Hydrolysis of Acetamide on Low-Index CeO2 Surfaces: Ceria as a Deamidation and General De-esterification Catalyst

Bhasker-Ranganath, Suman; Xu, Ye

doi:10.1021/acscatal.2c02514

Hydrolysis of Acetamide on Low-Index CeO₂ Surfaces: Ceria as a Deamidation and General De-esterification Catalyst

Journal Article · Fri Aug 05 00:00:00 EDT 2022 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.2c02514· OSTI ID:2470071

Bhasker-Ranganath, Suman ^[1]; ^[1]

Louisiana State Univ., Baton Rouge, LA (United States)

Using DFT calculations and acetamide as the main example, we show that ceria is a potential catalyst for the hydrolysis of amide and similar bonds. The overall reaction is endergonic in the gas phase, yielding acetic acid and ammonia, but is slightly exergonic in the aqueous phase, which facilitates ionization of the products (CH₃COO^– and NH₄⁺). Neighboring Ce and O sites on the CeO₂(111), (110), and (100) facets are conducive to the formation of an activated metastable tetrahedral intermediate (TI) complex, followed by C–N bond scission. With van der Waals and solvation effects taken into account, the overall reaction energetics is found to be most favorable on the (111) facet as desorption of acetic acid is much more uphill energetically on (110) and (100). We further suggest that the Ce–O–Ce sites on ceria surfaces can activate X(=Y)–Z type bonds in amides, amidines, and carboxylate and phosphate esters, among many others that we term “generalized esters”. A Brønsted-Evans–Polanyi relationship is identified correlating the stability of the transition and final states of the X–Z generalized ester bond scission. A simple descriptor (ΣΔχ) based on the electronegativity of the atoms that constitute the bond (X, Y, Z) versus those of the catalytic site (O, Ce, Ce) captures the trend in the stability of the transition state of generalized ester bond scission and suggests a direction for modifying ceria for targeting specific organic substrates.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS); Louisiana State Univ., Baton Rouge, LA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF); National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 2470071

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 16 Vol. 12; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (108)

A Standard Solid State Pseudopotentials (SSSP) library optimized for precision and efficiency Gianluca, Prandini,; Antimo, Marrazzo,; E., Castelli, Ivano Materials Cloud https://doi.org/10.24435/materialscloud:rz-77	dataset	January 2021
Catalytic Hydrolysis of Peptides by Cerium(IV) Takarada, Tohru; Yashiro, Morio; Komiyama, Makoto Chemistry – A European Journal, Vol. 6, Issue 21 https://doi.org/10.1002/1521-3765(20001103)6:21<3906::AID-CHEM3906>3.0.CO;2-J	journal	October 2000
First-Principles Design of Highly Active and Selective Catalysts for Phosgene-Free Synthesis of Aromatic Polyurethanes Laursen, Siris; Combita, Diego; Hungría, Ana B. Angewandte Chemie International Edition, Vol. 51, Issue 17 https://doi.org/10.1002/anie.201108849	journal	March 2012
Zinc-Catalyzed Amide Cleavage and Esterification of β-Hydroxyethylamides Kita, Yusuke; Nishii, Yuji; Higuchi, Takafumi Angewandte Chemie International Edition, Vol. 51, Issue 23 https://doi.org/10.1002/anie.201201789	journal	April 2012
Über die Hydrolyse von Dipeptiden in Anwesenheit von Lanthan‐, Cer(III)‐ und Cer(IV)‐Ionen Bamann, Eugen; Trapmann, Heinz; Rother, Ana Chemische Berichte, Vol. 91, Issue 8 https://doi.org/10.1002/cber.19580910825	journal	August 1958
