85.8 kcal/mol (acetonitrile) and 46.9–84.1 kcal/mol (DMSO) range, making them comparable to previously studied first-row transition metal hydride complexes. To evaluate the relevance of entropic contribution to the overall hydricity, Gibbs free energy differences (ΔGH–) obtained in this work were compared with the enthalpy (ΔHH–) values obtained by others. The results indicate that, even though ΔHH– values exhibit the same trends as ΔGH–, the differences between room-temperature ΔGH– and ΔHH– values range from 3 to 9 kcal/mol. This study also reports a new metal-free hydride donor, namely, an acridine-based compound 3NH, whose hydricity exceeds that of NaBH4. Collectively, this work gives a perspective of use metal-free hydride catalysts in fuel-forming and other reduction processes.
- Authors:
-
[3];
[1]
- Univ. of Illinois at Chicago, Chicago, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States)
- Bowling Green State Univ., Bowling Green, OH (United States)
- Univ. of Pittsburgh, Pittsburgh, PA (United States)
- Publication Date:
- Research Org.:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- National Science Foundation (NSF); Petroleum Research Fund (PRF); Ohio Supercomputer Center (OSC); Richard King Mellon Foundation; USDOE
- OSTI Identifier:
- 1467646
- Grant/Contract Number:
- AC02-06CH11357
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 140; Journal Issue: 13; 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
Ilic, Stefan, Kadel, Usha Pandey, Basdogan, Yasemin, Keith, John A., and Glusac, Ksenija D. Thermodynamic Hydricities of Biomimetic Organic Hydride Donors. United States: N. p., 2018.
Web. doi:10.1021/jacs.7b13526.
Ilic, Stefan, Kadel, Usha Pandey, Basdogan, Yasemin, Keith, John A., & Glusac, Ksenija D. Thermodynamic Hydricities of Biomimetic Organic Hydride Donors. United States. https://doi.org/10.1021/jacs.7b13526
Ilic, Stefan, Kadel, Usha Pandey, Basdogan, Yasemin, Keith, John A., and Glusac, Ksenija D. Fri .
"Thermodynamic Hydricities of Biomimetic Organic Hydride Donors". United States. https://doi.org/10.1021/jacs.7b13526. https://www.osti.gov/servlets/purl/1467646.
@article{osti_1467646,
title = {Thermodynamic Hydricities of Biomimetic Organic Hydride Donors},
author = {Ilic, Stefan and Kadel, Usha Pandey and Basdogan, Yasemin and Keith, John A. and Glusac, Ksenija D.},
abstractNote = {Here, thermodynamic hydricities (ΔGH–) in acetonitrile and dimethyl sulfoxide have been calculated and experimentally measured for several metal-free hydride donors: NADH analogs (BNAH, CN-BNAH, Me-MNAH, HEH), methylene tetrahydromethanopterin analogs (BIMH, CAFH), acridine derivatives (Ph-AcrH, Me2N-AcrH, T-AcrH, 4OH, 2OH, 3NH), and a triarylmethane derivative (6OH). The calculated hydricity values, obtained using density functional theory, showed a reasonably good match (within 3 kcal/mol) with the experimental values, obtained using “potential pKa” and “hydride-transfer” methods. The hydride donor abilities of model compounds were in the 48.7–85.8 kcal/mol (acetonitrile) and 46.9–84.1 kcal/mol (DMSO) range, making them comparable to previously studied first-row transition metal hydride complexes. To evaluate the relevance of entropic contribution to the overall hydricity, Gibbs free energy differences (ΔGH–) obtained in this work were compared with the enthalpy (ΔHH–) values obtained by others. The results indicate that, even though ΔHH– values exhibit the same trends as ΔGH–, the differences between room-temperature ΔGH– and ΔHH– values range from 3 to 9 kcal/mol. This study also reports a new metal-free hydride donor, namely, an acridine-based compound 3NH, whose hydricity exceeds that of NaBH4. Collectively, this work gives a perspective of use metal-free hydride catalysts in fuel-forming and other reduction processes.},
doi = {10.1021/jacs.7b13526},
journal = {Journal of the American Chemical Society},
number = 13,
volume = 140,
place = {United States},
year = {2018},
month = {3}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 44 works
Citation information provided by
Web of Science
Web of Science
Figures / Tables:
Scheme 1: Structure of organic hydrides: NADH analogs (BNAH, CN-BNAH, Me-MNAH, HEH), methylene tetrahydromethanopterin analogs (BIMH and CAFH), acridine (Ph-AcrH, Me2N-AcrH, T-AcrH, 4OH, 2OH, 3NH) and triarlymethane (6OH) derivatives.
All figures and tables
(9 total)
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Large-scale applications of NAD(P)-dependent oxidoreductases: recent developments
journal, December 1999
- Hummel, W.
- Trends in Biotechnology, Vol. 17, Issue 12
Reversible interconversion of carbon dioxide and formate by an electroactive enzyme
journal, July 2008
- Reda, T.; Plugge, C. M.; Abram, N. J.
