Demystifying Solvent Effects on Diels–Alder Reactions in Pure and Mixed Solvents: A Combined Electronic DFT and QM/MM Study

[1]  Cuiping Li,et al.  Efficient and Reversible Capture of CO2 in CO2-Binding Organic Liquids Formed by 1,1,3,3-Tetramethylguanidine and Glycerol Derivatives , 2023, ACS Sustainable Chemistry & Engineering.

[2]  Runnan Yu,et al.  Triphenylamine-Derived Solid-State Emissive Carbon Dots for Multicolor High-Efficiency Electroluminescent Light-Emitting Diodes. , 2023, Angewandte Chemie.

[3]  H. Qian,et al.  Pd/Xu-Phos-catalyzed asymmetric elimination of fully substituted enol triflates into axially chiral trisubstituted allenes , 2023, Science advances.

[4]  Lin-wang Wang,et al.  Ion Solvation Free Energy Calculation Based on Ab Initio Molecular Dynamics Using a Hybrid Solvent Model. , 2022, Journal of chemical theory and computation.

[5]  T. Lu,et al.  Independent gradient model based on Hirshfeld partition: A new method for visual study of interactions in chemical systems , 2021, J. Comput. Chem..

[6]  Junhang Dong,et al.  Determining Dielectric Constants for Complex Solvent Mixtures by Microwave Sensing and Model Prediction. , 2021, The journal of physical chemistry. A.

[7]  B. Hartke,et al.  Improved prediction of solvation free energies by machine-learning polarizable continuum solvation model , 2021, Nature Communications.

[8]  T. Hoye,et al.  Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes. , 2021, Chemical reviews.

[9]  G. Cisneros,et al.  Development and application of quantum mechanics/molecular mechanics methods with advanced polarizable potentials , 2021, Wiley interdisciplinary reviews. Computational molecular science.

[10]  M. Brehm,et al.  Exploring Free Energy Profiles of Enantioselective Organocatalytic Aldol Reactions under Full Solvent Influence , 2020, Molecules.

[11]  Alex M. Maldonado,et al.  First-principles modeling of chemistry in mixed solvents: Where to go from here? , 2020, The Journal of chemical physics.

[12]  Z. Tong,et al.  Solvent Effects on the Symmetric and Asymmetric SN2 Reactions in Acetonitrile Solution: A Reaction Density Functional Theory Study. , 2020, The journal of physical chemistry. B.

[13]  Shuangliang Zhao,et al.  Solvent effects on a derivative of 1,3,4-oxadiazole tautomerization reaction in water: A reaction density functional theory study , 2020 .

[14]  M. Bühl,et al.  Ab Initio Molecular Dynamics Investigation of Beryllium Complexes. , 2020, Inorganic chemistry.

[15]  O. Acevedo,et al.  Accurate Diels-Alder Energies and Endo Selectivity in Ionic Liquids Using the OPLS-VSIL Force Field , 2020, International journal of molecular sciences.

[16]  P. Anastas,et al.  Designing for a green chemistry future , 2020, Science.

[17]  G. Huber,et al.  Effect of Mixed-Solvent Environments on the Selectivity of Acid-Catalyzed Dehydration Reactions , 2020 .

[18]  Ali Hussain Motagamwala,et al.  Enhanced Furfural Yields from Xylose Dehydration in the γ-Valerolactone/Water Solvent System at Elevated Temperatures. , 2018, ChemSusChem.

[19]  J. Dumesic,et al.  Solvent-enabled control of reactivity for liquid-phase reactions of biomass-derived compounds , 2018, Nature Catalysis.

[20]  Yufang Liu,et al.  Effects of solvent polarity and hydrogen bonding on coumarin 500 , 2016 .

[21]  F. Shi,et al.  Catalytic asymmetric inverse-electron-demand oxa-Diels-Alder reaction of in situ generated ortho-quinone methides with 3-methyl-2-vinylindoles. , 2015, Angewandte Chemie.

[22]  T. A. Nijhuis,et al.  Direct Synthesis of Hydrogen Peroxide over Au‐Pd Catalyst—The Effect of Co‐Solvent Addition , 2015 .

[23]  Y. Shibuta,et al.  Ab Initio Molecular Dynamics Simulation of Ethylene Reaction on Nickel (111) Surface , 2015 .

[24]  S. Aoyagi,et al.  Kinetic study of the Diels-Alder reaction of Li⁺@C₆₀ with cyclohexadiene: greatly increased reaction rate by encapsulated Li⁺. , 2014, Journal of the American Chemical Society.

[25]  Xin Yang,et al.  Medium effects on the 1,3-dipolar cycloaddition of pyridazinium dicyanomethanide with ethyl vinyl ketone in pure and mixed solvents from QM/MM simulations. , 2014, The Journal of organic chemistry.

[26]  S. Manzetti,et al.  Wavefunction and reactivity study of benzo[a]pyrene diol epoxide and its enantiomeric forms , 2014, Structural Chemistry.