Esterification of Tertiary Amides by Alcohols Through C−N Bond Cleavage over CeO ₂ Toyao, Takashi; Nurnobi Rashed, Md.; Morita, Yoshitsugu ChemCatChem, Vol. 11, Issue 1 https://doi.org/10.1002/cctc.201801098	journal	August 2018
Polyoxometalates as a Novel Class of Artificial Proteases: Selective Hydrolysis of Lysozyme under Physiological pH and Temperature Promoted by a Cerium(IV) Keggin-Type Polyoxometalate Stroobants, Karen; Moelants, Eva; Ly, Hong Giang T. Chemistry - A European Journal, Vol. 19, Issue 8 https://doi.org/10.1002/chem.201203020	journal	January 2013
A Mechanistic Study of the Spontaneous Hydrolysis of Glycylserine as the Simplest Model for Protein Self‐Cleavage Mihaylov, Tzvetan T.; Parac‐Vogt, Tatjana N.; Pierloot, Kristine Chemistry – A European Journal, Vol. 20, Issue 2 https://doi.org/10.1002/chem.201303564	journal	December 2013
Direct Phenolysis Reactions of Unactivated Amides into Phenolic Esters Promoted by a Heterogeneous CeO₂ Catalyst Rashed, Md. Nurnobi; Siddiki, S. M. A. Hakim; Touchy, Abeda Sultana Chemistry – A European Journal, Vol. 25, Issue 45 https://doi.org/10.1002/chem.201901446	journal	July 2019
Shape-Controlled Ceria-based Nanostructures for Catalysis Applications Qiao, Zhen-An; Wu, Zili; Dai, Sheng ChemSusChem, Vol. 6, Issue 10 https://doi.org/10.1002/cssc.201300428	journal	September 2013
Tuning the Selectivity and Reactivity of Metal-Substituted Polyoxometalates as Artificial Proteases by Varying the Nature of the Embedded Lewis Acid Metal Ion: Tuning the Selectivity and Reactivity of Metal-Substituted Polyoxometalates as Artificial Proteases by Varying the Nature of the Embedded Lewis Acid M Sap, Annelies; Van Tichelen, Leentje; Mortier, Anneleen European Journal of Inorganic Chemistry, Vol. 2016, Issue 32 https://doi.org/10.1002/ejic.201601098	journal	October 2016
Kinetics of alkaline hydrolysis of organic esters and amides in neutrally-buffered solution Robinson, Bruce A.; Tester, Jefferson W. International Journal of Chemical Kinetics, Vol. 22, Issue 5 https://doi.org/10.1002/kin.550220502	journal	May 1990
On the origin of the catalytic power of carboxypeptidase A and other metalloenzymes Kilshtain, Alexandra Vardi; Warshel, Arieh Proteins: Structure, Function, and Bioinformatics, Vol. 77, Issue 3 https://doi.org/10.1002/prot.22466	journal	May 2009
Universality in Heterogeneous Catalysis Nørskov, J. K.; Bligaard, T.; Logadottir, A. Journal of Catalysis, Vol. 209, Issue 2 https://doi.org/10.1006/jcat.2002.3615	journal	July 2002
Metallkatalytische L�sung der Peptidbindung Bamann, Eugen; Rother, Ana; Trapmann, Heinz Die Naturwissenschaften, Vol. 43, Issue 14 https://doi.org/10.1007/BF00629390	journal	January 1956
Copper(II)-cis,cis-1,3,5-triaminocyclohexane complex-promoted hydrolysis of dipeptides: kinetic, speciation and structural studies Fujii, Yuki; Kiss, Tamas; Gajda, Tamas JBIC Journal of Biological Inorganic Chemistry, Vol. 7, Issue 7-8 https://doi.org/10.1007/s00775-002-0368-9	journal	September 2002
New chelating ligands for Co(III)-based peptide-cleaving catalysts selective for pathogenic proteins of amyloidoses Chei, Woo Suk; Ju, Heeyeon; Suh, Junghun JBIC Journal of Biological Inorganic Chemistry, Vol. 16, Issue 3 https://doi.org/10.1007/s00775-010-0750-y	journal	December 2010
Variations in Reactivity on Different Crystallographic Orientations of Cerium Oxide Mullins, David R.; Albrecht, Peter M.; Calaza, Florencia Topics in Catalysis, Vol. 56, Issue 15-17 https://doi.org/10.1007/s11244-013-0146-7	journal	July 2013
Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Kresse, G.; Furthmüller, J. Computational Materials Science, Vol. 6, Issue 1, p. 15-50 https://doi.org/10.1016/0927-0256(96)00008-0	journal	July 1996
Reactivity descriptors for ceria in catalysis Capdevila-Cortada, Marçal; Vilé, Gianvito; Teschner, Detre Applied Catalysis B: Environmental, Vol. 197 https://doi.org/10.1016/j.apcatb.2016.02.035	journal	November 2016
Adsorption structure of adenine on cerium oxide Bercha, Sofiia; Bhasker-Ranganath, Suman; Zheng, Xiaohui Applied Surface Science, Vol. 530 https://doi.org/10.1016/j.apsusc.2020.147257	journal	November 2020
Effect of Pd surface structure on the activation of methyl acetate Xu, Lijun; Xu, Ye Catalysis Today, Vol. 165, Issue 1 https://doi.org/10.1016/j.cattod.2010.12.021	journal	May 2011
Reactivity and reaction intermediates for acetic acid adsorbed on CeO2(1 1 1) Calaza, Florencia C.; Chen, Tsung-Liang; Mullins, David R. Catalysis Today, Vol. 253 https://doi.org/10.1016/j.cattod.2015.03.033	journal	September 2015
Combined theoretical and experimental study on alcoholysis of amides on CeO2 surface: A catalytic interplay between Lewis acid and base sites Kamachi, Takashi; Siddiki, S. M. A. Hakim; Morita, Yoshitsugu Catalysis Today, Vol. 303 https://doi.org/10.1016/j.cattod.2017.09.006	journal	April 2018
Theoretical investigation of dephosphorylation of phosphate monoesters on CeO2(111) Zhao, Chuanlin; Xu, Ye Catalysis Today, Vol. 312 https://doi.org/10.1016/j.cattod.2018.02.033	journal	August 2018
Metal assisted peptide bond hydrolysis: Chemistry, biotechnology and toxicological implications Wezynfeld, Nina E.; Frączyk, Tomasz; Bal, Wojciech Coordination Chemistry Reviews, Vol. 327-328 https://doi.org/10.1016/j.ccr.2016.02.009	journal	November 2016
Bulk modulus of CeO2 and PrO2—An experimental and theoretical study Gerward, L.; Staun Olsen, J.; Petit, L. Journal of Alloys and Compounds, Vol. 400, Issue 1-2 https://doi.org/10.1016/j.jallcom.2005.04.008	journal	September 2005
On the structure dependence of CO oxidation over CeO2 nanocrystals with well-defined surface planes Wu, Zili; Li, Meijun; Overbury, Steven H. Journal of Catalysis, Vol. 285, Issue 1 https://doi.org/10.1016/j.jcat.2011.09.011	journal	January 2012
Surface structure dependence of selective oxidation of ethanol on faceted CeO2 nanocrystals Li, Meijun; Wu, Zili; Overbury, S. H. Journal of Catalysis, Vol. 306 https://doi.org/10.1016/j.jcat.2013.06.019	journal	October 2013
Hydrolysis of transferrin promoted by a cerium(IV)-Keggin polyoxometalate Moons, Jens; Van Rompuy, Laura S.; Rodriguez, Alvaro Polyhedron, Vol. 170 https://doi.org/10.1016/j.poly.2019.06.010	journal	September 2019
The electronic structure of oxygen vacancy defects at the low index surfaces of ceria Nolan, Michael; Parker, Stephen C.; Watson, Graeme W. Surface Science, Vol. 595, Issue 1-3 https://doi.org/10.1016/j.susc.2005.08.015	journal	December 2005
Theoretical analysis of the adsorption of phosphoric acid and model phosphate monoesters on CeO2(111) Bhasker-Ranganath, Suman; Zhao, Chuanlin; Xu, Ye Surface Science, Vol. 705 https://doi.org/10.1016/j.susc.2020.121776	journal	March 2021
Powder diffraction analysis of cerium dioxide at high pressure Gerward, L.; Olsen, J. Staun Powder Diffraction, Vol. 8, Issue 2 https://doi.org/10.1017/S0885715600017966	journal	June 1993