- Proceedings of the National Academy of Sciences, Vol. 105, Issue 31, p. 10654-10658
Biocatalytic Imine Reduction and Reductive Amination of Ketones
journal, May 2015
- Schrittwieser, Joerg H.; Velikogne, Stefan; Kroutil, Wolfgang
- Advanced Synthesis & Catalysis, Vol. 357, Issue 8
Stereocomplementary Bioreduction of α,β-Unsaturated Dicarboxylic Acids and Dimethyl Esters using Enoate Reductases: Enzyme- and Substrate-Based Stereocontrol
journal, December 2007
- Stueckler, Clemens; Hall, Mélanie; Ehammer, Heidemarie
- Organic Letters, Vol. 9, Issue 26
Asymmetric bioreduction of activated C=C bonds using enoate reductases from the old yellow enzyme family
journal, April 2007
- Stuermer, Rainer; Hauer, Bernhard; Hall, Melanie
- Current Opinion in Chemical Biology, Vol. 11, Issue 2
Enantioselective Brønsted Acid Catalyzed Transfer Hydrogenation: Organocatalytic Reduction of Imines
journal, August 2005
- Rueping, Magnus; Sugiono, Erli; Azap, Cengiz
- Organic Letters, Vol. 7, Issue 17
Enantioselective Organocatalytic Transfer Hydrogenation Reactions using Hantzsch Esters
journal, December 2007
- Ouellet, Stéphane G.; Walji, Abbas M.; Macmillan, David W. C.
- Accounts of Chemical Research, Vol. 40, Issue 12
Transfer hydrogenation with Hantzsch esters and related organic hydride donors
journal, January 2012
- Zheng, Chao; You, Shu-Li
- Chemical Society Reviews, Vol. 41, Issue 6
A Highly Enantioselective Brønsted Acid Catalyzed Cascade Reaction: Organocatalytic Transfer Hydrogenation of Quinolines and their Application in the Synthesis of Alkaloids
journal, May 2006
- Rueping, Magnus; Antonchick, Andrey P.; Theissmann, Thomas
- Angewandte Chemie International Edition, Vol. 45, Issue 22
Catalytic Asymmetric Transfer Hydrogenation of α-Ketoesters with Hantzsch Esters
journal, November 2006
- Yang, Jung Woon; List, Benjamin
- Organic Letters, Vol. 8, Issue 24
A Metal-Free Transfer Hydrogenation: Organocatalytic Conjugate Reduction of ?,?-Unsaturated Aldehydes
journal, December 2004
- Yang, Jung Woon; Hechavarria Fonseca, Maria T.; List, Benjamin
- Angewandte Chemie International Edition, Vol. 43, Issue 48
Enantioselective Organocatalytic Hydride Reduction
journal, January 2005
- Ouellet, Stéphane G.; Tuttle, Jamison B.; MacMillan, David W. C.
- Journal of the American Chemical Society, Vol. 127, Issue 1
A new homogeneous electrocatalyst for the reduction of carbon dioxide to methanol at low overpotential
journal, July 1994
- Seshadri, Gayatri; Lin, Chao; Bocarsly, Andrew B.
- Journal of Electroanalytical Chemistry, Vol. 372, Issue 1-2, p. 145-150
Selective Solar-Driven Reduction of CO 2 to Methanol Using a Catalyzed p-GaP Based Photoelectrochemical Cell
journal, May 2008
- Barton, Emily E.; Rampulla, David M.; Bocarsly, Andrew B.
- Journal of the American Chemical Society, Vol. 130, Issue 20
Photochemical and Radiolytic Production of an Organic Hydride Donor with a RuII Complex Containing an NAD+ Model Ligand
journal, May 2007
- Polyansky, Dmitry; Cabelli, Diane; Muckerman, James T.
- Angewandte Chemie International Edition, Vol. 46, Issue 22
Electrochemistry of Acids on Platinum. Application to the Reduction of Carbon Dioxide in the Presence of Pyridinium Ion in Water
journal, November 2013
- Costentin, Cyrille; Canales, Juan Carlos; Haddou, Baptiste
- Journal of the American Chemical Society, Vol. 135, Issue 47
Reduction of CO 2 to Methanol Catalyzed by a Biomimetic Organo-Hydride Produced from Pyridine
journal, November 2014
- Lim, Chern-Hooi; Holder, Aaron M.; Hynes, James T.
- Journal of the American Chemical Society, Vol. 136, Issue 45
Catalytic Reduction of CO 2 by Renewable Organohydrides
journal, December 2015
- Lim, Chern-Hooi; Holder, Aaron M.; Hynes, James T.
- The Journal of Physical Chemistry Letters, Vol. 6, Issue 24
Electrochemical reactivities of pyridinium in solution: consequences for CO2 reduction mechanisms
journal, January 2013
- Keith, John A.; Carter, Emily A.
- Chemical Science, Vol. 4, Issue 4
Theoretical Insights into Electrochemical CO 2 Reduction Mechanisms Catalyzed by Surface-Bound Nitrogen Heterocycles
journal, November 2013
- Keith, John A.; Carter, Emily A.
- The Journal of Physical Chemistry Letters, Vol. 4, Issue 23
Is the Surface Playing a Role during Pyridine-Catalyzed CO 2 Reduction on p-GaP Photoelectrodes?
journal, August 2016
- Lessio, Martina; Senftle, Thomas P.; Carter, Emily A.
