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Matthew Wodrich

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Related publications (86)

Page 3 of 5

Ping-Pong Protons: How Hydrogen Bonding Networks Facilitate Heterolytic Bond Cleavages in Peptide Radical Cations

Anne-Clémence Corminboeuf, Yury Tsybin, Matthew Wodrich, Konstantin Zhurov

Electron capture and electron transfer dissociation (ECD/ETD) tandem mass spectrometry (MS/MS) are commonly employed techniques for biomolecular analysis. The ECD/ETD process predominately cleaves N-C-alpha peptide backbone bonds, leading to primary sequen ...

Amer Chemical Soc2014

The (not so) simple prediction of enantioselectivity - a pipeline for high-fidelity computations

Anne-Clémence Corminboeuf, Matthew Wodrich, Rubén Laplaza Solanas

The computation of reaction selectivity represents an appealing complementary route to experimental studies and a powerful means to refine catalyst design strategies. Accurately establishing the selectivity of reactions facilitated by molecular catalysts, ...

ROYAL SOC CHEMISTRY2022

Quantification of "Fuzzy" Chemical Concepts: A Computational Perspective

Anne-Clémence Corminboeuf, Matthew Wodrich, Jérôme Florian Gonthier

Chemists recurrently utilize "fuzzy'' chemical concepts (e.g. atomic charges, the chemical bond, strain, aromaticity, branching, etc.), which lack unique quantitative assessments but, nonetheless, are frequently employed as tools for understanding the intr ...

Royal Society of Chemistry2012

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

Jérôme Waser, Matthew Wodrich, Paola Caramenti, Nina Declas, Romain Gaëtan Tessier

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

2019

X-Ray and NMR Structural Data of Ethynylbenziodoxolones (EBXs) Reagents and Their Analogues

Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Matthew Wodrich, Stefano Nicolai, Durga Prasada Rao Hari, Eliott Hugo Joran Le Du, Nieves Pilar Ramirez Hernandez

First synthesized in 1991, EthynylBenziodoXolones (EBXs) - cyclic hypervalent iodine reagents derived from 2-iodobenzoic acid - are now among the most versatile electrophilic alkynylation reagents. Due to their cyclic structure, these reagents exhibit enha ...

WILEY-V C H VERLAG GMBH2023

Chiral Phosphoric Acid-catalyzed Enantioselective Higher-order Cycloadditions: Temperature-dependent Periselectivity

Jieping Zhu, Matthew Wodrich

Higher-order cycloadditions (HOCs) are powerful tools for constructing complex cyclic structures, but their synthetic utility is often limited by poor periselectivity and challenges in achieving high diastereo- and enantioselectivity. Herein, we report a c ...

AMER CHEMICAL SOC2025

Donor-Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium-Catalyzed (4+2) Annulation with Indoles

Jérôme Waser, Matthew Wodrich, Emma Gabrielle Louise Robert, Vincent Géry C Pirenne

A convenient one-step synthesis of beta-aminocyclobutane monoesters starting from commercially available reagents is reported. The obtained strained rings undergo (4+2) dearomative annulation with indole partners using silylium catalysis. This organocataly ...

Wiley-VCH Verlag GmbH2023

Overcoming the Pitfalls of Computing Reaction Selectivity from Ensembles of Transition States

Anne-Clémence Corminboeuf, Matthew Wodrich, Rubén Laplaza Solanas

The prediction of reaction selectivity is a challenging task for computational chemistry, not only because many molecules adopt multiple conformations but also due to the exponential relationship between effective activation energies and rate constants. To ...

2024

Unraveling Metal/Pincer Ligand Effects in the Catalytic Hydrogenation of Carbon Dioxide to Formate

Anne-Clémence Corminboeuf, Matthew Wodrich, Boodsarin Sawatlon

The hydrogenation of carbon dioxide to formate is an intriguing reaction from both an environmental and an energy perspective, primarily due to the prospective uses of the product as a platform chemical in numerous applications such as an organic hydrogen ...

AMER CHEMICAL SOC2018

A Functional Model of [Fe]-Hydrogenase

Rosario Scopelliti, Xile Hu, Matthew Wodrich, Tao Xu, Simona Mazza

[Fe]-Hydrogenase catalyzes the hydrogenation of a biological substrate via the heterolytic splitting of molecular hydrogen. While many synthetic models of [Fe]-hydrogenase have been prepared, none yet are capable of activating H-2 on their own. Here, we re ...

