Selected Publications

Origin of the a-Effect in SN2 Reactions

T. Hansen, P. Vermeeren, F. Matthias Bickelhaupt, T. A. Hamlin

Angew. Chem. 2021, 133; Angew. Chem. Int. Ed. 2021, 60, online


Not Carbon s–p Hybridization, but Coordination Number Determines C–H and C–C Bond Length

P. Vermeeren, W.-J. van Zeist, T. A. Hamlin, C. Fonseca Guerra, F. M. Bickelhaupt

Chem. Eur. J. 2021, 27, 7074-7079 (Cover, Highlighted in C2W Magazine)


How Metallylene Catalysts Activate Small Molecules

P. Vermeeren, M. T. Doppert, F. M. Bickelhaupt, T. A. Hamlin

Chem. Sci. 2021, 12, 4526-4536


Bifunctional Hydrogen Bond Donor-Catalyzed Diels-Alder Reactions: Origin of Selectivity and Rate Enhancement

P. Vermeeren, T. A. Hamlin, F. M. Bickelhaupt, I. Fernandez 

Chem. Eur. J. 2021, 27, 5180-5190 (Cover, Hot Paper)


How Oriented External Electric Fields Modulate Reactivity S. Yu, P. Vermeeren, T. A. Hamlin, F. M. Bickelhaupt

Chem. Eur. J. 2021, 27, 5683-5693 (Cover)


Bismuth Amides (Re-)Investigated: Mediators of Facile and Highly Selective Pn–Pn Radical Coupling Reactions (Pn = N, P, As)

K. Oberdorf, A. Hanft, J. Ramler, I. Krummenacher, F. M. Bickelhaupt, J. Poater, C. Lichtenberg

Angew. Chem. 2021, 133; Angew. Chem. Int. Ed. 2021, 60, online.


Nature and Strength of Lewis Acid/Base Interaction in Boron and Nitrogen Trihalides

D. Rodrigues Silva, L. de Azevedo Santos, M. Puggina de Freitas, C. Fonseca Guerra, T. A. Hamlin

Chem. Asian. J. 2020, 15, 4043-4054 (VIP and Cover)


A Unified Framework for Understanding Nucleophilicity and Protophilicity in the SN2/E2 Competition

P. Vermeeren, T. Hansen, P. Jansen, M. Swart, T. A. Hamlin, F. M. Bickelhaupt

Chem. Eur. J. 2020, 26, 15538-15548 (Cover, issue #1000)


The Nature of Nonclassical Carbonyl Ligands Explained by Kohn-Sham Molecular Orbital Theory S. C. C. van der Lubbe, P. Vermeeren, C. Fonseca Guerra, F. M. Bickelhaupt

Chem. Eur. J. 2020, 26, 15690-15699 (issue #1000)


Origin of Rate Enhancement and Asynchronicity in Iminium Catalyzed Diels-Alder Reactions

P. Vermeeren, T. A. Hamlin, I. Fernandez, F. M. Bickelhaupt 

Chem. Sci. 2020, 11, 8105-8112 (Cover)


Mechanism of Biomolecular Recognition of Trimethyllysine by the Fluorinated Aromatic Cage of Epigenetic Reader Proteins

B. J. G. E. Pieters, M. H. M. Wuts, J. Poater, K. Kumar, P. B. White, J. J. A. G. Kamps, W. Sherman, G. J. M. Pruijn, R. S. Paton, T. Beuming, F. M. Bickelhaupt, J. Mecinovic 

Commun. Chem. 2020, 3, 69/1-12


Probing Halogen–π versus CH–π Interactions in Molecular Balance

J. Jian, J. Poater, P. B. White, C. J. McKenzie, F. M. Bickelhaupt, J. Mecinovic

Org. Lett. 2020, 22, 7870-7873


Computationally Guided Molecular Design to Minimize the LE/CT Gap in D-π-A Fluorinated Triarylboranes for Efficient TADF via D and π-Bridge Tuning

A. Narsaria, F. Rauch, J. Krebs, P. Endres, A. Friedrich, I. Krummenacher, H. Braunschweig, M. Finze, J. Nitsch, F. M. Bickelhaupt, T. B. Marder