- ACS Energy Letters, Vol. 1, Issue 2
Electrochemical Reduction of Aqueous Imidazolium on Pt(111) by Proton Coupled Electron Transfer
journal, November 2014
- Liao, Kuo; Askerka, Mikhail; Zeitler, Elizabeth L.
- Topics in Catalysis, Vol. 58, Issue 1
Comparative Study of Imidazole and Pyridine Catalyzed Reduction of Carbon Dioxide at Illuminated Iron Pyrite Electrodes
journal, July 2012
- Bocarsly, Andrew B.; Gibson, Quinn D.; Morris, Amanda J.
- ACS Catalysis, Vol. 2, Issue 8
A Comparison of Pyridazine and Pyridine as Electrocatalysts for the Reduction of Carbon Dioxide to Methanol
journal, August 2014
- Portenkirchner, Engelbert; Enengl, Christina; Enengl, Sandra
- ChemElectroChem, Vol. 1, Issue 9
The electrochemical reduction of carbon dioxide (CO2) to methanol in the presence of pyridoxine (vitamin B6)
journal, March 2016
- Lee, Jazreen H. Q.; Lauw, Sherman J. L.; Webster, Richard D.
- Electrochemistry Communications, Vol. 64
CO 2 Reduction Catalyzed by Mercaptopteridine on Glassy Carbon
journal, August 2014
- Xiang, Dongmei; Magana, Donny; Dyer, R. Brian
- Journal of the American Chemical Society, Vol. 136, Issue 40
Attempts To Catalyze the Electrochemical CO 2 -to-Methanol Conversion by Biomimetic 2e – + 2H + Transferring Molecules
journal, January 2016
- Saveant, Jean-Michel; Tard, Cédric
- Journal of the American Chemical Society, Vol. 138, Issue 3
Dihydropteridine/Pteridine as a 2H + /2e – Redox Mediator for the Reduction of CO 2 to Methanol: A Computational Study
journal, April 2017
- Lim, Chern-Hooi; Holder, Aaron M.; Hynes, James T.
- The Journal of Physical Chemistry B, Vol. 121, Issue 16
Electrochemical Reduction of Carbon Dioxide to Methanol in the Presence of Benzannulated Dihydropyridine Additives
journal, February 2017
- Giesbrecht, Patrick K.; Herbert, David E.
- ACS Energy Letters, Vol. 2, Issue 3
Photochemical Properties and Reactivity of a Ru Compound Containing an NAD/NADH-Functionalized 1,10-Phenanthroline Ligand
journal, February 2016
- Kobayashi, Katsuaki; Ohtsu, Hideki; Nozaki, Koichi
- Inorganic Chemistry, Vol. 55, Issue 5
[Ir(tpy)(bpy)Cl] as a Photocatalyst for CO 2 Reduction under Visible-Light Irradiation
journal, October 2017
- Sato, Shunsuke; Morikawa, Takeshi
- ChemPhotoChem, Vol. 2, Issue 3
Electrocatalytic Hydrogen Production by an Aluminum(III) Complex: Ligand-Based Proton and Electron Transfer
journal, August 2015
- Thompson, Emily J.; Berben, Louise A.
- Angewandte Chemie International Edition, Vol. 54, Issue 40
Ab Initio Calculations of Thermodynamic Hydricities of Transition-Metal Hydrides in Acetonitrile
journal, August 2007
- Qi, Xiu-Juan; Fu, Yao; Liu, Lei
- Organometallics, Vol. 26, Issue 17
Development of Molecular Electrocatalysts for Energy Storage
journal, February 2014
- DuBois, Daniel L.
- Inorganic Chemistry, Vol. 53, Issue 8
Production of hydrogen by electrocatalysis: making the H–H bond by combining protons and hydrides
journal, January 2014
- Bullock, R. Morris; Appel, Aaron M.; Helm, Monte L.
- Chem. Commun., Vol. 50, Issue 24
Thermodynamic Hydricity of Transition Metal Hydrides
journal, June 2016
- Wiedner, Eric S.; Chambers, Matthew B.; Pitman, Catherine L.
- Chemical Reviews, Vol. 116, Issue 15
Aqueous Hydricity of Late Metal Catalysts as a Continuum Tuned by Ligands and the Medium
journal, February 2016
- Pitman, Catherine L.; Brereton, Kelsey R.; Miller, Alexander J. M.
- Journal of the American Chemical Society, Vol. 138, Issue 7
Aqueous Hydricity from Calculations of Reduction Potential and Acidity in Water
journal, December 2016
- Brereton, Kelsey R.; Bellows, Sarina M.; Fallah, Hengameh
- The Journal of Physical Chemistry B, Vol. 120, Issue 50
Striking Differences in Properties of Geometric Isomers of [Ir(tpy)(ppy)H] + : Experimental and Computational Studies of their Hydricities, Interaction with CO 2 , and Photochemistry
journal, October 2015
- Garg, Komal; Matsubara, Yasuo; Ertem, Mehmed Z.