American Chemical Society2016

Bimetallic Oxidative Addition Involving Radical Intermediates in Nickel-Catalyzed Alkyl-Alkyl Kumada Coupling Reactions

Xile Hu, Matthew Wodrich, Jan Breitenfeld, Jesus Ruiz

Many nickel-based catalysts have been reported for cross-coupling reactions of nonactivated alkyl halides. The mechanistic understanding of these reactions is still primitive. Here we report a mechanistic study of alkyl-alkyl Kumada coupling catalyzed by a ...

American Chemical Society2013

On the Generality of Molecular Volcano Plots

Anne-Clémence Corminboeuf, Matthew Wodrich, Boodsarin Sawatlon, Michael Markus Busch

In homogeneous catalysis, the structure and electronic config-uration of the active catalysts can vary significantly. Changes inligation, oxidation, and spin states have the potential to influ-ence the catalytic cycle energet ics strongly that, to a larged ...

Wiley-VCH Verlag2018

Reply to Comment on 'Physics-based representations for machine learning properties of chemical reactions'

Anne-Clémence Corminboeuf, Matthew Wodrich, Rubén Laplaza Solanas, Puck Elisabeth van Gerwen

Recently, we published an article in this journal that explored physics-based representations in combination with kernel models for predicting reaction properties (i.e. TS barrier heights). In an anonymous comment on our contribution, the authors argue, am ...

2023

Accessing elusive σ-type cyclopropenium cation equivalents through redox gold catalysis

Jérôme Waser, Matthew Wodrich, Xiangdong Li

Cyclopropenes are the smallest unsaturated carbocycles. Removing one substituent from cyclopropenes leads to cyclopropenium cations (C3 + systems, CPCs). Stable aromatic pi-type CPCs were discovered by Breslow in 1957 by removing a substituent on the aliph ...

2024

The atomic-resolution crystal structure of activated [Fe]-hydrogenase

Xile Hu, Matthew Wodrich

Hydrogenases are promising templates for constructing new H-2-based catalysts. [Fe]-hydrogenase, which features an ironguanylylpyridinol (FeGP) cofactor, catalyses a reversible hydride transfer from H-2 to methenyl-tetrahydromethanopterin (methenyl-H4MPT+, ...

NATURE PUBLISHING GROUP2019

Functional Models of the Nickel Pincer Nucleotide Cofactor of Lactate Racemase

Xile Hu, Farzaneh Fadaei Tirani, Matthew Wodrich, Huijie Pan, Renyi Shi

A novel nickel pincer cofactor was recently discovered in lactate racemase. Reported here are three synthetic nickel pincer complexes that are both structural and functional models of the pincer cofactor in lactate racemase. DFT computations suggest the ip ...

Wiley-VCH Verlag GmbH2019

Sequential N–O and N–N Bond Cleavage of N-Heterocyclic Carbene-Activated Nitrous Oxide with a Vanadium Complex

Rosario Scopelliti, Kay Severin, Matthew Wodrich, Euro Solari, Alexander Tskhovrebov

Chemically induced bond cleavage of nitrous oxide typically proceeds by rupture of the N–O bond with concomitant O-atom transfer and liberation of dinitrogen. On a few occasions, N–N bond scission has been observed instead. We report a reaction sequence in ...

2012

Empirical Corrections to Density Functional Theory Highlight the Importance of Nonbonded Intramolecular Interactions in Alkanes

Anne-Clémence Corminboeuf, Matthew Wodrich, Daniel Filipe Dos Santos Alves Jana

Energies of alkanes computed with many popular and even newer density functionals are flawed by systematic errors, which become considerable with larger molecules. The same energies, however, are well described by post-Hartree-Fock methods. Similar DFT sho ...

2008

Enantioselective acyl-trifluoromethylation of olefins by bulky thiazolium carbene catalysis

Nicolai Cramer, Matthew Wodrich, Sripati Jana

Enantioenriched α-chiral β-fluorinated ketones are valuable structural motifs with application in several fields. The recently emerged concept of NHC-catalyzed radical acyl-trifluoromethylation of olefins offers a rapid route to construct racemic β-fluorin ...

2025

Probing Substrate Scope with Molecular Volcanoes

Anne-Clémence Corminboeuf, Matthew Wodrich, Boodsarin Sawatlon

Molecular volcano plots, a tool generally used to identify ideal catalysts for a given chemical transformation, are employed in an alternative fashion to examine the substrate scope by revealing the range of substrates that can be accommodated by a single ...

AMER CHEMICAL SOC2020