Adsorbate Pairing on Oxide Surfaces: Influence on Reactivity and Dependence on Oxide, Adsorbate Pair, and Density Functional Van den Bossche, Maxime; Grönbeck, Henrik The Journal of Physical Chemistry C, Vol. 121, Issue 15 https://doi.org/10.1021/acs.jpcc.6b12789	journal	April 2017
Methyl Formate Formation during Methanol Conversion over the (111) Ceria Surface Beste, Ariana; Overbury, Steven H. The Journal of Physical Chemistry C, Vol. 121, Issue 18 https://doi.org/10.1021/acs.jpcc.7b01431	journal	May 2017
Role of the Band Gap for the Interaction Energy of Coadsorbed Fragments Castelli, Ivano E.; Man, Isabela-Costinela; Soriga, Stefan-Gabriel The Journal of Physical Chemistry C, Vol. 121, Issue 34 https://doi.org/10.1021/acs.jpcc.7b04974	journal	August 2017
Theoretical Investigation of the Structural Stabilities of Ceria Surfaces and Supported Metal Nanocluster in Vapor and Aqueous Phases Ren, Zhibo; Liu, Ning; Chen, Biaohua The Journal of Physical Chemistry C, Vol. 122, Issue 9 https://doi.org/10.1021/acs.jpcc.7b10208	journal	January 2018
Understanding Dimethyl Methylphosphonate Adsorption and Decomposition on Mesoporous CeO₂ Li, Tianyu; Tsyshevsky, Roman; Algrim, Lucas ACS Applied Materials & Interfaces, Vol. 13, Issue 45 https://doi.org/10.1021/acsami.1c16668	journal	November 2021
Elucidating the Mechanism of Ambient-Temperature Aldol Condensation of Acetaldehyde on Ceria Bhasker-Ranganath, Suman; Rahman, Md. Saeedur; Zhao, Chuanlin ACS Catalysis, Vol. 11, Issue 14 https://doi.org/10.1021/acscatal.1c01216	journal	June 2021
Catalytic Dephosphorylation Using Ceria Nanocrystals Manto, Michael J.; Xie, Pengfei; Wang, Chao ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b03472	journal	February 2017
Ceria Catalysts at Nanoscale: How Do Crystal Shapes Shape Catalysis? Trovarelli, Alessandro; Llorca, Jordi ACS Catalysis, Vol. 7, Issue 7 https://doi.org/10.1021/acscatal.7b01246	journal	June 2017
Mechanistic Insights into the Ceria-Catalyzed Synthesis of Carbamates as Polyurethane Precursors Puértolas, Begoña; Rellán-Piñeiro, Marcos; Núñez-Rico, José Luis ACS Catalysis, Vol. 9, Issue 9 https://doi.org/10.1021/acscatal.9b02086	journal	July 2019
Model studies of metalloenzymes involving metal ions as Lewis acid catalysts Suh, Junghun Accounts of Chemical Research, Vol. 25, Issue 7 https://doi.org/10.1021/ar00019a001	journal	July 1992
Carboxypeptidase A Christianson, David W.; Lipscomb, William N. Accounts of Chemical Research, Vol. 22, Issue 2 https://doi.org/10.1021/ar00158a003	journal	February 1989
Catalytic Mechanism and Three-Dimensional Structure of Adenine Deaminase ^, Kamat, Siddhesh S.; Bagaria, Ashima; Kumaran, Desigan Biochemistry, Vol. 50, Issue 11 https://doi.org/10.1021/bi101788n	journal	March 2011
Oxygen Defects and Surface Chemistry of Ceria: Quantum Chemical Studies Compared to Experiment Paier, Joachim; Penschke, Christopher; Sauer, Joachim Chemical Reviews, Vol. 113, Issue 6 https://doi.org/10.1021/cr3004949	journal	December 2012
Mechanisms of Catalysis of Nucleophilic Reactions of Carboxylic Acid Derivatives. Bender, Myron L. Chemical Reviews, Vol. 60, Issue 1 https://doi.org/10.1021/cr60203a005	journal	February 1960
Insights into the Ceria-Catalyzed Ketonization Reaction for Biofuels Applications Snell, Ryan W.; Shanks, Brent H. ACS Catalysis, Vol. 3, Issue 4 https://doi.org/10.1021/cs400003n	journal	February 2013
Toward artificial metallopeptidases: mechanisms by which platinum(II) and palladium(II) complexes promote selective, fast hydrolysis of unactivated amide bonds in peptides Zhu, Longgen; Kostic, Nenad M. Inorganic Chemistry, Vol. 31, Issue 19 https://doi.org/10.1021/ic00045a026	journal	September 1992