- Angewandte Chemie International Edition, Vol. 54, Issue 47
Solvation Effects on Transition Metal Hydricity
journal, November 2015
- Tsay, Charlene; Livesay, Brooke N.; Ruelas, Samantha
- Journal of the American Chemical Society, Vol. 137, Issue 44
Tailoring Electrocatalysts for Selective CO 2 or H + Reduction: Iron Carbonyl Clusters as a Case Study
journal, November 2015
- Taheri, Atefeh; Berben, Louise A.
- Inorganic Chemistry, Vol. 55, Issue 2
Rapid Transfer of Hydride Ion from a Ruthenium Complex to C 1 Species in Water
journal, August 2007
- Creutz, Carol; Chou, Mei H.
- Journal of the American Chemical Society, Vol. 129, Issue 33
Bond energies in solution from electrode potentials and thermochemical cycles. A simplified and general approach
journal, May 1993
- Wayner, Danial D. M.; Parker, Vernon D.
- Accounts of Chemical Research, Vol. 26, Issue 5
Measurement of the Hydride Donor Abilities of [HM(diphosphine) 2 ] + Complexes (M = Ni, Pt) by Heterolytic Activation of Hydrogen
journal, March 2002
- Curtis, Calvin J.; Miedaner, Alex; Ellis, William W.
- Journal of the American Chemical Society, Vol. 124, Issue 9
Hydricity of transition-metal hydrides and its role in CO2 reduction
journal, January 2000
- DuBois, Daniel L.; Berning, Douglas E.
- Applied Organometallic Chemistry, Vol. 14, Issue 12
Hydridic character of early transition metal hydride complexes
journal, August 1978
- Labinger, Jay A.; Komadina, Kevin H.
- Journal of Organometallic Chemistry, Vol. 155, Issue 2
Periodic Trends in Metal Hydride Donor Thermodynamics: Measurement and Comparison of the Hydride Donor Abilities of the Series HM(PNP) 2 + (M = Ni, Pd, Pt; PNP = Et 2 PCH 2 N(Me)CH 2 PEt 2 )
journal, February 2004
- Curtis, Calvin J.; Miedaner, Alex; Raebiger, James W.
- Organometallics, Vol. 23, Issue 3
Calculated Hydride Donor Abilities of Five-Coordinate Transition Metal Hydrides [HM(diphosphine) 2 ] + (M = Ni, Pd, Pt) as a Function of the Bite Angle and Twist Angle of Diphosphine Ligands
journal, June 2008
- Nimlos, Mark R.; Chang, Christopher H.; Curtis, Calvin J.
- Organometallics, Vol. 27, Issue 12
Relationship between the bite size of diphosphine ligands and tetrahedral distortions of "square-planar" nickel(II) complexes: stabilization of nickel(I) and palladium(I) complexes using diphosphine ligands with large bites
journal, February 1991
- Miedaner, Alex.; Haltiwanger, R. Curtis.; DuBois, Daniel L.
- Inorganic Chemistry, Vol. 30, Issue 3
Using Ligand Bite Angles To Control the Hydricity of Palladium Diphosphine Complexes
journal, May 2004
- Raebiger, James W.; Miedaner, Alex; Curtis, Calvin J.
- Journal of the American Chemical Society, Vol. 126, Issue 17
Relative Hydride, Proton, and Hydrogen Atom Transfer Abilities of [HM(diphosphine) 2 ]PF 6 Complexes (M = Pt, Ni)
journal, December 1999
- Berning, Douglas E.; Noll, Bruce C.; DuBois, Daniel L.
- Journal of the American Chemical Society, Vol. 121, Issue 49
Free-Energy Relationships between the Proton and Hydride Donor Abilities of [HNi(diphosphine) 2 ] + Complexes and the Half-Wave Potentials of Their Conjugate Bases
journal, April 2001
- Berning, Douglas E.; Miedaner, Alex; Curtis, Calvin J.
- Organometallics, Vol. 20, Issue 9
Thermodynamic Studies of [H 2 Rh(diphosphine) 2 ] + and [HRh(diphosphine) 2 (CH 3 CN)] 2+ Complexes in Acetonitrile
journal, April 2010
- Wilson, Aaron D.; Miller, Alexander J. M.; DuBois, Daniel L.
- Inorganic Chemistry, Vol. 49, Issue 8
Thermodynamic Hydride Donor Abilities of [HW(CO) 4 L] - Complexes (L = PPh 3 , P(OMe) 3 , CO) and Their Reactions with [C 5 Me 5 Re(PMe 3 )(NO)(CO)] +
journal, October 2003
- Ellis, William W.; Ciancanelli, Rebecca; Miller, Susie M.
- Journal of the American Chemical Society, Vol. 125, Issue 40
Comprehensive Thermochemistry of W–H Bonding in the Metal Hydrides CpW(CO) 2 (IMes)H, [CpW(CO) 2 (IMes)H] •+ , and [CpW(CO) 2 (IMes)(H) 2 ] + . Influence of an N -Heterocyclic Carbene Ligand on Metal Hydride Bond Energies
journal, September 2011
- Roberts, John A. S.; Appel, Aaron M.; DuBois, Daniel L.
