Nucleophilic Substitution (SN 2): Dependence on Nucleophile, Leaving Group, Central Atom, Substituents, and Solvent

How Mg2+ ions lower the SN2@P barrier in enzymatic triphosphate hydrolysis

(2018) Marc A. van Bochove et al.   CHEMICAL COMMUNICATIONS

Nucleophilic Substitution in Solution: Activation Strain Analysis of Weak and Strong Solvent Effects

(2018) Trevor A. Hamlin et al.   CHEMISTRY-A EUROPEAN JOURNAL

Benchmark ab Initio Characterization of the Complex Potential Energy Surfaces of the X– + NH2Y [X, Y = F, Cl, Br, I] Reactions

(2018) Bálint Hajdu et al.   JOURNAL OF PHYSICAL CHEMISTRY A

An interacting quantum atom study of model SN 2 reactions (X- ···CH3 X, X = F, Cl, Br, and I)

(2017) Ibon Alkorta et al.   JOURNAL OF COMPUTATIONAL CHEMISTRY

Kinetics of Electrophilic Alkylations of Barbiturate and Thiobarbiturate Anions

(2017) Alexander Schade et al.   JOURNAL OF ORGANIC CHEMISTRY

Dynamics and Novel Mechanisms of SN2 Reactions on ab Initio Analytical Potential Energy Surfaces

(2017) István Szabó et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Steric Effects of Solvent Molecules on SN2 Substitution Dynamics

(2017) Xu Liu et al.   Journal of Physical Chemistry Letters

HNO Is Produced by the Reaction of NO with Thiols

(2017) Sebastian A. Suarez et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Potential energy surface stationary points and dynamics of the F− + CH3I double inversion mechanism

(2017) Yong-Tao Ma et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Eight-coordinate fluoride in a silicate double-four-ring

(2017) Maarten G. Goesten et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Nucleophilic substitution at phosphorus: stereochemistry and mechanisms

(2017) Oleg I. Kolodiazhnyi et al.   TETRAHEDRON-ASYMMETRY

Imaging dynamic fingerprints of competing E2 and SN2 reactions

(2017) Eduardo Carrascosa et al.   Nature Communications

Ion-Pair SN 2 Substitution: Activation Strain Analyses of Counter-Ion and Solvent Effects

(2016) Jalal Z. A. Laloo et al.   CHEMISTRY-A EUROPEAN JOURNAL

Dynamical Bifurcation in Gas-Phase XH− + CH3 Y SN 2 Reactions: The Role of Energy Flow and Redistribution in Avoiding the Minimum Energy Path

(2016) Yaicel G. Proenza et al.   CHEMISTRY-A EUROPEAN JOURNAL

New Insights into the Reactivity of Cisplatin with Free and Restrained Nucleophiles: Microsolvation Effects and Base Selectivity in Cisplatin-DNA Interactions

(2016) Abel de Cózar et al.   CHEMPHYSCHEM

Addition–Elimination or Nucleophilic Substitution? Understanding the Energy Profiles for the Reaction of Chalcogenolates with Dichalcogenides

(2016) Marco Bortoli et al.   Journal of Chemical Theory and Computation

Microsolvated F–(H2O) + CH3I SN2 Reaction Dynamics. Insight into the Suppressed Formation of Solvated Products

(2016) Jiaxu Zhang et al.   Journal of Physical Chemistry Letters

Ambident Reactivity of Acetyl- and Formyl-Stabilized Phosphonium Ylides

(2016) Peter A. Byrne et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Activation of the SN2 Reaction by Adjacent π Systems: The Critical Role of Electrostatic Interactions and of Dissociative Character

(2016) Raphaël Robiette et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rethinking the SN2 reaction

(2016) J. Xie et al.   SCIENCE

SN2 Reaction of IO− + CH3Cl: An Ab Initio and DFT Benchmark Study

(2015) Junxi Liang et al.   BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN

The F − + CH 3 I → FCH 3 + I − entrance channel potential energy surface

(2015) Rui Sun et al.   INTERNATIONAL JOURNAL OF MASS SPECTROMETRY

Investigation of the CH3Cl + CN− reaction in water: Multilevel quantum mechanics/molecular mechanics study