Hydrolysis of Unactivated Peptide Bonds by a Macrocyclic Copper(II) Complex: Cu([9]aneN3)Cl2 Hydrolyzes Both Dipeptides and Proteins Hegg, Eric L.; Burstyn, Judith N. Journal of the American Chemical Society, Vol. 117, Issue 26 https://doi.org/10.1021/ja00131a030	journal	July 1995
Metal ion catalysis of amide hydrolysis Sayre, Lawrence M. Journal of the American Chemical Society, Vol. 108, Issue 7 https://doi.org/10.1021/ja00267a037	journal	April 1986
Alkaline hydrolysis of p-nitroacetanilide and p-formylacetanilide Bender, Myron L.; Pollack, Ralph M. Journal of the American Chemical Society, Vol. 92, Issue 24 https://doi.org/10.1021/ja00727a029	journal	December 1970
“Amide Resonance” Correlates with a Breadth of C−N Rotation Barriers Kemnitz, Carl R.; Loewen, Mark J. Journal of the American Chemical Society, Vol. 129, Issue 9 https://doi.org/10.1021/ja0663024	journal	February 2007
Oxygen Vacancy-Assisted Coupling and Enolization of Acetaldehyde on CeO ₂ (111) Calaza, Florencia C.; Xu, Ye; Mullins, David R. Journal of the American Chemical Society, Vol. 134, Issue 43 https://doi.org/10.1021/ja3074243	journal	October 2012
New Selectivity and Turnover in Peptide Hydrolysis by Metal Complexes. A Palladium(II) Aqua Complex Catalyzes Cleavage of Peptides Next to the Histidine Residue Parac, Tatjana N.; Kostić, Nenad M. Journal of the American Chemical Society, Vol. 118, Issue 1 https://doi.org/10.1021/ja952162e	journal	January 1996
Rates of Uncatalyzed Peptide Bond Hydrolysis in Neutral Solution and the Transition State Affinities of Proteases Radzicka, Anna; Wolfenden, Richard Journal of the American Chemical Society, Vol. 118, Issue 26 https://doi.org/10.1021/ja954077c	journal	January 1996
The pH-Rate Profile for the Hydrolysis of a Peptide Bond Smith, Robert M.; Hansen, David E. Journal of the American Chemical Society, Vol. 120, Issue 35 https://doi.org/10.1021/ja9804565	journal	September 1998
Theoretical Study of Base-Catalyzed Amide Hydrolysis: Gas- and Aqueous-Phase Hydrolysis of Formamide Bakowies, Dirk; Kollman, Peter A. Journal of the American Chemical Society, Vol. 121, Issue 24 https://doi.org/10.1021/ja9837349	journal	June 1999
Hydrolysis of formamide at 80.degree.C and pH 1-9 Hine, Jack; King, Richard S. M.; Midden, W. Robert The Journal of Organic Chemistry, Vol. 46, Issue 16 https://doi.org/10.1021/jo00329a007	journal	July 1981
Dramatic Cooperative Effects in Adsorption of NO _x on MgO(001) Schneider, William F.; Hass, Kenneth C.; Miletic, Marina The Journal of Physical Chemistry B, Vol. 106, Issue 30 https://doi.org/10.1021/jp0257496	journal	August 2002
Insight into the Adsorption of Water on the Clean CeO ₂ (111) Surface with van der Waals and Hybrid Density Functionals Fernández-Torre, Delia; Kośmider, Krzysztof; Carrasco, Javier The Journal of Physical Chemistry C, Vol. 116, Issue 25 https://doi.org/10.1021/jp212605g	journal	June 2012
Water Adsorption and Its Effect on the Stability of Low Index Stoichiometric and Reduced Surfaces of Ceria Molinari, Marco; Parker, Stephen C.; Sayle, Dean C. The Journal of Physical Chemistry C, Vol. 116, Issue 12 https://doi.org/10.1021/jp300576b	journal	March 2012
Kinetics and Thermodynamics of H ₂ O Dissociation on Reduced CeO ₂ (111) Hansen, Heine A.; Wolverton, Christopher The Journal of Physical Chemistry C, Vol. 118, Issue 47 https://doi.org/10.1021/jp508666c	journal	November 2014