- Journal of the American Chemical Society, Vol. 133, Issue 37
Hydricities of BzNADH, C 5 H 5 Mo(PMe 3 )(CO) 2 H, and C 5 Me 5 Mo(PMe 3 )(CO) 2 H in Acetonitrile
journal, March 2004
- Ellis, William W.; Raebiger, James W.; Curtis, Calvin J.
- Journal of the American Chemical Society, Vol. 126, Issue 9
CO 2 reduction or HCO 2 − oxidation? Solvent-dependent thermochemistry of a nickel hydride complex
journal, January 2017
- Ceballos, Bianca M.; Tsay, Charlene; Yang, Jenny Y.
- Chemical Communications, Vol. 53, Issue 53
Hydricities of d 6 Metal Hydride Complexes in Water
journal, March 2009
- Creutz, Carol; Chou, Mei H.
- Journal of the American Chemical Society, Vol. 131, Issue 8
Predicting the reactivity of hydride donors in water: thermodynamic constants for hydrogen
journal, January 2015
- Connelly, Samantha J.; Wiedner, Eric S.; Appel, Aaron M.
- Dalton Transactions, Vol. 44, Issue 13
An Iron Electrocatalyst for Selective Reduction of CO 2 to Formate in Water: Including Thermochemical Insights
journal, November 2015
- Taheri, Atefeh; Thompson, Emily J.; Fettinger, James C.
- ACS Catalysis, Vol. 5, Issue 12
Solvent influence on the thermodynamics for hydride transfer from bis(diphosphine) complexes of nickel
journal, January 2016
- Connelly Robinson, Samantha J.; Zall, Christopher M.; Miller, Deanna L.
- Dalton Transactions, Vol. 45, Issue 24
Hydricity of Transition-Metal Hydrides: Thermodynamic Considerations for CO 2 Reduction
journal, January 2018
- Waldie, Kate M.; Ostericher, Andrew L.; Reineke, Mark H.
- ACS Catalysis, Vol. 8, Issue 2
Hydride affinities of carbenium ions in acetonitrile and dimethyl sulfoxide solution
journal, April 1993
- Cheng, Jinpei; Handoo, Kishan L.; Parker, Vernon D.
- Journal of the American Chemical Society, Vol. 115, Issue 7
Free energy hydride affinities of quinones in dimethyl sulfoxide solution
journal, September 1993
- Cheng, Jinpei; Handoo, Kishan L.; Xue, Jieyou
- The Journal of Organic Chemistry, Vol. 58, Issue 19
Hydride Affinities of Organic Cations in Solution.
journal, January 1992
- Parker, Vernon D.; Begtrup, Mikael; de la Hoz, Antonio
- Acta Chemica Scandinavica, Vol. 46
Theoretical Prediction of the Hydride Affinities of Various p - and o -Quinones in DMSO
journal, February 2007
- Zhu, Xiao-Qing; Wang, Chun-Hua; Liang, Hao
- The Journal of Organic Chemistry, Vol. 72, Issue 3
Hydride Affinities of Arylcarbenium Ions and Iminium Ions in Dimethyl Sulfoxide and Acetonitrile
journal, July 1998
- Zhang, Xian-Man; Bruno, Joseph W.; Enyinnaya, Emmeline
- The Journal of Organic Chemistry, Vol. 63, Issue 14
Hydride affinities of organic radicals in solution. A comparison of free radicals and carbenium ions as hydride ion acceptors
journal, June 1993
- Handoo, Kishan L.; Cheng, Jin Pei; Parker, Vernon D.
- Journal of the American Chemical Society, Vol. 115, Issue 12
Hydride, Hydrogen Atom, Proton, and Electron Transfer Driving Forces of Various Five-Membered Heterocyclic Organic Hydrides and Their Reaction Intermediates in Acetonitrile
journal, February 2008
- Zhu, Xiao-Qing; Zhang, Ming-Tian; Yu, Ao
- Journal of the American Chemical Society, Vol. 130, Issue 8
A Thermodynamic and Kinetic Study of Hydride Transfer of a Caffeine Derivative
journal, July 2012
- Han, Xiaozhen; Hao, Weifang; Zhu, Xiao-Qing
- The Journal of Organic Chemistry, Vol. 77, Issue 15
Thermodynamic Diagnosis of the Properties and Mechanism of Dihydropyridine-Type Compounds as Hydride Source in Acetonitrile with “Molecule ID Card”
journal, February 2010
- Zhu, Xiao-Qing; Tan, Yue; Cao, Chao-Tun
- The Journal of Physical Chemistry B, Vol. 114, Issue 5
Kinetics of Hydride Abstractions from 2-Arylbenzimidazolines
journal, October 2009
- Richter, Dorothea; Tan, Yue; Antipova, Anna
- Chemistry - An Asian Journal
Hydride-Donor Abilities of 1,4-Dihydropyridines: A Comparison with π Nucleophiles and Borohydride Anions
journal, March 2009
- Richter, Dorothea; Mayr, Herbert
- Angewandte Chemie International Edition, Vol. 48, Issue 11
The Crystal Structure of an [Fe]-Hydrogenase-Substrate Complex Reveals the Framework for H 2 Activation
journal, August 2009
- Hiromoto, Takeshi; Warkentin, Eberhard; Moll, Johanna
- Angewandte Chemie International Edition, Vol. 48, Issue 35
Systematic optimization of long-range corrected hybrid density functionals
journal, February 2008
- Chai, Jeng-Da; Head-Gordon, Martin
- The Journal of Chemical Physics, Vol. 128, Issue 8
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections
journal, January 2008
- Chai, Jeng-Da; Head-Gordon, Martin
- Physical Chemistry Chemical Physics, Vol. 10, Issue 44
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model
journal, March 1998
- Barone, Vincenzo; Cossi, Maurizio
- The Journal of Physical Chemistry A, Vol. 102, Issue 11
Toward Organic Photohydrides: Excited-State Behavior of 10-Methyl-9-phenyl-9,10-dihydroacridine
journal, May 2013
- Yang, Xin; Walpita, Janitha; Zhou, Dapeng
- The Journal of Physical Chemistry B, Vol. 117, Issue 49
Single-Ion Solvation Free Energies and the Normal Hydrogen Electrode Potential in Methanol, Acetonitrile, and Dimethyl Sulfoxide
journal, January 2007
- Kelly, Casey P.; Cramer, Christopher J.; Truhlar, Donald G.