(2015) Yulong Xu et al.   JOURNAL OF CHEMICAL PHYSICS

Chemical dynamics simulations of the monohydrated OH−(H2O) + CH3I reaction. Atomic-level mechanisms and comparison with experiment

(2015) Jing Xie et al.   JOURNAL OF CHEMICAL PHYSICS

Nucleophilic Substitution in Reactions between Partially Hydrated Superoxide Anions and Alkyl Halides

(2015) Mauritz J. Ryding et al.   JOURNAL OF ORGANIC CHEMISTRY

Understanding the Reactivity and Regioselectivity of Methylation of Nitronates [R1R2CNO2]− by CH3I in the Gas Phase

(2015) Ayyaz Mahmood et al.   JOURNAL OF ORGANIC CHEMISTRY

Origin of Enhanced Reactivity of a Microsolvated Nucleophile in Ion Pair SN2 Reactions: The Cases of Sodium p-Nitrophenoxide with Halomethanes in Acetone

(2015) Qiang-Gen Li et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Double-Inversion Mechanisms of the X– + CH3Y [X,Y = F, Cl, Br, I] SN2 Reactions

(2015) István Szabó et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Influence of the leaving group on the dynamics of a gas-phase SN2 reaction

(2015) Martin Stei et al.   Nature Chemistry

Mild and Regioselective N-Alkylation of 2-Pyridones in Water

(2015) Xin Hao et al.   ORGANIC LETTERS

Comparison of direct dynamics simulations with different electronic structure methods. F− + CH3I with MP2 and DFT/B97-1

(2015) Rui Sun et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Quantum chemical investigation of the origin of activation of SN2 type halogenation by oligo-ethylene glycol—ionic liquids

(2015) Sung-Sik Lee et al.   TETRAHEDRON

Determination of the Temperature-Dependent OH− (H2O) + CH3I Rate Constant by Experiment and Simulation

(2015) Jing Xie et al.   ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS

Revealing a double-inversion mechanism for the F−+CH3Cl SN2 reaction

(2015) István Szabó et al.   Nature Communications

The activation strain model and molecular orbital theory

(2015) Lando P. Wolters et al.   Wiley Interdisciplinary Reviews-Computational Molecular Science

Covalent Hypercoordination: Can Carbon Bind Five Methyl Ligands?

(2014) William C. McKee et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

The activation strain model and molecular orbital theory: understanding and designing chemical reactions

(2014) Israel Fernández et al.   CHEMICAL SOCIETY REVIEWS

D3h [A-CE3-A]− (E = Al and Ga, A = Si, Ge, Sn, and Pb): A new class of hexatomic mono-anionic species with trigonal bipyramidal carbon

(2014) Yan-Bo Wu et al.   JOURNAL OF CHEMICAL PHYSICS

Benchmarking of Density Functionals for the Accurate Description of Thiol–Disulfide Exchange

(2014) Rui P. P. Neves et al.   Journal of Chemical Theory and Computation

How Alkyl Halide Structure Affects E2 and SN2 Reaction Barriers: E2 Reactions Are as Sensitive as SN2 Reactions

(2014) Paul R. Rablen et al.   JOURNAL OF ORGANIC CHEMISTRY

Effect of Allylic Groups on SN2 Reactivity

(2014) Ihsan Erden et al.   JOURNAL OF ORGANIC CHEMISTRY

Reaction Dynamics of Methane with F, O, Cl, and Br on ab Initio Potential Energy Surfaces

(2014) Gábor Czakó et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Do π-Conjugative Effects Facilitate SN2 Reactions?

(2014) Chia-Hua Wu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Degenerate Nucleophilic Substitution in Phosphonium Salts

(2014) Elizabeth V. Jennings et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Trinuclear Zirconium Polyhydride ({Cp*Zr(BH3CH3)}(μ-H)2{Cp*Zr(BH3CH3)}(μ-H){Cp*Zr(BH3CH3)})(μ-κ2C,H:κ1C:κ2C,H-CHBH3) and Its Derivatives: Compounds Containing a Pentacoordinated Carbon Atom

(2014) Fu-Chen Liu et al.   ORGANOMETALLICS

A multilayered-representation, quantum mechanical/molecular mechanics study of the CH3Cl + F− reaction in aqueous solution: the reaction mechanism, solvent effects and potential of mean force

(2014) Jingxue Zhang et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Understanding E2 versus SN2 Competition under Acidic and Basic Conditions