Adv. Funct. Mater. 2020, 30, 2002064/1-15


How Lewis Acids Catalyze Diels-Alder Reactions

P. Vermeeren, T. A. Hamlin, I. Fernandez, F. M. Bickelhaupt

Angew. Chem. 2020, 132, 6260-6265Angew. Chem. Int. Ed. 2020, 59, 6201-6206


Understanding Chemical Reactivity Using the Activation Strain Model

P. Vermeeren, S. C. C. van der Lubbe, C. Fonseca Guerra, F. M. Bickelhaupt, T. A. Hamlin

Nature Protoc. 2020, 15, 649-667


Distortion-Controlled Red-Shift of Organic Dye Molecules

A. K. Narsaria, J. Poater, C. Fonseca Guerra, A. W. Ehlers, T. A. Hamlin, K. Lammertsma, F. M. Bickelhaupt

Chem. Eur. J. 2020, 26, 2080-2093


Ambident Nucleophilic Substitution: Understanding Non-HSAB Behavior through Activation Strain and Conceptual DFT Analyses

T. Bettens, M. Alonso, F. De Proft, T. A. Hamlin, F. M. Bickelhaupt

Chem. Eur. J. 2020, 26, 3884-3893


How Dihalogens Catalyze Michael Addition Reactions

T. A. Hamlin, I. Fernandez, F. M. Bickelhaupt

Angew. Chem. 2019, 131, 9015-9020Angew. Chem. Int. Ed. 2019, 58, 8922-8926 (Highlighted in Chemistry World: “Quantum mechanical mechanism behind 100-year-old textbook reaction revealed”)


Secondary Electrostatic Interaction Model Revised: Prediction Comes Mainly from Measuring Charge Accumulation in Hydrogen-Bonded Monomers

S. C. C. van der Lubbe, F. Zaccaria, X. Sun, C. Fonseca Guerra

 J. Am. Chem. Soc. 2019 141, 4878-4885 (Cover)


Dual Activation of Aromatic Diels-Alder Reactions

A. K. Narsaria, T. A. Hamlin, K. Lammertsma, F. M. Bickelhaupt

Chem. Eur. J. 2019, 25, 9902-9912 (Cover & Hot Paper)


Structural Distortion of Cycloalkynes Influences Cycloaddition Rates both by Strain and Interaction Energies

T. A. Hamlin, B. J. Levandowski, A. K. Narsaria, K. N. Houk, F. M. Bickelhaupt

Chem. Eur. J. 2019, 25, 6342-6348 (Cover)


Understanding the Differences Between Iron and Palladium in Cross-Coupling Reactions

X. Sun, M. V. J. Rocha, T. A. Hamlin, J. Poater, F. M. Bickelhaupt

Phys. Chem. Chem. Phys. 2019, 21, 9651-9664 (Cover)


Facile Insertion of Carbon Monoxide into a Bismuth–Nitrogen Bond

J. Ramler, J. Poater, F. Hirsch, B. Ritschel, I. Fischer, F. M. Bickelhaupt, C. Lichtenberg

Chem. Sci. 2019, 10, 4169-4176


The Nature of Hydrogen Bonds: A Delineation of the Role of Different Energy Components on Hydrogen Bond Strengths and Lengths

S. C. C. van der Lubbe, C. Fonseca Guerra

Chem. Asian J. 2019, 14, 2760-2769 (Cover)


Cation Affinities throughout The Periodic Table

Z. Boughlala, C. Fonseca Guerra, F. M. Bickelhaupt

In: Advances in Inorganic Chemistry; R. van Eldik, R. Puchta, Eds.; Academic Press: San Diego, 2019, Vol. 73, Chapter 6, pp. 123-158 (Thematic volume devoted to ‘Computational Chemistry’)


Arylic C–X Bond Activation by Palladium Catalysts: Activation-Strain Analyses of Reactivity Trends

P. Vermeeren, X. Sun, F. M. Bickelhaupt

Scientific Reports 2018, 8, 10729/1-10


RNA vs DNA G-Quadruplex: The Origin of Increased Stability

F. Zaccaria, C. Fonseca Guerra

Chem. Eur. J.  2018, 24, 16315-16322 (Cover)


How Mg2+ Ions Lower the SN2@P Barrier in Enzymatic Triphosphate Hydrolysis

M. A. van Bochove, G. Roos, C. Fonseca Guerra, T. A. Hamlin, F. M. Bickelhaupt 

Chem. Commun. 2018, 54, 3448-3451 (Cover)


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

T. A. Hamlin, B. van Beek, L. P. Wolters, F. M. Bickelhaupt

Chem. Eur. J. 2018, 24, 5927-5938


Relevance of Orbital Interactions and Pauli Repulsion in the Metal-Metal Bond of Coinage Metals

M. B. Brands, J. Nitsch, C. Fonseca Guerra

Inorg. Chem 2018, 57, 2603-2608 


Double CH Activation of a Masked Cationic Bismuth Amide

B. Ritschel, J. Poater, H. Dengel, F. M. Bickelhaupt, C. Lichtenberg

Angew. Chem. 2018, 130, 3887-3891Angew. Chem. Int. Ed. 2018, 57, 3825-3829


Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model

F. M. Bickelhaupt, K. N. Houk

Angew. Chem. 2017, 129, 10204-10221 (Frontispiece & Cover); Angew. Chem. Int. Ed. 2017, 56, 10070-10086 (Frontispiece & Cover)