CO Adsorption and Oxidation on Ceria Surfaces from DFT+U Calculations Huang, Min; Fabris, Stefano The Journal of Physical Chemistry C, Vol. 112, Issue 23 https://doi.org/10.1021/jp709898r	journal	May 2008
Langevin Dipoles Model for ab Initio Calculations of Chemical Processes in Solution: Parametrization and Application to Hydration Free Energies of Neutral and Ionic Solutes and Conformational Analysis in Aqueous Solution Florián, Jan; Warshel, Arieh The Journal of Physical Chemistry B, Vol. 101, Issue 28 https://doi.org/10.1021/jp9705075	journal	July 1997
Calculations of Hydration Entropies of Hydrophobic, Polar, and Ionic Solutes in the Framework of the Langevin Dipoles Solvation Model Florián, Jan; Warshel, Arieh The Journal of Physical Chemistry B, Vol. 103, Issue 46 https://doi.org/10.1021/jp992041r	journal	November 1999
Surface Reactions of Acetone on Al ₂ O ₃ , TiO ₂ , ZrO ₂ , and CeO ₂ : IR Spectroscopic Assessment of Impacts of the Surface Acid−Base Properties Zaki, M. I.; Hasan, M. A.; Pasupulety, L. Langmuir, Vol. 17, Issue 3 https://doi.org/10.1021/la000976p	journal	February 2001
Cerium(IV)–cyclodextrin complex for peptide hydrolysis in neutral homogeneous solutions Yashiro, Morio; Takarada, Tohru; Miyama, Sachiko J. Chem. Soc., Chem. Commun., Issue 15 https://doi.org/10.1039/C39940001757	journal	January 1994
Morphology-dependent surface chemistry and catalysis of CeO ₂ nanocrystals Huang, Weixin; Gao, Yuxian Catal. Sci. Technol., Vol. 4, Issue 11 https://doi.org/10.1039/C4CY00679H	journal	January 2014
Versatile and sustainable alcoholysis of amides by a reusable CeO₂ catalyst Siddiki, S. M. A. Hakim; Touchy, Abeda Sultana; Tamura, Masazumi RSC Adv., Vol. 4, Issue 67 https://doi.org/10.1039/C4RA07419J	journal	January 2014
Nucleobase deaminases: a potential enzyme system for new therapies Gaded, Vandana; Anand, Ruchi RSC Advances, Vol. 8, Issue 42 https://doi.org/10.1039/C8RA04112A	journal	January 2018
Hydrolysis of amides to carboxylic acids catalyzed by Nb₂O₅ Siddiki, S. M. A. Hakim; Rashed, Md. Nurnobi; Touchy, Abeda Sultana Catalysis Science & Technology, Vol. 11, Issue 5 https://doi.org/10.1039/D0CY02230F	journal	January 2021
Metal-ion-assisted hydrolysis of dipeptides involving a serine residue in a neutral aqueous solutionElectronic supplementary information (ESI) available: Kinetic studies involving pH and concentration profiles of the rate constant. See http://www.rsc.org/suppdata/ob/b2/b209565c/ Yashiro, Morio; Sonobe, Yoko; Yamamura, Ai Organic & Biomolecular Chemistry, Vol. 1, Issue 4 https://doi.org/10.1039/b209565c	journal	January 2003
Exchange between sub-surface and surface oxygen vacancies on CeO2(111): a new surface diffusion mechanism Li, Hui-Ying; Wang, Hai-Feng; Guo, Yang-Long Chemical Communications, Vol. 47, Issue 21 https://doi.org/10.1039/c1cc11226k	journal	January 2011
Shape-controlled synthesis and catalytic application of ceria nanomaterials Zhang, Dengsong; Du, Xianjun; Shi, Liyi Dalton Transactions, Vol. 41, Issue 48 https://doi.org/10.1039/c2dt31759a	journal	January 2012
Morphology control of ceria nanocrystals for catalytic conversion of CO2 with methanol Wang, Shengping; Zhao, Lifang; Wang, Wei Nanoscale, Vol. 5, Issue 12 https://doi.org/10.1039/c3nr00831b	journal	January 2013
Acidic and basic amide hydrolysis O'Connor, Charmian Quarterly Reviews, Chemical Society, Vol. 24, Issue 4 https://doi.org/10.1039/qr9702400553	journal	January 1970