(2014) Lando P. Wolters et al.   ChemistryOpen

Cysteine-Mediated Redox Signaling: Chemistry, Biology, and Tools for Discovery

(2013) Candice E. Paulsen et al.   CHEMICAL REVIEWS

The α-effect exhibited in gas-phase SN2@N and SN2@C reactions

(2013) Yi Ren et al.   JOURNAL OF COMPUTATIONAL CHEMISTRY

Dissection of Activation Parameters in the Bell-Shaped α-Effect Following Solvent Modulation (DMSO–H2O Media)

(2013) Ik-Hwan Um et al.   JOURNAL OF ORGANIC CHEMISTRY

Direct Dynamics Simulations of the Product Channels and Atomistic Mechanisms for the OH– + CH3I Reaction. Comparison with Experiment

(2013) Jing Xie et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Investigating the α-Effect in Gas-Phase SN2 Reactions of Microsolvated Anions

(2013) Ditte L. Thomsen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Benchmark Study on the Smallest Bimolecular Nucleophilic Substitution Reaction: H−+CH4 →CH4+H−

(2013) Marcel Swart et al.   MOLECULES

The Janus-faced role of external forces in mechanochemical disulfide bond cleavage

(2013) Przemyslaw Dopieralski et al.   Nature Chemistry

Dynamics of the F− + CH3Cl → Cl− + CH3F SN2 reaction on a chemically accurate potential energy surface

(2013) István Szabó et al.   Chemical Science

Mechanism of Thiolate-Disulfide Exchange: Addition–Elimination or Effectively SN2? Effect of a Shallow Intermediate in Gas-Phase Direct Dynamics Simulations

(2012) Manikandan Paranjothy et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Chemical Dynamics Simulations of X– + CH3Y → XCH3 + Y– Gas-Phase SN2 Nucleophilic Substitution Reactions. Nonstatistical Dynamics and Nontraditional Reaction Mechanisms

(2012) Paranjothy Manikandan et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Reactions of CH3SH and CH3SSCH3 with Gas-Phase Hydrated Radical Anions (H2O)n•–, CO2•–(H2O)n, and O2•–(H2O)n

(2012) Robert F. Höckendorf et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Watching DNA polymerase η make a phosphodiester bond

(2012) Teruya Nakamura et al.   NATURE

Single solvent molecules can affect the dynamics of substitution reactions

(2012) R. Otto et al.   Nature Chemistry

Neutral Metal Atoms Acting as a Leaving Group in Gas-Phase SN2 Reactions: M(CH3)+ + NH3 → CH3NH3+ + M (M = Zn, Cd, Hg)

(2012) Robert Kretschmer et al.   ORGANOMETALLICS

Efficient and Selective Gas-Phase Monomethylation versus NH Bond Activation of Ammonia by “Bare” Zn(CH3)+: Atomic Zinc as a Leaving Group in an SN2 Reaction

(2011) Robert Kretschmer et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nucleophilic Reactivities of the Anions of Nucleobases and Their Subunits

(2011) Martin Breugst et al.   CHEMISTRY-A EUROPEAN JOURNAL

Computational Study on the Reaction Pathway of α-Bromoacetophenones with Hydroxide Ion: Possible Path Bifurcation in the Addition/Substitution Mechanism

(2011) Shuhei Itoh et al.   JOURNAL OF ORGANIC CHEMISTRY

Experimental Validation of the α-Effect in the Gas Phase

(2011) John M. Garver et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Comment on “The Interplay between Steric and Electronic Effects in SN2 Reactions”

(2010) Willem-Jan van Zeist et al.   CHEMISTRY-A EUROPEAN JOURNAL

Response to the Comment on “The Interplay between Steric and Electronic Effects in SN2 Reactions”

(2010) Israel Fernández et al.   CHEMISTRY-A EUROPEAN JOURNAL

Density Functional Calculations of E2 and SN2 Reactions: Effects of the Choice of Method, Algorithm, and Numerical Accuracy

(2010) Marcel Swart et al.   Journal of Chemical Theory and Computation

Single Electron Transfer and SN2 Reactions: The Importance of Ionization Potential of Nucleophiles

(2010) Ronald R. Sauers   Journal of Chemical Theory and Computation

E2 and SN2 Reactions of X−+ CH3CH2X (X = F, Cl); anab Initioand DFT Benchmark Study