- The Journal of Physical Chemistry B, Vol. 111, Issue 2
Toward the accurate calculation of pKa values in water and acetonitrile
journal, August 2013
- Muckerman, James T.; Skone, Jonathan H.; Ning, Ming
- Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 1827, Issue 8-9
Threshold photodetachment of
journal, June 1991
- Lykke, K. R.; Murray, K. K.; Lineberger, W. C.
- Physical Review A, Vol. 43, Issue 11
Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993
- Becke, Axel D.
- The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
Effect of the damping function in dispersion corrected density functional theory
journal, March 2011
- Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars
- Journal of Computational Chemistry, Vol. 32, Issue 7
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
journal, January 2005
- Weigend, Florian; Ahlrichs, Reinhart
- Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305
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
journal, May 2009
- Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G.
- The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396
Density-functional approximation for the correlation energy of the inhomogeneous electron gas
journal, June 1986
- Perdew, John P.
- Physical Review B, Vol. 33, Issue 12
The ORCA program system: The ORCA program system
journal, June 2011
- Neese, Frank
- Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 1
Absolute Potential of the Standard Hydrogen Electrode and the Problem of Interconversion of Potentials in Different Solvents
journal, June 2010
- Isse, Abdirisak A.; Gennaro, Armando
- The Journal of Physical Chemistry B, Vol. 114, Issue 23
Sensitization of p-GaP with Monocationic Dyes: The Effect of Dye Excited-State Lifetime on Hole Injection Efficiencies
journal, February 2016
- Ilic, Stefan; Brown, Elizabeth S.; Xie, Yun
- The Journal of Physical Chemistry C, Vol. 120, Issue 6
Synthesis, Structure, and Properties of Azatriangulenium Salts
journal, April 2001
- W. Laursen, Bo; C. Krebs, Frederik
- Chemistry, Vol. 7, Issue 8
Mimicking Nature: Synthetic Nicotinamide Cofactors for C═C Bioreduction Using Enoate Reductases
journal, December 2012
- Paul, Caroline E.; Gargiulo, Serena; Opperman, Diederik J.
- Organic Letters, Vol. 15, Issue 1
Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts
journal, September 2009
- Huang, Sha; Wong, Jesse C. S.; Leung, Adam K. C.
- Tetrahedron Letters, Vol. 50, Issue 35
Photo-induced reduction of pyridinium ions catalysed by zinc(II) tetraphenylporphyrin
journal, January 1979
- Ogata, Yoshiro; Takagi, Katsuhiko; Tanabe, Yuzo
- Journal of the Chemical Society, Perkin Transactions 2, Issue 8
NMR Studies of 2-Aryl Derivatives of Benzimidazole, Benzimidazolium Ion, and Benzimidazoline
journal, January 2009
- Han Lee, In-Sook; Kiu Lee, Chang
- HETEROCYCLES, Vol. 78, Issue 2
Reactions of 8,9-dihydroxanthines with acetylenic compounds. Formation of heteropropellanes.
journal, January 1985
- Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi
- Chemical and Pharmaceutical Bulletin, Vol. 33, Issue 9
Carbonium ion-silane hydride transfer reactions. I. Scope and stereochemistry
journal, May 1968
- Carey, Francis A.; Tremper, Henry S.
- Journal of the American Chemical Society, Vol. 90, Issue 10
Highly selective additions of hydride and organolithium nucleophiles to helical carbenium ions
journal, January 2011
- Guin, Joyram; Besnard, Céline; Pattison, Philip
- Chem. Sci., Vol. 2, Issue 3
Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution
journal, November 1975
- Matthews, Walter S.; Bares, Joseph E.; Bartmess, John E.