A climbing image nudged elastic band method for finding saddle points and minimum energy paths Henkelman, Graeme; Uberuaga, Blas P.; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22, p. 9901-9904 https://doi.org/10.1063/1.1329672	journal	December 2000
Efficient methods for finding transition states in chemical reactions: Comparison of improved dimer method and partitioned rational function optimization method Heyden, Andreas; Bell, Alexis T.; Keil, Frerich J. The Journal of Chemical Physics, Vol. 123, Issue 22 https://doi.org/10.1063/1.2104507	journal	December 2005
Revised self-consistent continuum solvation in electronic-structure calculations Andreussi, Oliviero; Dabo, Ismaila; Marzari, Nicola The Journal of Chemical Physics, Vol. 136, Issue 6 https://doi.org/10.1063/1.3676407	journal	February 2012
A reciprocal space based method for treating long range interactions in ab initio and force-field-based calculations in clusters Martyna, Glenn J.; Tuckerman, Mark E. The Journal of Chemical Physics, Vol. 110, Issue 6 https://doi.org/10.1063/1.477923	journal	February 1999
A dimer method for finding saddle points on high dimensional potential surfaces using only first derivatives Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 111, Issue 15 https://doi.org/10.1063/1.480097	journal	October 1999
Implicit solvation model for density-functional study of nanocrystal surfaces and reaction pathways Mathew, Kiran; Sundararaman, Ravishankar; Letchworth-Weaver, Kendra The Journal of Chemical Physics, Vol. 140, Issue 8 https://doi.org/10.1063/1.4865107	journal	February 2014
Improved initial guess for minimum energy path calculations Smidstrup, Søren; Pedersen, Andreas; Stokbro, Kurt The Journal of Chemical Physics, Vol. 140, Issue 21 https://doi.org/10.1063/1.4878664	journal	June 2014
Implicit self-consistent electrolyte model in plane-wave density-functional theory Mathew, Kiran; Kolluru, V. S. Chaitanya; Mula, Srinidhi The Journal of Chemical Physics, Vol. 151, Issue 23 https://doi.org/10.1063/1.5132354	journal	December 2019
QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials Giannozzi, Paolo; Baroni, Stefano; Bonini, Nicola Journal of Physics: Condensed Matter, Vol. 21, Issue 39, Article No. 395502 https://doi.org/10.1088/0953-8984/21/39/395502	journal	September 2009
Chemical accuracy for the van der Waals density functional Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos Journal of Physics: Condensed Matter, Vol. 22, Issue 2 https://doi.org/10.1088/0953-8984/22/2/022201	journal	December 2009
The atomic simulation environment—a Python library for working with atoms Hjorth Larsen, Ask; Jørgen Mortensen, Jens; Blomqvist, Jakob Journal of Physics: Condensed Matter, Vol. 29, Issue 27 https://doi.org/10.1088/1361-648X/aa680e	journal	June 2017
Advanced capabilities for materials modelling with Quantum ESPRESSO Giannozzi, P.; Andreussi, O.; Brumme, T. Journal of Physics: Condensed Matter, Vol. 29, Issue 46 https://doi.org/10.1088/1361-648X/aa8f79	journal	October 2017
Special points for Brillouin-zone integrations Monkhorst, Hendrik J.; Pack, James D. Physical Review B, Vol. 13, Issue 12, p. 5188-5192 https://doi.org/10.1103/PhysRevB.13.5188	journal	June 1976
Adsorbate-substrate and adsorbate-adsorbate interactions of Na and K adlayers on Al(111) Neugebauer, Jörg; Scheffler, Matthias Physical Review B, Vol. 46, Issue 24 https://doi.org/10.1103/PhysRevB.46.16067	journal	December 1992
Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation Perdew, John P.; Chevary, J. A.; Vosko, S. H. Physical Review B, Vol. 46, Issue 11 https://doi.org/10.1103/PhysRevB.46.6671	journal	September 1992