8-Coordinate Fluoride in a Silicate Double-4-Ring

M. G. Goesten, R. Hoffmann, F. M. Bickelhaupt, E. J. M. Hensen

Proc. Nat. Acad. Sci. 2017, 114, 828-833 (highlighted in: Science 2017, 355, 592-593)


Hydrogen bond strength of CC and GG pairs is determined by steric repulsion: electrostatics and charge transfer overruled

S. C. C. van der Lubbe, C. Fonseca Guerra

Chem. Eur. J. 2017, 23, 10249-10253 (Hot paper, Cover and cover profile)


Cesium’s Off-the-map Valence Orbital

M. G. Goesten, M. Rahm, F. M. Bickelhaupt, E. J. M. Hensen

Angew. Chem. 2017, 129, 9904-9908Angew. Chem. Int. Ed. 2017, 56, 9772-9776


Glucose-Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA

E. Vengut-Climent, I. Gomez-Pinto, R. Lucas, P. Penalver, A. Avino, C. Fonseca Guerra, F. M. Bickelhaupt, R. Eritja, C. Gonzalez, J. C. Morales

Angew. Chem. 2016, 128, 8785-8789Angew. Chem. Int. Ed. 2016, 55, 8643-8647


Six-coordinate Group-13 Complexes: Role of d Orbitals and Electron-Rich Multi-center Bonding

M. G. Goesten, C. Fonseca Guerra, F. Kapteijn, J. Gascon, F. M. Bickelhaupt

Angew. Chem. Int. Ed. 2015, 54, 12034-12038 (VIP + Cover)


Chemical Basis for the Recognition of Trimethyllysine by Epigenetic Reader Proteins

J. J. A. G. Kamps, J. Huang, J. Poater, C. Xu, B. J. G. E. Pieters, A. Dong, J. Min, W. Sherman, T. Beuming, F. M. Bickelhaupt, H. Li, J. Mecinovic

Nature Commun. 2015, 6, 8911/1-12


Role of Steric Attraction and Bite-Angle Flexibility in Metal-Mediated C–H Bond Activation

L. P. Wolters, R. Koekkoek, F. M. Bickelhaupt

ACS Catalysis 2015, 5, 5766-5775


Bite-Angle Bending as a Key for Understanding Group-10 Metal Reactivity of d10-[M(NHC)2] Complexes with Sterically Modest NHC Ligands

F. Hering, J. Nitsch, U. Paul, A. Steffen, F. M. Bickelhaupt, U. Radius

Chem. Sci. 2015, 6, 1426-1432


The Activation Strain Model & Molecular Orbital Theory

L. P. Wolters, F. M. Bickelhaupt 

WIRES Comput. Mol. Sci. 2015, 5, 324-343


Highly Accelerated Inverse Electron-Demand Cycloaddition of Electron-Deficient Azides with Aliphatic Cyclooctynes

J. Dommerholt, O. van Rooijen, A. Borrmann, C. Fonseca Guerra, F. M. Bickelhaupt, F. L. van Delft

Nature Commun. 2014, 5, 5378/1-7


d Regime, s Regime and Intrinsic Bite-Angle Flexibility: New Concepts for Designing d10-MLn Catalysts

L. P. Wolters, W. J. van Zeist, F. M. Bickelhaupt

Chem. Eur. J. 2014, 20, 11370-11381 (cover)


Activation Strain Model and Molecular Orbital Theory: Understanding and Designing Chemical Reactions of Chemical Reactivity

I. Fernandez, F. M. Bickelhaupt 

Chem. Soc. Rev. 2014, 43, 4953-4967


Stereodivergent SN2@P Reactions of Borane Oxazaphospholidines: Experimental and Theoretical Studies

H. Zijlstra, T. Leon, A. de Cozar, C. Fonseca Guerra, D. Byrom, A. Riera, X. Verdaguer, F. M. Bickelhaupt 

J. Am. Chem. Soc. 2013, 135, 4483-4491


Normal-to-Abnormal Rearrangement and NHC Activation in Three-Coordinate Iron(II) Carbene Complexes

B. M. Day, T. Pugh, D. Hendriks, C. Fonseca Guerra, D. J. Evans, F. M. Bickelhaupt, R. A. Layfield

J. Am. Chem. Soc. 2013, 135, 13338-13341


Selectivity in DNA Replication. Interplay of Steric Shape, Hydrogen Bonds, π-Stacking and Solvent Effects