- Journal of the American Chemical Society, Vol. 97, Issue 24
Energetics of Multistep versus One-step Hydride Transfer Reactions of Reduced Nicotinamide Adenine Dinucleotide (NADH) Models with Organic Cations and p -Quinones
journal, September 1998
- Cheng, Jin-Pei; Lu, Yun; Zhu, Xiaoqing
- The Journal of Organic Chemistry, Vol. 63, Issue 18
Hydride Dissociation Energies of Six-Membered Heterocyclic Organic Hydrides Predicted by ONIOM-G4Method
journal, December 2011
- Shi, Jing; Huang, Xiong-Yi; Wang, Hua-Jing
- Journal of Chemical Information and Modeling, Vol. 52, Issue 1
Calculation of thermodynamic hydricities and the design of hydride donors for CO2 reduction
journal, July 2012
- Muckerman, J. T.; Achord, P.; Creutz, C.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 39
Elucidation of the Selectivity of Proton-Dependent Electrocatalytic CO 2 Reduction by fac -Re(bpy)(CO) 3 Cl
journal, October 2013
- Keith, John A.; Grice, Kyle A.; Kubiak, Clifford P.
- Journal of the American Chemical Society, Vol. 135, Issue 42
Equilibrium acidities in dimethyl sulfoxide solution
journal, December 1988
- Bordwell, Frederick G.
- Accounts of Chemical Research, Vol. 21, Issue 12
Electrochemistry of NADH/NAD+ analogs. A detailed mechanistic kinetic and thermodynamic analysis of the 10-methylacridan/10-methylacridinium couple in acetonitrile
journal, February 1990
- Hapiot, Philippe; Moiroux, Jacques; Saveant, Jean Michel
- Journal of the American Chemical Society, Vol. 112, Issue 4
Electrochemistry of synthetic analogues of NAD dimers
journal, January 1992
- Anne, A.; Hapiot, P.; Moiroux, J.
- Journal of Electroanalytical Chemistry, Vol. 331, Issue 1-2
Stable free radicals. 12. New aspects of the behavior of 1-alkyl-4-(carboalkoxy)- and 1-alkyl-4-carbamidopyridinyl radicals in solution and in thin films
journal, August 1981
- Hermolin, Joshua; Levin, Menachem; Kosower, Edward M.
- Journal of the American Chemical Society, Vol. 103, Issue 16
Electrosynthesis of Imidazolium Carboxylates
journal, August 2013
- de Robillard, Guillaume; Devillers, Charles H.; Kunz, Doris
- Organic Letters, Vol. 15, Issue 17
Arylethynylacridines: electrochemiluminescence and photophysical properties
journal, January 2004
- Elangovan, Arumugasamy; Chiu, Hsing-Hua; Yang, Shu-Wen
- Organic & Biomolecular Chemistry, Vol. 2, Issue 21
Electrochemical reduction of an imidazolium cation: a convenient preparation of imidazol-2-ylidenes and their observation in an ionic liquid
journal, January 2004
- Gorodetsky, Brian; Ramnial, Taramatee; Branda, Neil R.
- Chemical Communications, Issue 17
Electrochemical Characterization of Azolium Salts
journal, June 2014
- Ogawa, Kelli A.; Boydston, Andrew J.
- Chemistry Letters, Vol. 43, Issue 6
Electrochemistry of the 9-phenyl-10-methyl-acridan/acridinium redox system; a high-potential NADH/NAD + analogue
journal, January 1985
- Koper, N. W.; Jonker, S. A.; Verhoeven, J. W.
- Recueil des Travaux Chimiques des Pays-Bas, Vol. 104, Issue 11
Establishing the Hydride Donor Abilities of Main Group Hydrides
journal, May 2015
- Heiden, Zachariah M.; Lathem, A. Paige
- Organometallics, Vol. 34, Issue 10
Thermodynamic and Kinetic Hydricity of Ruthenium(II) Hydride Complexes
journal, September 2012
- Matsubara, Yasuo; Fujita, Etsuko; Doherty, Mark D.
- Journal of the American Chemical Society, Vol. 134, Issue 38
Structure sensitivity of the Marcus .lambda. for hydride transfer between NAD+ analogs
journal, January 1988
- Kreevoy, Maurice M.; Ostovic, Drazen.; Lee, In Sook Han.
- Journal of the American Chemical Society, Vol. 110, Issue 2
Formal Transfers of Hydride from Carbon−Hydrogen Bonds. Generation of H 2 from Orthoformamides Designed To Undergo Intramolecular Protonolyses of Activated Carbon−Hydrogen Bonds
journal, January 1996
- Brunet, Philippe; Wuest, James D.
- The Journal of Organic Chemistry, Vol. 61, Issue 6
The Crystal Structure of [Fe]-Hydrogenase Reveals the Geometry of the Active Site
journal, July 2008
- Shima, S.; Pilak, O.; Vogt, S.
- Science, Vol. 321, Issue 5888
The coordination chemistry of organo-hydride donors: new prospects for efficient multi-electron reduction
journal, January 2013
- McSkimming, Alex; Colbran, Stephen B.
- Chemical Society Reviews, Vol. 42, Issue 12
Development of Molecular Electrocatalysts for CO2 Reduction and H2 Production/Oxidation
journal, December 2009
- Rakowski Dubois, M.; Dubois, Daniel L.