(2010) A. Patrícia Bento et al.   Journal of Chemical Theory and Computation

Density Functional Calculations of E2 and SN2 Reactions: Effects of the Choice of Density Functional, Basis Set, and Self-Consistent Iterations

(2010) Yan Zhao et al.   Journal of Chemical Theory and Computation

Computational Investigation of the Reaction Mechanisms of Nitroxyl and Thiols

(2010) Matthew P. Sherman et al.   JOURNAL OF ORGANIC CHEMISTRY

The Mechanism of Nucleophilic Displacements at Phosphorus in Chloro-Substituted Methylphosphonate Esters: P−O vs P−C Bond Cleavage: A DFT Study

(2010) Nissan Ashkenazi et al.   JOURNAL OF ORGANIC CHEMISTRY

Pitfalls in Assessing the α-Effect: Reactions of Substituted Phenyl Methanesulfonates with HOO−, OH−, and Substituted Phenoxides in H2O

(2010) Ik-Hwan Um et al.   JOURNAL OF ORGANIC CHEMISTRY

Enhanced Reactivity of RC≡CZ−(R = H and Cl; Z = O, S, and Se) and the Influence of Leaving Group on the α-Effect in the E2 Reactions

(2010) Xi-Guang Wei et al.   JOURNAL OF ORGANIC CHEMISTRY

Gas-Phase Nucleophilic and Elimination Reactions in Simple Alkyl Nitrates

(2010) Thiago C. Correra et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Electronic Structure Theory Study of the F−+ CH3I → FCH3+ I−Potential Energy Surface†

(2010) Jiaxu Zhang et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Steric, Quantum, and Electrostatic Effects on SN2 Reaction Barriers in Gas Phase

(2010) Shubin Liu et al.   JOURNAL OF PHYSICAL CHEMISTRY A

A Direct Comparison of Reactivity and Mechanism in the Gas Phase and in Solution

(2010) John M. Garver et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ambident Reactivities of Pyridone Anions

(2010) Martin Breugst et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

C(CN)5–: transition state or intermediate?

(2010) F. Matthias Bickelhaupt et al.   MENDELEEV COMMUNICATIONS

The activation strain model of chemical reactivity

(2010) Willem-Jan van Zeist et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Hypervalent Carbon Atom: “Freezing” the SN2 Transition State

(2009) Simon C. A. H. Pierrefixe et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Mechanisms of DNA Polymerases

(2009) Anthony J. Berdis   CHEMICAL REVIEWS

The Interplay between Steric and Electronic Effects in SN2 Reactions

(2009) Israel Fernández et al.   CHEMISTRY-A EUROPEAN JOURNAL

The kinetics and mechanisms of organic reactions in liquid ammonia

(2009) Pengju Ji et al.   FARADAY DISCUSSIONS

Rotational effects in complex-forming bimolecular substitution reactions: A quantum-mechanical approach

(2009) Carsten Hennig et al.   JOURNAL OF CHEMICAL PHYSICS

Exploring the Reactivity Trends in the E2 and SN2 Reactions of X−+ CH3CH2Cl (X = F, Cl, Br, HO, HS, HSe, NH2PH2, AsH2, CH3, SiH3, and GeH3)

(2009) Xiao-Peng Wu et al.   Journal of Chemical Theory and Computation

Mechanism of SH2 Reactions of Disulfides: Frontside vs Backside, Stepwise vs Concerted

(2009) Elizabeth H. Krenske et al.   JOURNAL OF ORGANIC CHEMISTRY

Effects of Substituent and Leaving Group on the Gas-Phase SN2 Reactions of Phenoxides with Halomethanes: A DFT Investigation

(2009) Qiang-gen Li et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Theoretical Studies of the Nucleophilic Substitution of Halides and Amine at a Sulfonyl Center

(2009) Dae Dong Sung et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Steric and Solvation Effects in Ionic SN2 Reactions

(2009) Xin Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Can One Predict Changes from SN1 to SN2 Mechanisms?