Ab initiomolecular dynamics for liquid metals Kresse, G.; Hafner, J. Physical Review B, Vol. 47, Issue 1, p. 558-561 https://doi.org/10.1103/PhysRevB.47.558	journal	January 1993
Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium Kresse, G.; Hafner, J. Physical Review B, Vol. 49, Issue 20, p. 14251-14269 https://doi.org/10.1103/PhysRevB.49.14251	journal	May 1994
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Electron-energy-loss spectra and the structural stability of nickel oxide: An LSDA+U study Dudarev, S. L.; Botton, G. A.; Savrasov, S. Y. Physical Review B, Vol. 57, Issue 3, p. 1505-1509 https://doi.org/10.1103/PhysRevB.57.1505	journal	January 1998
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
First-principles LDA + U and GGA + U study of cerium oxides: Dependence on the effective U parameter Loschen, Christoph; Carrasco, Javier; Neyman, Konstantin M. Physical Review B, Vol. 75, Issue 3 https://doi.org/10.1103/PhysRevB.75.035115	journal	January 2007
Hybrid functionals applied to rare-earth oxides: The example of ceria Da Silva, Juarez L. F.; Ganduglia-Pirovano, M. Verónica; Sauer, Joachim Physical Review B, Vol. 75, Issue 4 https://doi.org/10.1103/PhysRevB.75.045121	journal	January 2007
Van der Waals density functionals applied to solids Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos Physical Review B, Vol. 83, Issue 19 https://doi.org/10.1103/PhysRevB.83.195131	journal	May 2011
Electrostatics of solvated systems in periodic boundary conditions Andreussi, Oliviero; Marzari, Nicola Physical Review B, Vol. 90, Issue 24 https://doi.org/10.1103/PhysRevB.90.245101	journal	December 2014
Efficient Implementation of a van der Waals Density Functional: Application to Double-Wall Carbon Nanotubes Román-Pérez, Guillermo; Soler, José M. Physical Review Letters, Vol. 103, Issue 9 https://doi.org/10.1103/PhysRevLett.103.096102	journal	August 2009
Van der Waals Density Functional for General Geometries Dion, M.; Rydberg, H.; Schröder, E. Physical Review Letters, Vol. 92, Issue 24 https://doi.org/10.1103/PhysRevLett.92.246401	journal	June 2004
Scaling Properties of Adsorption Energies for Hydrogen-Containing Molecules on Transition-Metal Surfaces Abild-Pedersen, F.; Greeley, J.; Studt, F. Physical Review Letters, Vol. 99, Issue 1 https://doi.org/10.1103/PhysRevLett.99.016105	journal	July 2007
Major Advances in the Hydrolysis of Peptides and Proteins by Metal Ions and Complexes Grant, Kathryn; Kassai, Miki Current Organic Chemistry, Vol. 10, Issue 9 https://doi.org/10.2174/138527206777435535	journal	June 2006
Selectivity and Reactivity of ZrIV and CeIV Substituted Keggin Type Polyoxometalates Toward Cytochrome c in Surfactant Solutions Quanten, Thomas; De Mayaer, Tessa; Shestakova, Pavletta Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00372	journal	August 2018
Amide Bond Activation of Biological Molecules Mahesh, Sriram; Tang, Kuei-Chien; Raj, Monika Molecules, Vol. 23, Issue 10 https://doi.org/10.3390/molecules23102615	journal	October 2018

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ceria
de-esterification
deamidation
density functional theory
descriptor
enzyme mimic
generalized ester
hydrolysis

Hydrolysis of Acetamide on Low-Index CeO2 Surfaces: Ceria as a Deamidation and General De-esterification Catalyst

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Related Subjects

Hydrolysis of Acetamide on Low-Index CeO₂ Surfaces: Ceria as a Deamidation and General De-esterification Catalyst