[27]  C. Adjiman,et al.  Computer-aided molecular design of solvents for accelerated reaction kinetics. , 2013, Nature chemistry.

[28]  Tian Lu,et al.  Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm. , 2012, Journal of molecular graphics & modelling.

[29]  Tian Lu,et al.  Multiwfn: A multifunctional wavefunction analyzer , 2012, J. Comput. Chem..

[30]  S. Senior,et al.  Effect of acetonitrile–water mixtures on the reaction of dinitrochlorobenzene and dinitrochlorobenzotrifluoride with hydroxide ion , 2010 .

[31]  Julia Contreras-García,et al.  Revealing noncovalent interactions. , 2010, Journal of the American Chemical Society.

[32]  W. L. Jorgensen,et al.  Advances in quantum and molecular mechanical (QM/MM) simulations for organic and enzymatic reactions. , 2010, Accounts of chemical research.

[33]  Shigeyoshi Sakaki,et al.  A theoretical analysis of a Diels-Alder reaction in ionic liquids. , 2009, The journal of physical chemistry. B.

[34]  R. J. Sengwa,et al.  Dielectric behaviour and hydrogen bond molecular interaction study of formamide-dipolar solvents binary mixtures , 2009 .

[35]  R. Raghunathan,et al.  Indium chloride catalyzed intramolecular cyclization of N-aryl imines: synthesis of pyrrolo[2,3-d]pyrimidine annulated tetrahydroquinoline derivatives , 2008 .

[36]  W. L. Jorgensen,et al.  Understanding Rate Accelerations for Diels-Alder Reactions in Solution Using Enhanced QM/MM Methodology. , 2007, Journal of chemical theory and computation.

[37]  William L Jorgensen,et al.  Elucidation of Rate Variations for a Diels-Alder Reaction in Ionic Liquids from QM/MM Simulations. , 2007, Journal of chemical theory and computation.

[38]  Julian Tirado-Rives,et al.  Molecular modeling of organic and biomolecular systems using BOSS and MCPRO , 2005, J. Comput. Chem..

[39]  F. Weigend,et al.  Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. , 2005, Physical chemistry chemical physics : PCCP.

[40]  William L Jorgensen,et al.  Influence of inter- and intramolecular hydrogen bonding on kemp decarboxylations from QM/MM simulations. , 2005, Journal of the American Chemical Society.

[41]  M. Finn,et al.  "On water": unique reactivity of organic compounds in aqueous suspension. , 2005, Angewandte Chemie.

[42]  S. Itsuno Chiral polymer synthesis by means of repeated asymmetric reaction , 2005 .

[43]  William L Jorgensen,et al.  Solvent effects and mechanism for a nucleophilic aromatic substitution from QM/MM simulations. , 2004, Organic letters.

[44]  William L Jorgensen,et al.  Steric retardation of SN2 reactions in the gas phase and solution. , 2004, Journal of the American Chemical Society.

[45]  Hak-Kim Chan,et al.  A simple relationship between dielectric constant of mixed solvents with solvent composition and temperature. , 2004, International journal of pharmaceutics.

[46]  William L. Jorgensen,et al.  QM/MM Simulations for Diels−Alder Reactions in Water: Contribution of Enhanced Hydrogen Bonding at the Transition State to the Solvent Effect† , 2002 .

[47]  W. L. Jorgensen,et al.  Origin of the Inversion of the Acidity Order for Haloacetic Acids on Going from the Gas Phase to Solution , 2000 .

[48]  F. Hirata,et al.  Solvent Effects on a Diels−Alder Reaction in Supercritical Water: RISM-SCF Study , 2000 .

[49]  William L. Jorgensen,et al.  OPLS ALL-ATOM MODEL FOR AMINES : RESOLUTION OF THE AMINE HYDRATION PROBLEM , 1999 .

[50]  William L. Jorgensen,et al.  A Quantum Mechanical and Molecular Mechanical Method Based on CM1A Charges: Applications to Solvent Effects on Organic Equilibria and Reactions , 1998 .

[51]  W. L. Jorgensen,et al.  Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids , 1996 .

[52]  K Schulten,et al.  VMD: visual molecular dynamics. , 1996, Journal of molecular graphics.

[53]  J. Murray,et al.  Statistically-based interaction indices derived from molecular surface electrostatic potentials: a general interaction properties function (GIPF) , 1994 .

[54]  W. L. Jorgensen,et al.  Ab initio study of Diels-Alder reactions of cyclopentadiene with ethylene, isoprene, cyclopentadiene, acrylonitrile, and methyl vinyl ketone , 1993 .

[55]  Cheng Chang,et al.  Properties of atoms in molecules: atomic volumes , 1987 .

[56]  Eamonn F. Healy,et al.  Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model , 1985 .

[57]  W. L. Jorgensen,et al.  Comparison of simple potential functions for simulating liquid water , 1983 .

[58]  Peter Politzer,et al.  Chemical Applications of Atomic and Molecular Electrostatic Potentials: "Reactivity, Structure, Scattering, And Energetics Of Organic, Inorganic, And Biological Systems" , 2013 .