(2009) Thanh Binh Phan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Reactions of α-Nucleophiles with Alkyl Chlorides: Competition between SN2 and E2 Mechanisms and the Gas-Phase α-Effect

(2009) Stephanie M. Villano et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Force-activated reactivity switch in a bimolecular chemical reaction

(2009) Sergi Garcia-Manyes et al.   Nature Chemistry

Solvolysis process of organophosphorus compound P-[2-(dimethylamino)ethyl]-N,N-dimethylphosphonamidic fluoride with simple and α-nucleophiles: a DFT study

(2009) Manoj K. Kesharwani et al.   THEORETICAL CHEMISTRY ACCOUNTS

Hypervalent versus Nonhypervalent Carbon in Noble-Gas Complexes

(2008) Simon C. A. H. Pierrefixe et al.   CHEMISTRY-A EUROPEAN JOURNAL

Frontside versus Backside SN2 Substitution at Group 14 Atoms: Origin of Reaction Barriers and Reasons for Their Absence

(2008) A. Patrícia Bento et al.   Chemistry-An Asian Journal

E2 and SN2 Reactions of X−+ CH3CH2X (X = F, Cl); anab Initioand DFT Benchmark Study

(2008) A. Patrícia Bento et al.   Journal of Chemical Theory and Computation

Perspective on Diabatic Models of Chemical Reactivity as Illustrated by the Gas-Phase SN2 Reaction of Acetate Ion with 1,2-Dichloroethane

(2008) Rosendo Valero et al.   Journal of Chemical Theory and Computation

Role of the variable active site residues in the function of thioredoxin family oxidoreductases

(2008) Alexandra T. P. Carvalho et al.   JOURNAL OF COMPUTATIONAL CHEMISTRY

Dramatic Effects of Halogen Substitution and Solvent on the Rates and Mechanisms of Nucleophilic Substitution Reactions of Aziridines

(2008) Harold D. Banks   JOURNAL OF ORGANIC CHEMISTRY

Nucleophilicity and Leaving-Group Ability in Frontside and Backside SN2 Reactions

(2008) A. Patrícia Bento et al.   JOURNAL OF ORGANIC CHEMISTRY

Determining the Transition-State Structure for Different SN2 Reactions Using Experimental Nucleophile Carbon and Secondary α-Deuterium Kinetic Isotope Effects and Theory

(2008) Kenneth C. Westaway et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Quantum Chemical Calculations of the Cl−+ CH3I → CH3Cl + I−Potential Energy Surface†

(2008) Jiaxu Zhang et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Mechanism of Thioredoxin-Catalyzed Disulfide Reduction. Activation of the Buried Thiol and Role of the Variable Active-Site Residues

(2008) Alexandra T. P. Carvalho et al.   JOURNAL OF PHYSICAL CHEMISTRY B

Hydrogen Bonding Lowers Intrinsic Nucleophilicity of Solvated Nucleophiles

(2008) Xin Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthesis and Structure of a Hexacoordinate Carbon Compound

(2008) Torahiko Yamaguchi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Origin of the SN2 Benzylic Effect

(2008) Boris Galabov et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Theory of 1,3-Dipolar Cycloadditions: Distortion/Interaction and Frontier Molecular Orbital Models

(2008) Daniel H. Ess et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The Diels−Alder Reaction on Endohedral Y3N@C78: The Importance of the Fullerene Strain Energy

(2008) Sílvia Osuna et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Reactions of the hydroperoxide anion with dimethyl methylphosphonate in an ion trap mass spectrometer: evidence for a gas phase α-effect

(2008) Andrew Michael McAnoy et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Transition States of Strain-Promoted Metal-Free Click Chemistry:  1,3-Dipolar Cycloadditions of Phenyl Azide and Cyclooctynes

(2008) Daniel H. Ess et al.   ORGANIC LETTERS

Stepwise walden inversion in nucleophilic substitution at phosphorus

(2008) Marc A. van Bochove et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Imaging Nucleophilic Substitution Dynamics

(2008) J. Mikosch et al.   SCIENCE

Hypervalent Silicon versus Carbon: Ball-in-a-Box Model

(2007) Simon C. A. H. Pierrefixe et al.   CHEMISTRY-A EUROPEAN JOURNAL

QUILD: QUantum-regions interconnected by local descriptions

(2007) Marcel Swart et al.   JOURNAL OF COMPUTATIONAL CHEMISTRY

Mechanism of Thiolate−Disulfide Interchange Reactions in Biochemistry

(2007) Robert D. Bach et al.   JOURNAL OF ORGANIC CHEMISTRY