J. Poater, M. Swart, C. Fonseca Guerra, F. M. Bickelhaupt 

Chem. Commun. 2011, 47, 7326-7328


Telomere Structure and Stability: Covalency in Hydrogen Bonds, Not Resonance Assistance, Causes Cooperativity in Guanine Quartets

C. Fonseca Guerra, H. Zijlstra, G. Paragi, F. M. Bickelhaupt

Chem. Eur. J. 2011, 17, 12612-12622


Catalyst Selection based on Intermediate Stability measured by Mass Spectrometry

J. Wassenaar, E. Jansen, W.-J. van Zeist, F. M. Bickelhaupt, M. A. Siegler, A. L. Spek, J. N. H. Reek 

Nature Chem. 2010, 2, 417-421 (News of the Week in C&EN 2010, April 5, p. 7)


Hypervalent Carbon Atom. "Freezing" the SN2 Transition State

S. C. A. H. Pierrefixe, C. Fonseca Guerra, B. van Stralen, J. N. P. van Stralen, F. M. Bickelhaupt 

Angew. Chem. 2009, 121, 6591-6593Angew. Chem. Int. Ed. 2009, 48, 6469-6471


A Ditopic Ion-Pair Receptor Based on Stacked Nucleobase Quartets

T. van der Wijst, C. Fonseca Guerra, M. Swart, F. M. Bickelhaupt, B. Lippert 

Angew. Chem. 2009, 121, 3335-3337Angew. Chem. Int. Ed. 2009, 48, 3285-3287


QUILD: QUantum-regions Interconnected by Local Descriptions

M. Swart, F. M. Bickelhaupt 

J. Comput. Chem. 2008, 29, 724-734


Aromaticity. Molecular Orbital Picture of an Intuitive Concept

S. C. A. H. Pierrefixe, F. M. Bickelhaupt 

Chem. Eur. J. 2007, 13, 6321-6328


Nucleophilic Substitution at Phosphorus (SN2@P): Disappearance and Reappearance of Reaction Barriers

M. A. van Bochove, M. Swart, F. M. Bickelhaupt 

J. Am. Chem. Soc. 2006, 128, 10738-10744


α-Stabilization of Carbanions: Fluorine Stabilizes more Effectively than the Heavier Halogens

F. M. Bickelhaupt, H. L. Hermann, G. Boche 

Angew. Chem. 2006, 118, 838-841Angew. Chem. Int. Ed. 2006, 45, 823-826


Hydrogen Bonds of RNA are Stronger than Those of DNA, But NMR Monitors Only Presence of Methyl Substituent in Uracil/Thymine

M. Swart, C. Fonseca Guerra, F. M. Bickelhaupt 

J. Am. Chem. Soc. 2004, 126, 16718-16719


Voronoi Deformation Density (VDD) charges. Assessment of the Mulliken, Bader, Hirshfeld, Weinhold and VDD methods for Charge Analysis

C. Fonseca Guerra, J.-W. Handgraaf, E. J. Baerends, F. M. Bickelhaupt 

J. Comput. Chem. 2004, 25, 189-210


C. Fonseca Guerra, F. M. Bickelhaupt ––– "Orbital Interactions in Strong and Weak Hydrogen Bonds Essential for DNA Replication" ––– Angew. Chem. 2002, 114, 2194-2197Angew. Chem. Int. Ed. 2002, 41, 2092-2095


The Short N-F Bond in N2F+ and How Pauli Repulsion Influences Bond Lengths. Theoretical Study of N2X+, NF3X+ and NH3X+ (X = F, H)

F. M. Bickelhaupt, R. L. DeKock, E. J. Baerends

J. Am. Chem. Soc. 2002, 124, 1500-1505


Chemistry with ADF

G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler

J. Comput. Chem. 2001, 22, 931-967


Kohn-Sham Density Functional Theory: Predicting and Understanding Chemistry

F. M. Bickelhaupt, E. J. Baerends

In: Rev. Comput. Chem.; K. B. Lipkowitz and D. B. Boyd, Eds.; Wiley-VCH: New York, 2000, Vol. 15, pp. 1-86


Charge Transfer and Environment Effects Responsible for Characteristics of DNA Base Pairing

C. Fonseca Guerra, F. M. Bickelhaupt

Angew. Chem. 1999, 111, 3120-3122Angew. Chem. Int. Ed. 1999, 38, 2942-2945


Understanding Reactivity with Kohn-Sham MO Theory. The E2-SN2 Mechanistic Spectrum and other Concepts

F. M. Bickelhaupt 

J. Comput. Chem. 1999, 20, 114-128