- Accounts of Chemical Research, Vol. 42, Issue 12, p. 1974-1982
Complexes of earth-abundant metals for catalytic electrochemical hydrogen generation under aqueous conditions
journal, January 2013
- Thoi, V. Sara; Sun, Yujie; Long, Jeffrey R.
- Chem. Soc. Rev., Vol. 42, Issue 6
Trialkylborane-Assisted CO 2 Reduction by Late Transition Metal Hydrides
journal, August 2011
- Miller, Alexander J. M.; Labinger, Jay A.; Bercaw, John E.
- Organometallics, Vol. 30, Issue 16
Cyclopentadiene-mediated hydride transfer from rhodium complexes
journal, January 2016
- Pitman, C. L.; Finster, O. N. L.; Miller, A. J. M.
- Chemical Communications, Vol. 52, Issue 58
Photoswitchable Hydride Transfer from Iridium to 1-Methylnicotinamide Rationalized by Thermochemical Cycles
journal, October 2014
- Barrett, Seth M.; Pitman, Catherine L.; Walden, Andrew G.
- Journal of the American Chemical Society, Vol. 136, Issue 42
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
journal, July 2007
- Fraze, Kendra; Wilson, Aaron D.; Appel, Aaron M.
- Organometallics, Vol. 26, Issue 16
Mechanistic Insights into Catalytic H 2 Oxidation by Ni Complexes Containing a Diphosphine Ligand with a Positioned Amine Base
journal, April 2009
- Yang, Jenny Y.; Bullock, R. Morris; Shaw, Wendy J.
- Journal of the American Chemical Society, Vol. 131, Issue 16
Electrocatalytic Oxidation of Formate by [Ni(P R 2 N R′ 2 ) 2 (CH 3 CN)] 2+ Complexes
journal, August 2011
- Galan, Brandon R.; Schöffel, Julia; Linehan, John C.
- Journal of the American Chemical Society, Vol. 133, Issue 32
Two Pathways for Electrocatalytic Oxidation of Hydrogen by a Nickel Bis(diphosphine) Complex with Pendant Amines in the Second Coordination Sphere
journal, June 2013
- Yang, Jenny Y.; Smith, Stuart E.; Liu, Tianbiao
- Journal of the American Chemical Society, Vol. 135, Issue 26
Open questions in ferredoxin-NADP+ reductase catalytic mechanism
journal, May 2003
- Carrillo, Nestor; Ceccarelli, Eduardo A.
- European Journal of Biochemistry, Vol. 270, Issue 9
One-Electron and Two-Electron Transfers in Electrochemistry and Homogeneous Solution Reactions
journal, July 2008
- Evans, Dennis H.
- Chemical Reviews, Vol. 108, Issue 7
Electron-transfer reactions and associated conformational changes. Extended redox series for some bianthrones, lucigenin, and dixanthylene
journal, September 1982
- Evans, Dennis H.; Busch, Robert W.
- Journal of the American Chemical Society, Vol. 104, Issue 19
Works referencing / citing this record:
Conformational analysis of diols: Role of the linker on the relative orientation of hydroxyl groups
journal, June 2019
- Zoric, Marija R.; Singh, Varun; Zeller, Matthias
- Journal of Physical Organic Chemistry, Vol. 32, Issue 10
Importance of proton-coupled electron transfer in cathodic regeneration of organic hydrides
journal, January 2019
- Ilic, Stefan; Alherz, Abdulaziz; Musgrave, Charles B.
- Chemical Communications, Vol. 55, Issue 39
The visible-light-driven transfer hydrogenation of nicotinamide cofactors with a robust ruthenium complex photocatalyst
journal, January 2020
- Dong, Wenjin; Tang, Jie; Zhao, Lijun
- Green Chemistry, Vol. 22, Issue 7
Diazaphosphinanes as hydride, hydrogen atom, proton or electron donors under transition-metal-free conditions: thermodynamics, kinetics, and synthetic applications
journal, January 2020
- Zhang, Jingjing; Yang, Jin-Dong; Cheng, Jin-Pei
- Chemical Science, Vol. 11, Issue 14
Unambiguous hydrogenation of CO 2 by coinage-metal hydride anions: an intuitive idea based on in silico experiments
journal, January 2019
- Habib, Md; Sarkar, Ritabrata; Biswas, Santu
- Physical Chemistry Chemical Physics, Vol. 21, Issue 14
Snapshots of a Migrating H-Atom: Characterization of a Reactive Iron(III) Indenide Hydride and its Nearly Isoenergetic Ring-Protonated Iron(I) Isomer
journal, September 2019
- Drover, Marcus W.; Schild, Dirk J.; Oyala, Paul H.
- Angewandte Chemie International Edition, Vol. 58, Issue 43
Snapshots of a Migrating H‐Atom: Characterization of a Reactive Iron(III) Indenide Hydride and its Nearly Isoenergetic Ring‐Protonated Iron(I) Isomer
journal, September 2019
- Drover, Marcus W.; Schild, Dirk J.; Oyala, Paul H.
- Angewandte Chemie, Vol. 131, Issue 43
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.